The 50 Most Slept-On Rappers of All Time

Hip-hop artists who haven't been given the props they deserve.

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Complex Original

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Underdog. Underrated. Undercover. Slept-on. Whatever you want to call 'em, there's a certain set of rappers out there that haven't been given the critical plaudits and/or hit success commiserate to their level of talent. And every dog (or dogg, or underdogg) deserves their day.

But don't get it twisted: This isn't a ranking of rappers in regards to their skill or talent. While everyone on this list has demonstrated undoubtedly impressive artistic aptitude at one point or another, we're judging "Greatest" and "Slept-On" by how slept-on these artists are, relative to the greatness of their respective catalogs.

There are MCs at the lower end of the list, like Nipsey Hussle, who don't necessarily have vast, essential discographies, but are far better than their level of popularity would ever suggest. At the opposite end of the spectrum, there are certified legends. Take guys like Big Pun, for example, who—sure—get their fair share of props.

But if you ask us? Not enough. Especially considering the sheer technical prowess that are irrefutable facts of guys like Pun that put him on par with any other revered great.

There's a dual criteria for being slept-on, and both scenarios are legitimate examples. Rappers arrive at these dilemmas for a number of reasons: label drama, jail, being too left-field, getting stuck in a local scene, and being overshadowed by another member of a group, for starters.

And another thing: Claiming to be slept-on is as hip-hop as break beats. Every rapper has a lowercase-c complex about being "the best," and when they're not recognized as such, talk of under-appreciation inevitably follows.

But: Some rappers who won't stop ranting about their "haters" do, in fact, have a point. Hell, plenty of MCs who are generally liked and never complain about being overlooked still deserve more praise than they've ever been awarded. It's time for that to change.

Here at Complex, we've been thinking about those slept-on rappers. From the respected vets whose legacies have diminished at an astonishingly accelerated rate, to the amazing artists who are, unfortunately, only known to a select few.

These are The 50 Most Slept-On Rappers of All Time...

50. Nipsey Hussle

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From: Los Angeles, CA
Signature Song: Nipsey Hussle "Bullet's Aint Got No Names" (2008)

When Nipsey Hussle first stepped on the scene he was hailed as the next big rapper out of L.A. There wasn't too much competition on the West Coast at that time, either. (It's a totally different story today.) Nipsey capitalized off his buzz with the excellent street single "Bullets Ain't Got No Name"—which showcased his knack for melody—and things got better for him when Game jumped on the remix.

Eventually his song "Hussle In The House" proved his songwriting skills and he started getting radio play in L.A. However, some of the overt gang references in the song led to protests and it was eventually pulled from the airwaves. Still, he made some strides by appearing on one of Snoop's albums and memorably hooking up with then-newcomer Drake for the excellent "Killers."

But since then, nothing much has gone right for him. All of his singles failed to connect and his album, Compton State of Mind, was indefinitely shelved, even though it was practically done and sounded pretty good. (We're some of the few people who actually heard it.) Eventually, he got dropped from his label Epic and he's struggled to build his buzz back, despite the fact that he's kept working hard and dropping material.

49. RA the Rugged Man

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From: Long Island, NY
Signature Song: R.A. the Rugged Man f/ Agallah "Til My Heart Stops" (1997)


It's not like R.A. doesn't have some great collaborations under his belt. Since he dropped a few tracks on Rawkus' Soundbombing series, R.A. has worked with the likes of Jedi Mind Tricks, Sadat X, and the Notorious B.I.G. He's shown how competent he is on the mic in a lot of his collaborations with his hazed-out vocals and controlled flow, but it's understandable how he's been lost in the shuffle (See: Biggie's verse on "Cunt Renaissance").

He's like the rap game Luc Longley, solid and consistent, but can't really compare to the Michael Jordans or Scottie Pippens. His upcoming LP, Legends Never Die, should bring some more Rugged heat, though, and it features MCs like Tech N9ne and Talib Kweli.

48. Andre Nickatina

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From: San Francisco, CA
Signature Song: Andre Nickatina "Smoke Dope and Rap" (1993)

 

A hero in his native Fillmore District of San Francisco, as well as a regional star throughout the West Coast, Andre Nickatina is known to most as the artist behind crossover cult hit "Ayo for Yayo," even though the song is more of a feature for fellow San Franciscan San Quinn. But Nickatina's catalog is deep, with two decades in the business and a career's worth of classic, unusual music.

Initially known as Dre Dog, Nickatina's first two albums both made some noise on Billboard. After his 1997 name change he released a series of records that would develop his cult fanbase, beginning with that year's Cocaine Raps, 1998's Raven in My Eyes. and 1999's Tears of a Clown. He was also a significant collaborator, releasing several records with San Fran rapper Equipto and helping launch the career of the Mob Figaz with the flawless Mob Trial compilation.

An unapologetically louche rapper with an eccentrically mannered flow, Nickatina's unusual musical choices are epitomized on his 2003 album Conversation With a Devil, when he first transitioned from Fillmore rap scene mainstay to dorm room stoner eccentric. The playful opening title track sets the stage for a record that alternates between Ren Faire production and bagpipes, a perverse, oddball sense of humor, and moments of genuinely intense revelation, like the harrowing morality tale, "Soul of a Coke Dealer."

47. E.S.G.

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From: Houston, TX
Signature Song: E.S.G. "Swangin' and Bangin'" (1995)

When Houston exploded on the national media scene in 2003, in part thanks to new-wave Houston rappers like Slim Thug, Chamillionaire, and the Swishahouse camp, it gave national exposure to a scene that previously had very little profile outside of the pages of Ozone and Murder Dog magazines. One such artist was Cedric Hill, better known as E.S.G., who came from Bogalusa, Louisiana. A member of the Screwed Up Click (S.U.C.), DJ Screw's conglomeration of South Side Houston MCs, E.S.G. was partially responsible for the spread of Screw music throughout the South in the 1990s. Although he was behind bars when Screw first started to gain prominence, he maintained a steady flow of albums for most of the last two decades.

A nasally flow and gangster subject matter dominate his records, beginning with 1994's Ocean of Funk (check out "If it Ain't One Thing It's Another," which reappeared in screwed format on DJ Screw's 1997 tape Chapter 45 100% Business) and 1995's classic Sailin' Da South. That record spawned many fan favorites, particularly "Swangin and Bangin," a hooky single that became one of the rapper's most well-known. Other tracks gained prominence thanks to Screw's mixtapes; his landmark 3 'N The Morning Part 2 prominently featured tracks from Sailin Da South mixed in with tracks from more well-known national artists like Dr. Dre, Warren G and 2Pac.

E.S.G. was also well-known for his freestyles for Screw's tapes; before T.I. and Lil Flip's beef was a national story, E.S.G. and Lil Flip became embroiled in a conflict over the title "Freestyle King" after Screw passed away, as each claimed the title. He came closest to the mainstream when Jimmy Iovine showed interest in the Boss Hogg Outlaws project E.S.G. worked on with Slim Thug; after the record did 100,000 in independent sales, major labels swooped in, but Slim Thug's relative youth made him the preferred pick and caused a rift between the two artists. E.S.G. has continued recording mixtapes and LPs throughout the 2000s; last year he released Owner's Manual, his 10th album.

46. Cashis

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From: Chicago, IL
Signature Song: Cashis "Lac Motion" (2007)

Before Shady 2.0, the original roster of the label featured a buzzworthy artist from Chicago. Ca$his would gain attention for his hard-hitting rhymes found on his early mixtape, Stars With Stripes. With lyrics that catered to the streets, Ca$his catapulted into the mainstream with a look alongside Eminem, 50 Cent and Lloyd Banks on "You Don't Know."

Although his solo EP, The County Hound, was a nice preview to his full-length album, he never really took off. As tough as Cashis' gangster raps were, he could not break out of the shadow of being Em's protégé. Eventually, he would create his own independent identity, but now with less of an impact than his Shady co-sign.

45. Starang Wondah

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From: Brooklyn, NY
Signature Song: O.G.C. "Hurricane Starang" (1996)

No one incorporated guns into their rhymes quite like Boot Camp. They weren't just rapping about guns, they saw themselves as guns letting off lyrical ammunition. Unlike Sean Price-who sulked in an almost failed rap career before becoming a NahRight favorite in the late 2000s-the Gunn Clappa Numba One Stagrang was never appreciated for what he brought to the table. He was one of the most fluid rappers in Boot Camp but was a member of O.G.C., the posse's lowest-selling crew. There are plenty of underground MCs who get their props from diehard fans. Starang deserves to be one of them.

44. Lil Boosie

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From: Baton Rouge, LA
Signature Song: Lil Boosie "Top To the Bottom" (2010)

"It's time to introduce Lil Boosie Boo or should I say Lil Boosie/The one who rap bout killin', shootin', and marijuana distribution." So began Lil Boosie's scene-stealing verse on South Coast Coalition's "Livin' What I'm Spittin," a song title that could also serve as a statement of purpose for Boosie's brand of "reality rap."

Although he's had dalliances with the pop charts, like a guest spot on Foxx's "Wipe Me Down," Boosie's strength is in a catalog that he spent the bulk of the 2000s building, until his arrest on gun and drug charges in 2009. His scratchy vocals and gripping delivery cut through the noise on every track he appears on, and helped make him a fan favorite on the southern touring circuit, depicting himself as a man of the people and a gun-toting drug trafficker unafraid to shoot, fighting murder cases while buying food and toys for local children in his neighborhood.

Epitomizing the schizophrenic tensions latent in all gangster rap, Boosie seems to understand, intrinsically, the resonances that drive hip-hop's street audience. He lashes out against corrupt police ("Fuck The Police"), laments duplicity with particularly visceral anguish (Betrayed ") and explores the darkest side of his own psyche ("Mind of a Maniac"). It's compelling drama, made moreso by the lines between fact and art that his music so often disregards.

43. Casual

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From: Oakland, CA
Signature Song: Casual f/ Del tha Funkee Homosapien & Pep Love "Who's It On" (1994)

In terms of pure rapping skills alone, the Hieroglyphics crew has earned its place in hip-hop history. Even though Del Tha Funkee Homosapien's baritone makes him the most recognizable MC in the bunch, it's Casual whose talents have always been equally clear, but sometimes overlooked. His influence runs deeper than you might think, too-you can find his face among other greats on the Midnight Marauders artwork. He might not ever top his 1994 debut, Fear Itself, but who cares? He's given us a classic and a discography full of strong and diverse listens. Salute that man.

42. Playa Fly

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From: Memphis, TN
Signature Song: Playa Fly "Nobody Needs Nobody" (1998)

Memphis legend Playa Fly has been rapping in the city's underground scene for going on two decades. He made a name for himself in the early '90s but his career seemingly took off when he got with Three 6 Mafia. Unfortunately, after recording one album with the group, he had a falling out with them because...well it's Three 6 Mafia, and they always have a falling out with new members. (Crunchy Black, anyone?) Despite that, Fly went on to record more material and release a series of albums (he also had a memorable diss record called "Triple Bitch Mafia"), but he remained an underground sensation and never got national exposure on the level of Juicy J and DJ Paul.

41. The Jacka

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From: Pittsburg, CA
Signature Song: The Jacka f/ Andre Nickatina "Glamorous Lifestyle" (2009)

In the mid-1990s, C-Bo was a rising California gangster rapper. While his career slowed in the next decade, a group he helped introduce to the music industry would go on to transform Bay Area rap music. Although the Mob Figaz (a group consisting of Rydah J. Klyde, Husalah, Fed-X, AP-9 and The Jacka) were largely under the radar during Hyphy's big moment in the mid-2000s outside of California, Jacka's 2005 release The Jack Artist established that there was much more going on in the Bay than manic Rick Rock beats and kids being irresponsible with automobiles.

The Mob Figaz, by contrast, were more concerned with adding onto Cali's street rap tradition and incorporating an East Coast influence; they had come of age in the late 1990s, when the Bay's scene was widely considered to be faltering and New York was ascendant.

The Jacka in particular has a laid-back, smooth flow reminiscent of influences like Big Daddy Kane, Slick Rick, and Special Ed, mixed with the more militant West Coast influences of Kam and Ice Cube, filtered through his own conversion to Islam. He also had an unusual ear for beats, incorporating reggae samples and production that hearkened back to New York's pop-rap peak in the early 2000s. From 2005 through 2009, he released a series of records, both solo and as a member of the Mob Figaz, culminating in 2009's epic Tear Gas.

Most compelling was how he addressed violence, keeping his moral conscience intact while nonetheless remaining fundamentally a street-oriented artist. Unfortunately, the media backlash after Hyphy worked against his crossover; a subsequent lack of interest in Bay Area rap music remanded him to the post-Mac Dre touring circuit from the Bay to Kansas City.

40. Jean Grae

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From: Cape Town, South Africa
Signature Song: Jean Grae "My Story (Please Forgive Me)" (2008)

Enter: Jean Grae. A modern day female rapper who actually raps about the plight of being a woman. Formerly known as What? What?, Jean's career has mostly been defined by false starts. She hit the underground scene in the late '90s, dropped a well-received debut album in 2002, Attack of the Attacking Things, which started building her buzz and getting attention.

Then she teamed up with 9th Wonder and crafted the wonderful, underrated Jeanius. The album leaked on the Internet in 2004 and for whatever reason, Grae went into a hiatus for a few years until the album was officially released in 2008. Her career hasn't improved much since then.

It's too bad because Grae is such a rare talent, armed with an off-kilter flow that always keeps you guessing and the vocal tenacity to shove unbelievable amounts of syllables into a sentence. Plus, she's great at baring her soul. For proof, peep the dark and twisted, "My Story," where she details an abortion, a miscarriage, and a failed suicide attempt.

39. Bubba Sparxxx

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From: LaGrange, GA
Signature Song: Bubba Sparxxx f/ Timbaland "Deliverance" (2003)

Bubba Sparxx's misfortune wasn't just that he was a white rapper, it's that he was the first significant white rapper post-Eminem. However, Bubba quelled all comparisons to Slim Shady with his first single, "Uglym" which really no other rapper but Bubba could have made and nobody but Timbaland could have produced.

His debut album, the often forgotten Dark Days, Bright Nights, not only went gold but established him as a backwater rapper with backpacker sensibilities and mainstream potential. He embraced his country roots and the lives of impoverished white folks long before Yelawolf took that aesthetic and ran with it. "Did you know they closing down the only factory in this town?/And still you got the nerve to say there's plenty work to go around?" he asked on "Well Water."

Bubba (along with Timbo) hit his stride on his second album, Deliverance, making the best album of his career. Sadly, fans didn't seem to care and as time passed, Bubba slipped into irrelevance. Maybe what he said on "Nowhere"-a song that he eloquently communicates his fears-actually happened. He just vanished "in the vapors of the plague the South has suffered from."

38. Ka

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From: Brooklyn, NY
Signature Song: Ka "Decisions" (2012)

Ka may be a relic of bygone era but his strength lies in the fact that he doesn't pretend to be anything else. A fan of "real hip-hop" (read: '90s rap) he makes music that reflects that aesthetic to a T even in 2012. He basically looks, sounds, and raps like a hip-hop dinosaur, but come on dude, a Triceratops is pretty awesome. And with everyone complaining about how the '90s had such better rap music than today, what's wrong with a contemporary rapper with a throwback aesthetic? Let's hope his recent release, Grief Pedigree, will wake folks up.

37. Esham

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From: Detroit, MI
Signature Song: Esham "KKKill the Fetus" (1993)

It's hard to say that Esham should be more mainstream; his horrorcore is resolutely opposed to anything resembling mainstream values, openly embracing and making a mockery of anything resembling good taste or respect for those who are victimized. It's a kind of spectacular, exaggerated therapy, an attempt to find the darkest possible places. But Esham reminds us that while we don't always like rappers the cross the line, rappers that go wayyyy past the line are kinda awesome

36. Peedi Crakk

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From: Philadelphia, PA
Signature Song: Peedi Crakk f/ Beanie Sigel, Freeway & Young Chris "One for Peedi Crakk" (2003)

Philly spitter Peedi Crakk came in the game during the height of Roc-A-Fella and State Property's reign in the early 2000s, making his mark murdering mixtape cuts with his Chain Gang brethren, and appearing on Jay-Z's Blueprint 2. His undeniable solo slammer "One For Peedi Crakk" showcased his high-energy, staccato-style street skills, and he stole the show on Freeway's "Flipside," a song that still rings off in the club.

Unfortunately, Peedi's solo project never came out, which led to him throwing some shots at Hov on wax. Then he got locked up, putting his career on hold indefinitely. In 2012, he's a free man again, and still the same dangerous MC he always was, with a fiery flow that just needs the right packaging. Here's hoping he can actually release an album titled Camel Face Hunting Season.

35. A.G.

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From: Bronx, NY
Signature Song: Showbiz and A.G. "Fat Pockets" (1992)

Long before Peter Gunz and Lord Tariq reminded us, "If it wasn't for the Bronx, this rap shit wouldn't be going on," A.G. was holding it down for the Boogie Down. Along with his partner Showbiz, A.G. put on for his borough with one of the most distinctly New York rap flows ever.

A.G. not only sounds like he's never heard West Coast hip-hop, he sounds like he's never even heard of California. A Bronx Bomber to the death, he became one of the few regional heros of New York thanks in part to his myopic worldview. He might have seemed closed-minded to some, but to diehard fans of East Coast hip-hop he was simply awesome.

34. Killarmy

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From: Staten Island, NY
Signature Song: Killarmy "Fair, Love and War" (1997)

Wu-Tang had so many damn affiliates we're not even mad at people for forgetting about Killarmy—a crew that basically existed because RZA used to get it in in Ohio before blowing up in the rap game. Them being slept-on isn't a shock to us at all, especially because their first album, Silent Weapons for Quiet Wars, wasn't too well received.

But they stepped it up in a major way on Dirty Weaponry and they deserve more respect than they usually get. What made Killarmy dope was how they thematically unified their style around military themes and sprinkled in 5 Percenter teachings. Their stylistic influence notwithstanding, they definitely weren't Wu-Tang-but that doesn't mean they weren't a worthy offshoot of the crew.

33. Obie Trice

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From: Detroit, MI
Signature Song: Obie Trice "Cry Now" (2006)

Coming up under a hip-hop legend (or legend in the making) might seem like a great idea at the time, but being viewed as a sidekick can clearly have its downsides. For Obie Trice, that meant gaining instant exposure through a sample on Eminem's "Without Me," catching a heavy buzz (no pun intended) with a stellar debut in Cheers, and watching his spotlight fade because of a lack of promotion.

While Trice would eventually leave Em's Shady Records on good terms in 2008, that departure wasn't without its detriments. It wasn't until this past April that he released Bottoms Up, a proper follow-up to 2006's Second Round's on Me. The album might have received generally strong reviews, but most heads were turned when they saw Eminem's name on the guest and producer credits.

What's most frustrating about that point is the fact Em and Trice's collaborations weren't on some "murdered you on your own shit." They complemented each other and, in a perfect world, Trice would get the credit he deserves for that.

32. Rah Digga

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From: Newark, NJ
Signature Song: Rah Digga "Imperial" (1999)

 

When Eve was a hot new female rapper in the late '90s/early 2000s, she was dope, but it's the criminally underrated Rah Digga who deserves way more attention then she ever got. Listen to any Digga verse and you'll see she's a spitfire MC who style obviously derives from legends like KRS-One and Kool G Rap, plus she had plenty attitude and wit to along with it. Her 1999 debut, Dirty Harriet, received some good press but failed to go gold. She didn't help matters by not releasing another album until 2010's completely ignored Classic.

31. Young Bleed

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From: Baton Rouge, LA
Signature Song: Young Bleed f/ Master P & C-Loc "How Ya Do That" (1998)

Young Bleed wasn't the flashiest member of the No Limit army. He didn't have the exuberant dexterity of Mystikal or the outsized charisma of Soulja Slim. But the Baton Rogue, L.A .resident was more of a subtle artist. His tasteful, laid-back drawl unfolded like a proto-Curren$y.

This laconic style found a home with the Concentration Camp, an unfortunately-titled crew that included rappers C-Loc, Max Minelli, and later on, a young teeanger known as Lil Boosie. When Master P remixed C-Loc and Young Bleed's "How You Do That," adding his vocals to the mix for 1997 I'm Bout It soundtrack, it became the number-one song on Billboard's R&B/Hip-Hop charts the following year.

That year he released his solo debut, which went gold; his follow-up release, My Own was almost as accomplished, and highlight "Give and Take" still showcased his slick, casual style which was street-oriented in content, but always with a reserved, effortless appeal.

He continued recording through the 2000s, which brought independent albums Rise Thru da Ranks although he never again approached the level of success that he had with No Limit. 2011's Preserved found the rapper collaborating with new artists, when Bleed signed to Tech N9ne's Strange Music, and long-YouTube-only track "Put Your Stamp On It" finally saw wide release.

30. Black Rob

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From: Yonkers, NY
Signature Song: Black Rob "Star in da Hood" (2005)

On Harlem World Ma$e rhymed, "See the moral of the story is/I'm not here to replace Notorious." Now that's a line we can appreciate because, let's face it, after Biggie died and Mase flew the coop, Puffy was in the hunt for a replacement that simply did not (and will never again) exist.

So Puffy did what he could and put out Black Rob. A streetwise rapper with a smooth flow, Rob scored a huge hit with "Whoa!" That turned out to be both the best and worst thing ever to happen to his career. It made people think Rob was a one-hit wonder who lucked out by getting on a crazy Buckwild beat. Rob's career stalled when he released little to no material and did a stint in jail, but that didn't change the fact that he was a strong rapper capable of spitting thoughtful rhymes.

Check his bars on "Star In The Hood" ("Lot of old dudes used to work my block, they on Lenox Ave now selling t-shirts and socks/Pushing everything they own in a shopping cart, so I throw'em a little something because it hurt my heart.") He could also craft a wild narrative, as he did on Puffy's "I Love You Baby"-who can forget his line "Run out of ammo, started throwing bottles"?

The only thing we're not sure about is his reference to "the Tavern on the Green robbery in '86" on Ma$e's "24 Hours To Live." Did that really happen? Because it sounds wayyy too specific not to be real-and we wouldn't put anything past Black.

29. Proof

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From: Detroit, MI
Signature Song: Proof "Kurt Kobain" (2005)

Trust us, this is not a case of dead rappers getting better promotion. Proof is on this list for two reasons. First, he was an incredibly influential member of Detroit's thriving underground scene where-before blowing up-he hosted (and participated in) batte-rap competitions including battles at Detroit's legendary Hip-Hop Shop. Proof was the inspiration for the character Future in 8 Mile, who was portrayed by Mekhi Phifer.

The second reason Proof is on here is for his work on D12's underrated debut, Devil's Night. True, the main reason we love that album is because Eminem was absolutely on fire at the time, but the best song on the album, "That's How," doesn't even feature an Eminem verse.

As Mr. Porter once told us, "That [album] was Proof and Em. They masterminded that whole D12 project." And don't sleep on Proof's debut, Searching For Jerry Garcia, an album obsessed with deceased musicians-which Proof would tragically become himself.

28. Akinyele

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From: Queens, NY
Signature Song: Akinyele "Put It in Your Mouth" (1996)

Akinyele wasn't the first rapper to make ignorance an artform, but he was one of the best. He's been overshadowed a few times, first by a Nas guest spot on "Live at the BBQ." Then by his biggest hit; "Put It In Your Mouth," a relentlessly catchy, extraordinarily subtle sexual suggestion, the song overshadowed the then-budding rapper from Queens, New York.

None of his other material attained that level of success and he's known to mainstream America as a particularly lewd one-hit wonder. But he's known to hip-hop heads as a particularly lewd character with a solid discography, a distinctive rap style, and an amusing, over-the-top-albeit frequently offensive-lyrical approach.

On his debut, a tribute to gynecological health entitled Vagina Diner, he was matched with one of the best producers of his era, Large Professor. Xtra P's gift for early '90s sample-based beats were at their zenith on this record, from the wirlitzer-laced "I Luh Her" to the "Psychedelic Shack"-sampling "Outta State." And from his distinctive barked delivery to concept tracks about dealing with pregnancy (poorly), avoiding exercise, and being a passive aggressive, controlling boyfriend ("No Exit"), Akinyele was a unique case of how great art can be made from very, very bad ideas.

27. Memphis Bleek

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From: Brookyln, NY
Signature Song: Memphis Bleek f/ Jay-Z, Missy Elliott & Twista "Is That Your Chick?" (2000)

He couldn't have foreseen it at the time, but starting his career on a Jay-Z album was, in some ways, a seal of fate for Memphis Bleek. Of course, Bleek's loyalty to Hov has earned him lifetime millionaire status, but it's also the reason why he's totally dismissed as a rapper and seen as the GOAT weedcarrier.

At the turn of the century, he showed promise with solo hits "Do My...," "My Mind Right," and "Is That Your Chick?"-at the same time, Jay's career was reaching unprecedented heights. As a result, Bleek's efforts were overlooked. Since then, he's just been tagging along for the ride. The standout record on his last album, 534, was a Jay-Z song, "Dear Summer."

26. Young Dro

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From: Atlanta, GA
Signature Song: Young Dro f/ T.I. "Shoulder Lean" (2006)

Young Dro's 2006 debut album is about as good as a 2000s rap album could get. Dro had a distinctive flow, lyrical flair-particularly for seafood-a sense of humor, a tough baritone, and seemed destined to follow T.I. to greater glory, much like Waka would follow Gucci some years later. Instead, after a cult classic debut and a few scattered follow-up singles (Grand Hustle compilation track "Grand Hustle Mafia" remains one of his most slept-on contributions) he seemed to miss more than he connected.

His collaboration with Yung LA ("Ain't I") was a great track, but his affiliation with the burgeoning swag rap movement didn't seem to give him much footing. Successive mixtapes have featured a few scattered gems-this year's "How You Feel" is a minor summertime anthem, and "Freeze Me" with Gucci and T.I. was a modestly successful single. Perhaps the quality of his debut stacked the cards against him, but overall, as that record retreats further in the rear view, it seems like his career feels like one of missed opportunities.

25. PMD

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From: Long Island, NY
Signature Song: PMD "I Saw It Cummin'" (1994)

PMD is a classic case of being overshadowed by his partner, Erick Sermon, who umm... once tried to have him killed (seriously, watch Beef II). Although EPMD is recognized as a legendary group and Sermon went on to have a successful solo career, PMD's efforts arelargely forgotten. Moreover his contributions to EPMD are largely slept-on. It's true that the duo didn't rhyme about much (mostly sex, money, and dissing other rappers) but PMD put together strong verses, even if he didn't deliver them with enough thump to get people's attention.

24. Sheek Louch

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From: Brooklyn, NY
Signature Song: Sheek Louch f/ D-Block & J-Hood "Mighty D-Block (2 Guns Up)" (2003)

While his D-Block brethren Jadakiss and Styles P are great rappers who never made classic albums, Sheek has made a career of simply making hard records. While Jada tried to please every crowd and make major label money, Sheek went independent and put out albums like, After Taxes-gritty affairs that were light on filter but heavy on street appeal.

Plus Sheek never ever got any props for hilarious punchlines like, "My semi leave you chestless/So there ain't shit you can say to me when you be breathless" and "I'm hot like lava/We got sons in the game and we don't need Maury to know who the father." And our all time favorite: "He clapping at you, you ducking, making you dance/You shoulda spend it on some guns instead of Iceberg pants." How can you front on lyrics like that?

23. Wise Intelligent

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From: Trenton, NJ
Signature Song: Wise Intelligent "Shitty Inna City" (1996)

Was it because they lacked that one classic single? Or because of their insistence on repping 5 Percenter ideology? Or because their names were corny and a bit pretentious? Maybe it was a little bit of all three, but the fact is that Poor Righteous Teachers remain one of the most unappreciated acts in hip-hop history.

Coming up in an era where "underground" acts like Gangstarr, A Tribe Called Quest, and Brand Nubian all thrived, PRT dropped thoughtful yet fun albums like Holy Intellect and Pure Poverty but got little love for it back then, and virtually no love for it today. The group's frontman Wise Intelligent went on to have a solo career that hardly anyone remember, although his creative legacy lives on if you know where to look. Poor Righteous Teachers remind us that being smart and ernest in the '90s took you nowhere.

22. Mac Mall

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From: Vallejo, CA
Signature Song: Mac Mall "Sic Wit Tis" (1993)

Vallejo rapper Mac Mall is one of hip-hop's most underrated talents because his star burned brightest in its earliest stages. His debut album, Illegal Business, was released on Khayree Shaheed's Young Black Brotha label. (Khayree was also the album's producer, and was responsible for much of the production on Mac Dre, Ray Luv and Young Lay's LPs, as well as doing most of the beats on Vanilla Ice's debut LP.) Mac Mall had other friends in high places; his single My "Ghetto Theme," a hard-hitting narrative about the tragic realities of gang life, received a Tupac Shakur-directed video. "Sic Wit Tis" fell more in line with the album's overall sound, its squealing production a perfect framework for Mac Mall's fluent rap style.

The album moved 200,000 units independently, leading to a deal with Relativity Records. The label released his sophomore record, Untouchable in 1996; it reached No. 6 on the R&B/Hip-Hop charts and No. 35 on the Billboard 200. This would be Mac Mall's biggest moment, both commercially and critically. He continued recording into the 2000s, but despite two of the most promising records in West Coast rap history, never achieved the level of success many expected.

21. Tha Liks

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From: Los Angeles, CA
Signature Song: Tha Liks "Only When I'm Drunk" (1993)

We're never surprised when preachy conscious rappers don't sell too well. Let's face it-they can get annoying. But it's a mystery why Tha Liks never sold since they were basically party rappers who rapped about "hoes, flows, and 40 oz." and dropped laugh-out-loud lines like, "I'm lookin' for the hoes that got some sex I could borrow/I'll gladly pay you back next Wednesday the 3rd/Why you laughin' at me baby? That's my motherfuckin' word."

Can someone please explain to us why it's 2012 and it feels like Tha Liks never even existed? Sure, the group has long since broken up, but think about it: when was the last time you heard their name brought up a rap convo compared to contemporaries like The Pharcyde? What makes it all the more frustrating is that Liks had several quality albums, a classic single with "Hip-Hop Drunkies" Even Tash's solo album, Rap Life, is pretty damn good. Maybe it's just a case of learning a bit too much from your mentors-they were ushered into the game by King Tee who also finds himself on this slept-on list.

20. Soulja Slim

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From: New Orleans, LA
Signature Song: Soulja Slim "From What I Was Told" (1998)

Soulja Slim was a hero in New Orleans; originally a member of the Parkway Pumpin' label, James Tapp-who was then known as Magnolia Slim, named after the Magnolia Projects where he grew up-released his debut in 1994. Parkway Pumpin' was a magnet for New Orleans talent; founded by KLC (who went on to become a key member of Master P's Beats by the Pound production crew) and his friend Dartanian Stovall, the label attracted future No Limit mainstays Mac, Mr. Serv-On, Fiend, Mystikal and Da Hound. Slim was the only one of that group to release a record (1994's Soulja Fa Lyfe) before everyone was picked up by Master P. Soulja Slim's Give It 2 Em Raw was released in 1998, went multi-platinum and debuted at #13 on Billboard's Hot 200.

His appeal was all about raw realness. Slim possessed an otherworldly confidence rooted in the streets, as epitomized in the opening lines of his prophetic single "From What I Was Told": "I'm gonna hit No Limit like Pac hit Death Row and make money out the asshole / and blow up, like the World Trade, and be protected by No Limit tanks, soldiers with K's and hand grenades." After three years behind bars on an armed robbery charge, Slim emerged in a new No Limit landscape: nearly all of Master P's roster had deserted the company, some alleging unfair business practices.

After releasing 2001's The Streets Made Me, Slim too split from No Limit, launching his own Cut Throat Comitty record label. He released Years Later in 2002, and Years Later...A Few Months After the following year, both of which featured the harrowing KLC-produced "Souljas on My Feet," an uncompromising bit of Nolia noir. Soulja Slim's collaboration with Juvenile, "Slow Motion," raced up the charts soon after its release, but unfortunately Slim would not live to enjoy its success; he was shot to death in front of his grandmother's home on the night before Thanksgiving, 2003.

19. Z-Ro

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From: Houston, TX
Signature Song: Z-Ro "The Mo City Don" (2008)

Z-Ro is about as popular as a regional rap star can get without becoming a crossover artist, and his fans are some of hip-hop's most devoted. Like an archetypal lone cowboy, the rapper's old soul lyrics and heavy subject matter have made him a favorite in and around Texas. He is the living embodiment of gravitas, a true people's hero who picked up where Scarface's depressive gangster tales left off. At once assertive and vulnerable, he often seems beset by tragedy. His resonance with local fans exemplifies exactly how slept on he is outside of his home state. Check this concert footage, where the audience recites the entirety of his "Mo City Don" freestyle back at him.

18. Suga Free

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From: Pomona, CA
Signature Song: Suga Free "Why U Bullshittin'?" (1997)

DJ Quik affiliate Suga Free is one of the most distinctive and personality-drenched rappers in history. Born Dejaun Rice, the Oakland-born Compton-MC released a debut that is considered by many hip-hop heads to be one of the finest records of all time. Quik once bragged that the album was recorded in a garage, but sounded like it did because he was My "such a great fucking engineer." He's not lying, but for all the wonders that DJ Quik worked behind the boards, it was still Suga Free's show. The verbose pimp-rapper extraordinaire is a rhythmic wizard, spitting dense anecdotes splashed with humor, ignorance, drama, and genuine insight.

At once a caricature and a master technician, he managed to make all his morally fraught chest-beating seem completely human; witness the record's most moving moment, the heart-rending "Dip Da." But mostly, he's funny; he's had several subsequent albums and some My can't-miss singles. Almost every guest verse is an event, so much so that both volumes of his Features compilations are worth browsing, if only for lost gems like Odyssey-sampling "Inside Out" and the disco remix "Pimpin in the Year 3000," whose title speaks for itself.

17. Kilo Ali

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From: Atlanta, GA
Signature Song: Kilo Ali "Hear What I Hear" (1992)

Originally known simply as Kilo, Kilo Ali released a series of albums starting in the early 1990s and became a hero to Atlanta bass aficionados and Freaknik attendees alike. A charismatic vocalist, Kilo's smooth delivery and subtle rhythmic sense-simultaneously energetic-yet-casual-stood apart. He had a distinctive style, even when dominating the brashest bass production. He was also funny; look no further than the pro-cunnilingus sex jam "She Got Me Eating Pussy" (best heard with its original, un-cleared Anita Baker-sampling intro) or his ahead-of-its-time slang experiment "The Piz," which predates Calvin Broadus' popularization of Snoopspeak by several years. Kilo's influence has been profound; look no further than Gucci Mane's nonchalance-over-club-banger style. Waka Flocka has also cited him as a major inspiration.

16. Juju

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From: Queens, NY
Signature Song: The Beatnuts "Do You Believe?" (1997)

The Beatnuts' catalog is underrated in general but Juju's work is especially slept-on. He was the better rapper of the duo (sorry Psycho Les) and had plenty of worthy quotables like, "Listen to me, it's better to be/Lying dead with honor, soldier, than to never be free." And "Ayo it's ill when I'm heated how my heart stay cold." It was probably the Beatnuts lo-fi, unpolished sound that prevented them from becoming bigger than they were, but here's hoping more hip-hop heads will take notice of JuJu's lyrical stylings. He may not have the platinum plaques, but at least he deserves the props.

15. Group Home

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From: New York City, NY
Signature Song: Group Home "Supa Star" (1995)

Even though Group Home's debut album, Livin' Proof is acknowledged as a classic, neither Lil Dap or Melachi the Nutcracker have ever received any credit for what they brought to the table. Rap fans refused to acknowledge that they were good rappers, instead attributing all the group's success to DJ Premier's outstanding production. Of course, Preemo didn't hurt-and they floundered without him on their second album-but that doesn't mean that they were unworthy of his beats. Quite the opposite, Dap's voice is unmistakable and Melachi's flows were always on-point. We all know Premier is incredible, but can we please give Group Home a break?

14. Tim Dog

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From: Bronx, NY
Signature Song: Tim Dog "Fuck Compton" (1991)

Before Dateline exposed him for running an online dating scam (SMFH), Tim Dog was one of the most hardcore rappers ever. His debut album, Penicillin on Wax, was basically one big fuck you to the entire West Coast. Tim might not have been the cleverest rapper, but he was certainly one of the most brash and uncouth. And while his sales might have been lackluster, he made enough of an impact to elicit responses from Dr. Dre, DJ Quik, Compton's Most Wanted, and more.

13. Young Zee

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From: Newark, NJ
Signature Song: Young Zee "That's My N**** fo' Real" (2002)

While PaceWon received considerable acclaim as a member of the under-rated New Jersey clique The Outsidaz, it's Young Zee's high-pitched, comedic flow that feels most sui generis today. He had several shots at breakout moments: he appeared on The Fugee's massive sophomore LP, The Score, and claimed to have written many of Pras's lyrics on the record. He had a Lauryn Hill-featured single. He appeared on 8 Mile, one of the best-selling hip-hop soundtracks of all time, with "That's My Nigga For Real." And he released records with both The Outsidaz and as a solo artist, with the support of a major label.

He also dealt with label drama, failed to connect with a fanbase (something that he might have found much more easily in the Internet era), and eventually became one of hip-hop's most slept-on artists. An indisputable influence on Eminem, Zee mastered a style that seemed to draw particular attention to each punchline, circling in on itself in a way that compelled the listener to hang onto each lyric.

12. Cormega

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From: Queensbridge, NY
Signature Song: Cormega "They Forced My Hand" (2011)

There's no way to talk about Cormega without talking about Nas. Nasir gave Mega his start by letting him get on "Affirmative Action." The success of that song led to the formation of The Firm but for whatever reason, Cormega ended up getting kicked out of the group. Since then, he's remained rather salty about the whole affair. Regardless, his first two albums The Realness and The True Meaning were hailed as underground classics and praised for Mega's intricate rhyme schemes-even if every single song sounded like he was taking shots at Nas.

11. King Tee

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From: Compton, CA
Signature Song: King Tee "Bass" (1988)

If you don't know that King Tee is one of the West Coast's most important artists, you better ask somebody. Emerging as one of Compton's earliest hip-hop heroes, the rapper's 1988 debut, Act A Fool, was widely considered a hip-hop classic. In the late 1980s and early 1990s, he worked primarily with producer DJ Pooh, and was responsible for the rise of the Alkaholiks, whom he helped guide into the industry.

According to Ice T, King Tee was a formative influence on the Notorious B.I.G. He was also a member of the Likwit crew, a conglomeration of Los Angeles artists that included Xzibit, who would bring Tee into Dr. Dre's orbit. At one point the Cali rap pioneer was considered one of the most respected West Coast rappers, but he failed to gain the national attention most expected him to get. After releasing three more albums on Capitol, Tee left to join Dr. Dre's Aftermath label. Numerous delays and a chronically delayed album made him leave, only to release the Dre-helmed record Thy Kingdom in 2002 to minimal attention.

10. Max B

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From: Harlem, NY
Signature Song: Max B "Why U Do That" (2008)

Max B's story is a particularly tragic one. Often credited with writing a bulk of Jim Jones mid-decade material, the Harlem rapper was one of New York's true grassroots success stories in the latter half of the 2000s. Just when he seemed to be breaking through, his 2006 arrest and subsequent 75-year-prison sentence marked the end of a promising career.

What made Max's music so mesmerizing wasn't just his ability to flood the streets, but his unique musical approach. Adopting the melodicism of 50 Cent and fleshing it out with the character of a drunken street-corner poet, his raspy, grungy singing style gave his music a wistful, intoxicated feel. At once a songwriter and a rapper, he instilled his tracks with a distinctive character that was wholly his own and gave New York rap a more universal street appeal at a time when it was drifting further from hip-hop's mainstream, Max B's druggy melancholy creating the atmosphere as much as Dame Grease's dilapidated production style.

Like many artists in the latter half of the 2000s, the mixtape trade was where he refined his sound and released his best material. Both as a member of Byrdgang and as a solo artist, his mixtapes are more likely to define his legacy than his one-off album, released in 2011 while he was behind bars. His profile has continued to rise, even as he remained behind bars helping to propel the career of his sidekick and Bad Boy signee French Montana.

9. Nature

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From: Queens, NY
Signature Song: Nature f/ Nas "The Ultimate High" (2000)

Nature's rise to forefront of hip-hop was about as controversial as possible. He's the one who infamously replaced Cormega in The Firm after Mega and Nas fell out. Unfortunately, the album was too much of a creative failure for anyone to care about what Nature had to say. Still, he gained a strong buzz off the album. His solo debut, For All Seasons, dropped about eight seasons too late even if it had bangers like the Nas-assisted "Ultimate High." But by then no one cared as much as they would have a few years prior. We're willing to argue that if Nature's debut had dropped in either 1998 or 1999, he wouldn't be such a slept-on rapper.

8. Malice

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From: Virginia Beach, VA
Signature Song: Clipse f/ Jadakiss, Styles P & Rosco P. Coldchain "I'm Not You" (2002)

In an interview with Karen Civil, Pusha T once explained the Clipse's chemistry: "The dichotomy of the Clipse is one of those things where Malice is more of the thinker and the introspective one and I'm usually known as the wordplay one or the one who is a bit more brash." That about sums it up, though we'd add that Pusha's flow is simply wicked. But as much as we love Push, we have to admit that Malice made Clipse a dynamic duo because he was their conscience in an era where so few rappers had one.

Compared to his little brother, Malice sounds like an old-school rapper. In fact, Malice is much older than you think. How old? He's so old he fought in war in Iraq-the first one! Similar to GZA, Malice wasn't ahead of his time-he was behind it.

But he didn't blow up past his expiration date, instead he aged like fine wine. His cerebral lyrics, often loathing the ugliness drug game, made him one of the most unique rappers of his era. By the mid-aughts, most coke rappers were boasting about moving kilos and flossing chains with little regard for the suffering their actions caused. But Malice often rapped about what Ice-T refers to as "the b-sides of the game"-the darkness that came with selling a product that's akin to selling your soul.

It's no wonder that Malice's best verses were always delivered at the end of Clipse's projects-his was the voice you heard at the end of the day, when your cash has been counted but your sins haven't. On "Ultimate Flow" he laments, "All the money in the world, and I ain't fulfilled." On "Nightmares" he reasons, "They be thinking nice car, nice crib/I be thinking how long will these niggas let me live?" But for his finest moment, look no further than "I'm Not You," which serves as a mission statement for the group. "Deepest regret and sympathy to the street/I see them pay for they fix when they kids couldn't eat (so sorry)/And with this in mind, I still didn't quit/And that's how I know, that I ain't shit."

Pusha may be the one who rides around shining, but it's Malice who has the nightmares. We're hoping he can get his head right and get back in the game because as the OG Ice-T once explained, "There's an entirely other side that only hustlers know about. I would always look at people's music and if I didn't hear that [b-side], then I knew it was fake." We'd describe Malice's music as nothing but the b-side. How real is that? EGHCK!

7. Large Professor

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From: Harlem, NY
Signature Song: Large Professor "Ijuswannachill" (1996)

Although he's widely credited as a dope producer behind the boards, Large Professor is barely acknowledged for his skills behind the mic. But Xtra P's pen game is unquestionable for his work on Main Source's Breaking Atomsalone. If you don't believe us, just peep records like "Just A Friendly Game of Baseball," which combines a baseball theme with a not-so-subtle tale of police brutality that's as damning as it is inventive.

His legacy may have been tarnished by his tendency to disappear for long stretches. Shortly after Breaking Atoms dropped, Main Source broke up and P went solo. And although he did help mentor Nas in the early part of his career and went on to produce for everyone from Rakim to A Tribe Called Quest, P didn't put out too much solo material. His first solo album, the underappreciated 1st Class, didn't even drop until 2002. But hey, at least the album had awesome cuts like "Stay Chisel" on it.

6. Mac Dre

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From: Vallejo, CA
Signature Song: Mac Dre "Feelin' Myself" (2004)

Mac Dre's story is most memorably chronicled in an episode of BET's American Gangster series that was technically about the Pizzeria/Bank Robbery clique known as the Romper Room Gang. But since Mac Dre's legend was the most compelling part of the story, the show's producers focused on the rapper as their star, even though he was considered a tangential part of the gang's criminal escapades (though it should be noted that he did bait police officers by name in song and mentioned the name of an informant in a jailhouse call to KMEL radio). But leaving all that other stuff aside, he was truly an amazing rapper. A charismatic, gifted lyricist with an incomparable sense of humor, Mac Dre became one of the biggest stars in California rap history.

After his release from prison in the late 1990s (he received a 5-year federal sentence when the FBI caught the Romper Room Gang planning a bank heist), Mac spearheaded the Bay's hyphy movement and helped spread the scene on a touring circuit from California throughout flyover country, pushing to the East as far as Kansas City. To this day, Bay Area rap has a strong hold on sizable portions of the Midwest, largely thanks to his efforts. While many critics reduced "hyphy" to a buzzword for a production style and the antics of a few goofy teenagers, Mac Dre was interested in conveying the culture, the entire experience.

His music made it seem like life was a party—albeit one with a very real and dangerous underbelly, and he was the spiritual center of the entire movement, a pill-popping community elder who was as much a force of nature as a rapper. When he was murdered in 2004, he left behind a musical legacy that remains largely underappreciated-albums like Genie of the Lamp, Al Boo Boo and Ronald Dregan, despite their whimsical titles and album art, are impeccable projects that show the true strength of Mac Dre's sound-a sound that's still influential on records like Drake's "The Motto."

5. Kool Keith

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From: Bronx, NY
Signature Song: Ultramagnetic MCs "Kool Keith Housing Things" (1988)

Kool Keith is an interesting case; in the wake of his 1996 album with Dan the Automator, Dr. Octagonecologyst, the rapper became something of a critical favorite. The combination of his disregard for hip-hop conventions, his lyrical eccentricities (see song titles like "Halfsharkalligatorhalfman"), sci-fi obsession ("Earth People") and general prurience ("Girl Let Me Touch You") were the perfect critic's cocktail. The record was a solid one, but the Kool Keith obsession in certain circles was a bit over the top, raising questions about whether that appreciation might be a bit condescending.

There's no denying the fact that Keith remains an incredibly distinctive, clever rapper, one who has long evaded the boxes the industry might try to stick him in. He got his start with the still-underrated Ultramagnetic MCs, arising during one of hip-hop's headiest years, 1988. Going up against a series of indisputable classics, the group's enormously creative debut slipped under the radar of many, but the record's enduring influence helped create a lane for rappers who weren't afraid to be the oddball in the room.

4. Tragedy Khadafi

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From: Queens, NY
Signature Song: Tragedy Khadafi "Arrest the President" (1990)

Queensbridge-based Tragedy Khadafi has been in the industry since the mid-1980s, and has collaborated with many artists who found considerably more mainstream success and/or critical respect. Hamstrung by bad luck and perpetual recidivism issues, Tragedy still receives attention from fans of Queensbridge hip-hop and European record collectors, but otherwise doesn't get the props showered on many of his peers.

He debuted on 1985's Super Kids single "Go, Queensbridge" with DJ Hot Day; this drew the attention of Juice Crew producer Marley Marl, who made the rapper (then known as MC Percy) a 'junior member' of the crew in 1987. After a robbery conviction sent him to the sidelines, he returned with a new name and a newfound interest in Five Percenter ideology. Calling himself the Intelligent Hoodlum, he released a self-titled album (produced by Marley Marl and Large Professor) that was full of energized, politically excoriating hip-hop that captured the sound of a more conscientious era. "Arrest The President" was a clear standout.

His second and final LP as Intelligent Hoodlum, Tragedy: Saga of a Hoodlum, found the rapper reaching for a more diverse, modern sound, thanks in part to production from underrated beatmaker K-Def. Among the highlights were "Grand Groove," which re-incorporated the same sample as DJ Hot Day's "Hot Day Master Mix," (the Super Kids had appeared on the b-side back in 1987) and the "Grand Groove (Bonus Mix),", a powerful, elegiac reflection on mortality.

The rapper had evolved, becoming more reflective and worldly. But his explicit political consciousness passed once the artist started recording with Capone N Noreaga in the late 1990s. Although he's only credited as a guest artist throughout the record, the rapper was a driving force behind the group's seminal 1998 debut The War Report; Capone, who was incarcerated midway through the recording process, has less airtime on the record than the newly rechristened Tragedy Khadafi.

Khadafi appeared on eight tracks, and the record became a seminal event in the revitalization of New York gangster rap during the late 1990s. Khadafi continued to record after a falling out with Noreaga, first as a member of the Iron Sheiks alongside friend Imam T.H.U.G., then solo. His later records slid further from recognition, but tracks like 2003's "Neva Die Alone pt. 2" proved the rapper still has a striking gift for narrative that many of his contemporaries couldn't match.

3. The D.O.C.

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From: Dallas, TX
Signature Song: The D.O.C. "It's Funky Enough" (1989)

Younger rap fans mostly know The D.O.C. from various shout-outs other rappers have given him over the years, like Jay-Z saying, "No one can do it better." But old-school rap heads know the The D.O.C. as one of the greatest wordsmiths of the '80s, on par with legends like Kool G Rap, Big Daddy Kane, and Rakim. His legacy lies in his aforementioned debut album, No One Can Do It Better, which featured the classic opening track "Funky Enough."

Sadly, The D.O.C.'s promising career came to a halt when he was involved in a car crash that damaged his larynx and basically ruined his voice-a rapper's only instrument. He has tried releasing albums since then but he simply wasn't the same. But that doesn't mean he didn't find ways to influence the game. DOC certainly ghostwrote many verses during both the N.W.A., Death Row, and Aftermath eras of Dre's career because even if he didn't sound the same, his pen game was as sharp as ever.

2. Big Pun

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From: Bronx, NY
Signature Song: Big Pun f/ Joe "Still Not A Player" (1998)

We already hear the shouts of disbelief: "Are you guys crazy? How can one of the most respected lyricists ever be slept-on? This is Complex's WORST LIST EVER." Aww shucks, thanks guys—we try. Anybody who knows anything about rap knows Punisher was one of the best to ever do it. Rap nerds quote his tongue-twisting rhymes like Bible verses. Yet he's still underrated because he's an A1 rapper who often gets second-class status because he didn't get to make many albums before his untimely death.

We're not saying Pun isn't acknowledged; we're saying that his influence has waned as the years have passed. True, he only got to drop two albums, but then again so did Biggie and Big L-and they're regularly touted in GOAT conversations. Compare Pun's influence to someone like DMX who was on fire in '98 and '99 and basically flamed out afterward. Pun still doesn't get enough credit for his humor, his rhyme style, and the way he effortlessly worked Spanish into his rhymes. Years after his tragic passing, the Dreamshatterer's rhymes still baffle our skulls.

1. Tech N9ne

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From: Kansas City, MO
Signature Song: Tech N9ne "Imma Tell" (2002)

Tech N9ne is the most underrated rapper ever but thanks to his incredibly loyal fanbase, he's also one of the most successful independent rappers ever. Tech was certainly ahead of his time when it came to business. He found ways to win independently throughout the 2000s when most rappers were going on SMACK DVD to show off how much advance money they got from their major deal. He built his Strange Music label from the ground up on the foundation of his top-notch rapping.

We'll never understand why hip-hop heads front on Tech. He's a rapper's rapper, a first-rate lyricist capable of a variety of styles who can spit double-time with the best of them. Plus, he puts on one of the best live shows in all of hip-hop (he was highly offended when the L.A. Times accused him of lip-syncing). In other words, he's the exact opposite of all the things bitter rap fans say is wrong with rap music today.

So how come he's so unappreciated? Well, some of it certainly has to do with region. Tech puts on for the Midwest, a part of the country many people dimiss as the "flyover states." Plus, he's embraced movements most rap fans refuse to acknowledge, like the Juggalos. And ultimately, no matter how you look at it, Tech is a hardcore rapper who's always said that he'd never go mainstream, the mainstream would come to him.

Last year it really did when Wayne gave him a chance to shine on Tha Carter IV (of course he killed his verse) and he even scored a Billboard hit with his album, All 6s and 7s. Bottom line: in 2012, he landed at number 20 on Forbes annual list of Hip-Hop Cash Kings. But he was winning even before then. In 2008, the three rappers who made the most money from touring were Jay-Z, Kanye West, and...guess who?

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