The 50 Greatest Chicago Rap Songs

#50. Kanye West f/ Chris Martin "Homecoming"

Say what you want about the Yungin's personal life, but the kid makes hits—period. Berg seemingly came out of nowhere when this dropped in 2007, but the truth is the artist formerly known as Iceberg had been lurking around the industry for years. He was first signed to Chicago's Infared Music (the indie label that now houses L.E.P. Bogus Boys) and later joined forces with DMX's now-defunct Bloodline Records. Whatever they taught him worked, as "Sexy Lady" reached No. 18 on the Billboard Hot 100.

Wait, No I.D. was once a rapper? And had an album out? Well, if you just began listening to hip-hop in the 21st century, you might have missed the rapping debut of Kanye West's mentor. In 1997, Relativity Records was doing a dual push for their two Chicago blue chips, Common and No I.D. If you remember correctly, Accept Your Own & Be Yourself (The Black Album) and One Day It'll All Make Sense (a.k.a. two of the longest album titles of all time—of all time!) dropped within weeks of each other. With producer/MC Dug Infinite playing Ghostface to No I.D.'s Raekwon, these two went on to record almost every track together, with "The Real Weight" being one of the album's obvious standouts.

In 1996, Grav dropped Down to Earth via independent label Correct Records. The album may be long forgotten by casual hip-hop fans, but those who know recognize this as the first-ever project largely produced by a then-teenage Kanye West. "City to City," which featured AWOL Beatnut Al Tariq, was the B-side to Grav's single "Sex," another dope track produced by a young 'Ye.

Like it or not, one thing the Windy City is best known for is its gang culture. Here, DA Smart literally walks listeners through the city, breaking down each organization and the side of town and neighborhood they represent. Straighten up your hat and take a walk with DA.

Cap D and Tone B. Nimble formed the group All Natural in high school (both aspiring DJs, they owned one turntable each), and in 1996 they released their first 12-inch, "50 Years," after saving up enough money to press it up themselves. Inspired by the KRS-One line "50 years down the line you can start this, 'cause we'll be them old school artists," Cap and Tone boasted that years from now we'd still be rocking to this tune. Guess they were right, as this joint is a certified Chicago classic. So classic, in fact, that Chicago filmmaker/director Konee Rok made a short film dedicated to the song. Here's to 50 more...

Fresh off their success on Rash's comeback album, Be, 'Ye and Com joined forces again for "Southside," a dedication to the side of town south of the Loop. Com sounded reinvigorated, spitting, "The broads, the cars, the Half Moons, the Stars/I'm like Jeff Fort the way I get behind bars." Filled with Chi-Town lit, "Southside" included shout-outs and name-drops to many of the Chi's finest, including PsychoDrama and Crucial Conflict, who, ironically, are from the Westside.

If this is your first time hearing this, you are about to experience something so cold, man. Before Jay-Z's Blueprint dropped, cementing Kanye West as an A-list producer, 'Ye was still working with lesser-known artists around Chicago, trying to help get their careers off the ground. One artist in particular was Payroll, a street-oriented artist from the notorious Humboldt Park neighborhood of Chicago. Pay purchased a stellar Kanye-produced track and crafted "Never Change"—an ode to struggle and strife on the mean streets of Chicago. Somehow this track ended up in the hands of Jay-Z, who was smitten with the beat and chorus, and he decided he wanted to keep it for himself. So Pay's "Never Change" became Jay's "Never Change" and appeared on the classic album The Blueprint. Supposedly, Payroll was broken off nicely for his services, but as hood legends go, he wasn't happy with the overall settlement. What ensued after would become known as the "bottle incident," in which Payroll allegedly showed up to a birthday party Kanye and the Go-Getters were chilling at, brandishing a champagne bottle. In the aftermath, well, GLC earned himself a new nickname—"the Knockout King." Hey, it's hearsay! Not saying he's referring to this particular incident, but on "Southside" Kanye does rhyme, "I ain't gotta say it, man, dog, trust me/Bust somebody head, GLC, where was we?"

If you didn't have Rap City or The Box back in the mid-'90s, there's a good chance you missed this A-plus collaboration from Just Ro and Common. With Just Ro playing the hustler and Common playing the scholar, the pair traded Chi-centric bars over Just Ro's rugged production—with Common kicking two of his most inspired guest verses ever. This was post-Resurrection and pre–One Day Common, when Rash was arguably at his sharpest. The track can be found on Just Ro's super-indie EP Make It Happen.

Although producer Double O is from Brooklyn, many consider Kidz in the Hall to be a Chicago group (probably to the dismay of Double O—ha!), as their frontman, Naledge, hails from the Southside of the Chi. After leaving Rawkus for Duck Down in '07, the duo rose to prominence after this Masta Ace–assisted single (Ace actually re-recorded his line from "Born to Roll" so Kidz wouldn't have to pay for the sample) caught on like wildfire. The record came at the right time, as this hard-hitting throwback track was the sound that was popping in Chicago. What else could a brother to do other than support this?

Believe it or not, back in the mid-'90s, Da Brat was one of the biggest artists in hip-hop. First female rapper to go platinum? Check. The go-to female featured artist of that era? Check. So it was only right that she'd collaborate with the King of New York. That was a rite of passage, after all. This Jermaine Dupri–produced, Gap Band–sampling banger was the standout cut on an otherwise boring Bad Boys soundtrack.

Prior to Kanye shocking the world with The College Dropout, he was still trying to prove to the industry that he was viable as a rapper. In late '02 and early '03, Kanye began releasing a slew of mixtapes featuring not only tracks he'd produced for other artists, but also the solo material he'd been perfecting for years. Perhaps the best of these mixtapes was Get Well Soon, which featured early versions of "Through the Wire," "Jesus Walks," and perhaps the best of his early work, "My Way." "My Way" featured Yeezy's signature chipmunk soul sample, and darts aimed at the inhabitants of the City of Hella Haters. At the time, he was almost on: "Y'all just talk about my dough/How I left Chicago/How I'm the only one eatin'/Shut ya pie hole."

Rashawnna Guy and Lateefa Harland were only teenagers when they were handpicked by No I.D. to appear on his Relativity Records debut, Accept Your Own & Be Yourself (The Black Album). They later joined the same label and released their debut album, Change the Game, in 1999. Although the duo didn't quite follow through on their album title's promise, they did go on to drop "Here I Go"—their No I.D.–produced single—which reached No. 9 on the Hot Rap Singles chart and got burn on BET, MTV, and The Box. Shortly thereafter, Rashawnna dropped the Ra and went on to join Ludacris' DTP imprint for solo endeavors, while Lateefa dropped the La and became one of Chicago's top radio personalities. Talks of a reunion have been rumored for years, but they've never come to fruition.

In 2007, Kanye West's former protégé GLC was able to stand out on the crowded G.O.O.D. Music–sponsored Can't Tell Me Nothing mixtape with "I Ain't Even On Yet"—a track for those who assumed GLC was "on" (read: rich, famous, and signed) due to his big name affiliations. Three years later, GLC is well on his way to being on after inking a deal with EMI and releasing his debut album, Love, Life & Loyalty this past fall.

If you hadn't noticed, there's a movement currently brewing in Chicago. Who is this duo every DJ and Internet tastemaker is talking about? Well, they're the Low End Professionals, repping the "low end" of the Southside. After putting in work for years in Chicago's streets (and the underground rap scene), Count and Moonie burst into the spotlight after their breakout hit, "Chicago Niggaz," debuted on Shade 45 and the video landed in rotation on MTV Jams. This gritty record showed the world how we do things in this cold city. What was once a secret is now turning into a national phenomenon, with the Bogus Boys (named after the infamous Larry Hoover hit squad) getting love across the board.

In 1996, the underground trio from the Westside (consisting of Yung Buk, Newsense, and Psyde) reemerged with "Do What You Wanna Do," a haunting, Legendary Traxster–produced monster dedicated to tough talkers, with explicit warnings for their foes. This single moved so many units independently that it piqued the interest of Rap-A-Lot and Suave House Records, and eventually lead to a record deal with the House Tony Draper Built. Although their Suave House debut, Time Vs. Life, never saw the light of day, PD remains one of the most heralded acts in the Chicago hip-hop history—till the world blows up.

The North Pole's Ill State Assassin was one of the Chi's first hip-hop acts to get exposure on a national level, all while staying independent—and being white. E.C.'s 1995 opus, Illa LP, showcased traditional boom-bap rap with a Chicago twist. The video for "On Ill," which was a mainstay on BET's Rap City and The Box, exposed the world to Chicago's underground hip-hop scene, featuring local graf writers, B-boys, and MCs getting busy. This self-produced track is a testament to why E.C. should be held as a pioneer of Chicago hip-hop.

For years there's been disputes regarding who invented the rapid-fire, high-speed Midwest flow in hip-hop. Was it Bone Thugs-N-Harmony out of Cleveland? Or was it the various acts representing the Westside of Chicago (Do or Die, Twista, and Crucial Conflict)? Hell, even Three 6 Mafia staked a claim that it began in Memphis. Things escalated between Chicago and Cleveland when Bone took a shot at Twista on their 1997 single, "Look Into My Eyes," labeling T as a style biter. Not one to back down from a battle, Twista (alongside his protégés the Speedknot Mobstaz) returned fire with "Crook County (Bone Crusher)," an all-out assault on "Hoes-N-Harmony." On this scathing diss, the Mobstaz threatened that Bone would be "seeing Eazy E soon" and claimed that Krayzie played fanboy when the groups crossed paths in New Orleans. The beef was squashed a short while later and both factions went on to record a handful of songs together. But rumors and stories still swirl to this day that Bone had to sneak in and out of Chicago with heightened security during this heated time period.

After Common was featured in The Source's "Unsigned Hype" column, Relativity Records quickly snatched up the budding Chicago talent and released his debut album, Can I Borrow a Dollar? Over production from childhood friends Immenslope (later known as No ID) and Twilite Tone, Com's early style was much more sing-songy and (ahem) "high-pitched" than what we hear nowadays. This joint in particular was a fun record, chock-full of punchlines and pop-culture references.

After striking gold with their debut album, The Final Tic, the 'Flict were in high demand throughout the industry. Seriously. From 1997 to 2000, they appeared on just about every single hip-hop-related motion-picture soundtrack and were the go-to guests if you wanted that Midwest appeal on your record. Group member and producer Wildstyle helped craft the Midwest bounce that was popular at the time (the man does NOT get his proper credit), and he took it to another level with the foursome's contribution to 1997's Rhyme & Reason soundtrack, "Bogus Mayn" (which was also a popular slogan in the city). The bouncy track with a country twang introduced listeners to what being a bogus human being entails: women, guns, pimping, and partying. Sometimes you just can't help but to be bogus.

Going to the well one too many times? Nah, not for this follow-up to the gold-selling smash "Po Pimp." The gang was all there for the second edition, which featured Do or Die, Twista, Johnny P, and Traxster playing their reoccurring roles. Usually these type of follow-up songs fail miserably ("Make Em Say Uhh #2," anyone?), but "Still Po Pimpin" was able to recapture the magic of the first and create a dope record that stands at the top of Do or Die's catalog.

Before racking up platinum plaques for producing for the likes of Twista, Ludacris, Mariah Carey, and Do or Die, the Legendary Traxster fronted the street-hop duo Dedicated 2 Tha Streets. Along with co-star K-Tone, he recorded some of the earliest "street music" in Chicago history and stayed true to the name the group claimed. In 1994, the Ill State duo released their 12-inch for "Doomsday," which also included the notable Toxic-featuring B-side "Dissin' These Fools," which took shots at Naughty By Nature, who was in a full-fledged battle with Twista at the time. D 2 Tha S never released a proper album, but did drop a few singles over the years. On a sad note, group member Trevor "K-Tone" Caston passed away on September 12, 2010, from complications from asthma. He will no doubt live on through his music. May he Rest In Power.

In 2007, there was an industry renaissance in Chicago with the birth of what critics dubbed "hipster-hop." However, drop that name in front of a so-called hipster-hop artist and you might end up with five fingers across the face. Artists like Kid Sister, Hollywood Holt, Million $ Mano, and Flosstradamus were packing venues and parties across the city, and it seemed like the media and labels were treating this movement as the next big thing in music. At the forefront of this phenomenon were Chuck Inglish and Mikey Rocks, otherwise known as the Cool Kids. This duo rose to prominence due to their colorful, throwback style of dress and hard-hitting, drum heavy, minimalist-style of production reminiscent of late '80s hip-hop. They caught national attention with their first single "Black Mags," which lead to Chuck and Mike starring in a Rhapsody commercial alongside Sara Bareilles promoting the track. The song, dedicated to their preference for pedaling a bicycle over pushing a skateboard (which was also very popular in Chicago at the time), cemented the two as the Chi's leaders of the new school.

After the guy with the "peach-fuzz buzz" made headlines with his scene-stealing verse on Kanye West's "Touch the Sky" and had the world wondering who this Fiasco character from Chicago was, Lupe hit the mixtape circuit hard, showcasing his way-over-your-head lyrics and intricate rhyme patterns. The Nottz-produced "Failure" is arguably Lu's greatest verbal display and still has listeners rewinding lines half a decade later. Watch out for those pennies from heaven when walking below the Sears Willis Tower.

Twista's 1997 opus, Adrenaline Rush, is a certified classic. It was huge regionally and eventually caught fire nationally, going gold with little to no major promotion or airplay. Pairing the Legendary Traxster's dark production with the Guinness Book of World Records–holding MC's rapid-fire delivery proved to be a winning formula, and there's no better example of this chemistry than "Overdose." This four-minute-plus verbal exercise proved that Twista could not only rap fast, but was also one of the best and most precise lyricists doing it. There have been rumors of a sequel (as Twista was abruptly cut off mid-flow on the original) for years, but it has yet to surface.

The daughter of blues legend Buddy Guy was anointed the first lady of Ludacris' Disturbing Tha Peace clique and released her debut, Worth Tha Weight, in 2004. After that project failed to set the world on fire, she had to come back strong and did just that with "Gettin' Some." Building the song around the infamous line from Too $hort's "Blowjob Betty," the ode to oral took the radio by storm (despite its raunchy content), cracking the top five on both the R&B and rap charts. The single later went on to sell a million copies, giving Shawnna her first platinum plaque as a solo artist.

Probably best known outside of Chicago for defeating the biggest rapper on the globe, Eminem, at Scribble Jam in the late '90s, Juice is a strong contender for the greatest freestyle rapper of all time. A mainstay on Sway & King Tech's "The Wake Up Show," Juice has embarrassed a laundry list of A-list, aspiring, and would-be battle MCs over the years. In 1997, storied Chicago production trio the Molemen (PNS, Panik, and Memo) released their Below the Ground EP, which contained Juice's underground hit "Freestyle or Written." The track, which featured one written verse and one freestyled verse, showcased Juice's pen game as well as his off-the-dome skills. The question is, can you tell which one is which?

After the success of Kanye's The College Dropout and Twista's Kamikaze in 2004, every A&R and label head was looking towards Chicago for the next big thing. The name ringing in the streets? Bump J—the new kid on the block whose Goon Squad mixtape series had the streets going bonkers. Execs from both coasts were wooing the MC to join their stable, but it was Lyor Cohen who eventually snagged the budding Goon after personally tracking him down in the streets and making him an offer he couldn't refuse. Touted as the "biggest deal since 50 Cent" (money-wise), Bump was quickly made a top priority at Atlantic and began work on his debut album, Nothing to Lose, which featured assistance from the likes of Kanye West, Rick James, Keyshia Cole, Boogz, and John Legend. "Creative differences" with the label kept Bump's debut from ever hitting shelves, and in 2007 he was granted a release from the label. Finding himself back at square one, Bump aligned with super-producer No I.D. and broke ground on a new project. Unfortunately, Bump's plans for stardom were derailed in late 2008, as he was pinched on federal bank-robbery charges. It was rumored that he was just days away from inking a deal with G.O.O.D. Music prior to his arrest. "Move Around," produced by Yeezy, was probably Bump's biggest record radio- and acclaim-wise, and was even used for a McDonald's commercial during the height of his buzz. Free Bump J!

The name Mikkey Halsted may be new to some, but those in the know recognize Mikk as one of the most storied MCs in Chicago history. After being discovered by Kanye West, Mikk was snatched up by Cash Money during their (first) heydey. After years of penning tracks for CMR and helping Lil Wayne "get on his shit," Mikk was tired of sitting on the shelf and departed for greener pastures over at Virgin during Jermaine Dupri's tenure. During this time, Mikk was hard at work with No I.D. (who was serving as executive producer) on his debut album, and out of this came "Liquor Store," which, surprisingly, was going to be Mikk's first single. The controversial record took liquor and corner stores in low-income areas to task for selling junk food and unhealthy products at inflated rates to those who didn't know or couldn't afford better. Chicago's Arab community in particular was grossly offended by "Liquor Store," and a handful of stores (from liquor to clothing stores) issued a full-on boycott of Mikkey Halsted's music and mixtapes. The Chicago Reader and NPR went on to do a feature on the track, which led to the Inner City Muslim Action Network launching an investigation into small Southside stores and "food deserts"—neighborhoods with poor access to healthy food. Now that's powerful music.

During the mid-'90s tensions were high between East Coast and West Coast artists, so it was safe to assume that artists from the Middle of the Map were exempt from such beef, right? Wrong. Taking offense to Common's allegory on "I Used To Love H.E.R.," which included the line "I wasn't salty she was with them Boyz N the Hood," Ice Cube called out names and flat-out dissed Common for the possible subliminal on Mack 10's "Westside Slaughterhouse": "All you suckas wanna diss the Pacific, but you busta niggas never get specific/Used to love H.E.R., mad ’cause we fucked her/Pussy-whipped bitch, with no Common Sense." Shots fired, indeed. Possibly taking Com Sense for a soft, tree-hugging backpacker, O'Shea was unaware that he'd "backed into a Four Corner Hustler" and probably didn't expect Chi-Town's Nas to come back as viciously as he did. Com went at Cube, labeling the Don Mega as a washed-up gangsta rapper who hadn't made a good album in years. The beef was later squashed after Cube and Common had a sit-down with Minister Louis Farrakhan, and in 2010 these rappers-ternt-actors are planning on starring in movies together.

Fans who were used to hearing E.C. Illa kick traditional hip-hop rhymes may have been taken aback by this ode to Chicago street gangs, but on the other hand, some dudes are People and some dudes are Folks. Instead of glorifying gang culture, E.C. served as a street professor, chronicling how the gangs spread throughout the city and giving listeners a firsthand account of how it affected him and his peers. He even recruited gang members from across the city to shout out their various organizations at the end of the song.

Although "Sky's the Limit" was the lead single and video from No I.D.'s debut (and only) album, Accept Your Own & Be Yourself (The Black Album), the project is probably best known for the track "State to State," featuring Common and Dug Infinite. This song is a testament to the chemistry that No I.D. and Common shared while working together during the early parts of their careers—the whole is greater than the sum of its parts. In 2010, Common and No I.D. reunited for the first time in 12 years for a Gatorade-sponsored track with Lupe Fiasco and Jennifer Hudson. Common has hinted that No I.D. will be handling some production on his upcoming album, The Believer, but only time will tell if that chemistry is still there. And can someone please find Dug Inf?

"Cold Hard, Never, Wild, Kilo finna bring it on, giddy up..." You thought Cru Con could only make records about pimpin' and gangbangin'? Well, think again. "Rodeo," the 'Flict's feel-good party-starter, was the perfect follow-up to their debut smash hit "Hay," which thrusted them into the public spotlight. This fearless foursome from the wild, wild Westside of Chicago, who were discovered by Fab 5 Freddy, may have been typecast as cowboys, but best believe there was nothing country about them.

After Twista came back for the first time by stealing the show on Do or Die's "Po Pimp," all eyes were on the fastest spitter in the Midwest to see what he was going to do next. No stranger to the industry, Tung Twista dropped his first album in 1992—the first-ever release on Loud Records. It was largely seen as a fast-rapping novelty record. Dropping the Tung from his title, Twista returned to the industry in '96 as a new man with a new sound. After the success of his pairing with producer the Legendary Traxster on "Po Pimp," Twist and Trax got back in the lab to try their hand at another record. The result was "Emotions," a song that caught fire instantaneously in the Chicagoland area. Released independently on Creators Way Associated Labels (CWAL—the label owned by Traxster, Kevin Brinson, and Leroy Burton), the Johnny P–assisted "Emotions" instigated a major-label bidding war for Twista that ended with CWAL landing a partnership with Atlantic Records.

Riding the wave of "Po Pimp," AK, Belo, and Nard, better known as Do or Die, struck platinum with their debut, Picture This. Considered a classic by many, Picture This was structured around the the sound that Do or Die and the Legendary Traxster created alongside supporting cast members Twista and Johnny P. "Playa Like Me & You" ushered outsiders in to the lavish lifestyles D.O.D. and other true players were living on the west side of town. Throw on your Dobbs hat, put on your best suit, and smoke and ride with a playa. Free Belo!

After Lupe Fiasco's debut Food & Liquor suffered the "leak heard 'round the world" in 2006, leading to less-than-stellar album sales, the man born Wasalu Jaco had to come back in a major way. He did just that with "Superstar," the first single off his second album, The Cool. Laughing in the face of the sophomore slump, this Matthew Santos–assisted smash helped Lu attain superstar (get it?) status and pushed The Cool to gold status. The single peaked at No. 10 on the Billboard Hot 100 and ushered Fresh Cool Young Lu into hip-hop's A-list category.

After Common's fifth album, Electric Circus, was seen as a flop, failure, and letdown in the eyes of die-hard fans (the album wasn't that bad in hindsight), hip-hop had written off Com as a tragic victim of Baduizm. It also didn't help that he was dressing like a boho hobo and proposing to deaf women via cue cards in his music videos. How do you resurrect your career after such public scrutiny and backlash? Well, you show up on The College Dropout and murder everyone on their own shit, that's how. After the reaction to Kanye and Common's pairing on "Get 'Em High," it was only right that Yeezy bring Common into the G.O.O.D. Music fold to help get his rap career back on track. Bringing it back to his b-boy roots, Common returned to Chicago to craft Be (an acronym for "Basement Elevation"), arguably the most important album of his career. Winning over critics, fans, message boards, and the streets, "The Corner" was the perfect reintroduction for those who'd written off Rash as a granola-eating weirdo.

If it wasn't for Da Brat-tat-tat-tat proclaiming she was "coming straight from the 6-0-6-4-4," most would've confused her for another one of Jermaine Dupri's ATLien proteges. After winning a Yo! MTV Raps–sponsored talent show, the woman born Shawntee Harris cashed in her grand prize, which was getting to meet the then-hot duo Kriss Kross. So impressed were they with Da Brat's talents, that Chris and, well, Chris, introduced her to their boss Jermaine Dupri, who then offered her a contract with So So Def. Despite her being labeled as a budget female version of Snoop Doggy Dogg, Da Brat's debut album, Funkdafied, propelled by the title-track single, debuted at No. 1 on the Billboard rap charts and allowed her to become the first platinum-selling female rapper ever. Free Da Brat!

While "Po Pimp" is the most celebrated Chicago pimp anthem of all time, "Magic" is the O.G. This smooth, slow, and crawling dedication to the possessing power of the P ranks as Traxster's first hit ever, and was the world's first introduction to the most known unknown rap group from Chicago. "Magic" was released as a cassette single that featured two other tracks and the radio version, via the super-indie Uncle Rick Records. The single circulated throughout mom-and-pop stores in Chicago and eventually spread throughout the Midwest and South. Although PD never achieved megastar status, this song alone ensures their entry into the record books.