The 50 Greatest Chicago Rap Songs

From Kanye hits to underground bangers, here are the Windy City's all-time best.

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Complex Original

Image via Complex Original

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In 2010, Andrew Barber of Fake Shore Drive joined forces with Complex to drop a list of the best hip-hop songs in Chicago rap history. Then, Chicago hip-hop exploded, with one of the most commercially successful periods in its history. Many young artists were signed and gained national attention. We've adjusted the list to account for Chicago's recent changes, and adapted Andrew's list to account for the impact of a new generation. 

Chicago. The Windy City. The Second City. The City of Hella Haters. Call it what you want, just don't call it a city that hasn't contributed to hip-hop's legacy. Often dismissed as a town buried within "flyover states" and a place where people only listen to house music, Chicago has a rich hip-hop history that dates back to the early '90s, when its two most prominent artists—Common and Twista—landed deals and released their debut albums.

Representing different sounds and different sides of town, these two kicked down the doors and ushered in a whole slew of innovative and unique artists who were making music differently than their counterparts on the coasts.

From the wild styles of Crucial Conflict to the laid-back, pimptastic sounds of Do or Die, Chicago was breaking through with slang and swagger unseen in other regions of the U.S. Years later, a boisterous up-and-coming producer would emerge as arguably the greatest and most polarizing rap artist of all time and change music completely. The City of Broad Shoulders, indeed.

Now, we easily could've made this list based on Kanye, Twista, Common, and Lupe records alone, but there's more to Chicago's story than just these four juggernauts. In the immortal words of No I.D., "the one that's in the middle is the one that sees the most." So come visit the Middle of the Map and take a ride down Fake Shore Drive for The 50 Greatest Chicago Rap Songs.

Written by Andrew Barber (@FakeShoreDrive), Alexander Gleckman (@andfeedingyou), David Drake (@somanyshrimp), Edwin Ortiz (@iTunesEra) and Rob Kenner (@Boomshots)

RELATED: The 100 Best Kanye West Songs
 

50. Kanye West f/ Chris Martin "Homecoming" (2007)

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Producer: Kanye West
Album: Graduation
Label: Roc-A-Fella, Def Jam


If you were on the Kanye train (ayo?) early on, then you heard the first incarnation of "Homecoming" on the Get Well Soon mixtape. The O.G. version of "Home" featured a then-unknown John Legend (er, Stephens at the time) and a completely different beat altogether. The extended metaphor for Yeezy's hometown centers around "Wendy" (as in Windy City-get it?) and captures Kanye's bittersweet relationship with the place he calls home.

Five years later he recruited Chris Martin of Coldplay to re-record the song during a jam session at Abbey Road Studios in the U.K. "Homecoming" was finally properly released in 2007 on Kanye's third album, Graduation. The incredibly dope Hype Williams–directed video features shots of various landmarks in Chicago (Millennium Park, the Cabrini Green projects, Sears Tower), as well other hip-hop artists (Common, L.E.P. Bogus Boys).—Andrew Barber

49. Yung Berg f/ Junior "Sexy Lady" (2007)

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Producer: Rob Holladay
Album: Almost Famous: The Sexy Lady EP
Label: Koch, Epic


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.—Andrew Barber

48. D.A. Smart "Walk Wit Me" (1997)

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Producer: The Legendary Traxster
Album: N/A
Label: N/A


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.—Andrew Barber

47. King Louie "Val Venis" (2012)

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Producer: C-Sick
Album: N/A
Label: Epic

King Louie was the man, little did you know—or maybe you ain't even know at all. But once the "Val Venis" came out, there was no contesting Louie's mass appeal, as corroborated by his extensive and consistent back catalog. Louie had first released a clip of himself "wildin'" (while "Vallin'" of course) to the beat of what would later become his monstrous "Val Venis" single, in which our dude dances hilariously to the C-Sick instrumental, announcing: "Hello ladies."

But it became clear when the actual song came out that it was no longer a joke, and that he went in on the track as he is wont to do. Louie is just so good at rapping that his armchair flow sounds as if he could have been in the middle of something else, (like waking up on Band Ave., taking a band bath, or telling jokes to his anthropomorphic bandz) and he just turned to you for a second to spit a few verses, every line of which rhymes with either the word "dough" or "MUBU." Or maybe it's really just that easy for him. For Louie, a chorus isn't even a necessary element to one of his songs, because it seems like the guy just has infinite bars, but here he simply had to declare his metaphysical resemblance to a Canadian wrestler to get his point across. Naturally. —Alexander Gleckman

46. All Natural "50 Years" (1997)

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Producer: Cap D
Album: No Additives, No Preservatives
Label: All Natural Inc.


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...—Andrew Barber

45. Da Brat f/ The Notorious B.I.G. & Jermaine Dupri "Da B Side" (1994)

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Producer: Jermaine Dupri
Album: Bad Boys Soundtrack
Label: So So Def, Columbia, Sony


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.—Andrew Barber

44. Kidz in the Hall "Drivin' Down the Block (Low End Theory)" (2008)

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43. MC Juice & Rhymefest "How We Chill 1 & 2" (1996)

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42. Infamous Syndicate "Here I Go" (1997)

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41. Triple Darkness "Chop Up That Paper" (2000)

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Producer:
Album: Cold Blooded
Label: Wicked Entertainment


Triple Darkness' rap style fit in well with fellow West Side rappers like Do or DIe or PsychoDrama; the trio of DaWreck, Hanius and Trick released the Cold Blooded EP in the late-1990s, and the slow, ethereal "Chop Up That Paper" was an immediate highlight. With slow-rolling production featuring a chopped vocal sample and eerie melodic backing, the group spit midwest double-time flows into the history books with a track that epitomized what made mid-late '90s Chicago such a distinctive sound.—David Drake

40. GLC "I Ain't Even On Yet" (2007)

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Producer: Xcel
Album: Can't Tell Me Nothing
Label: G.O.O.D. Music


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.—Andrew Barber

39. L.E.P. Bogus Boys "Chicago Niggaz" (2010)

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Producer: Black Metaphor
Album: Don't Feed Da Killaz Vol. 3
Label: Infared Music


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.—Andrew Barber

38. Lil Durk "L's Anthem" (2012)

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Producer: Paris Beuller
Album: I'm Still A Hitta
Label: O.T.F.

Representing Chicago's Englewood neighborhood, dreadlocked drill rapper Lil Durk parlayed a huge YouTube buzz into a deal with Def Jam. His music may be melodic but when Durk says he's a "hitta" you'd best believe he's about that life. The Ls in this song reportedly refer to Lamron, a Black Disciples gang set from 63rd & Normal Street. "Lamron," of course, is normal spelled backwards. Listening to Durk's music, one thing's for sure: nothing in Chicago is normal anymore. —Rob Kenner

37. Kanye West f/ DJ Khaled "Cold" (2012)

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Producer: Hit-Boy
Album: Cruel Summer
Label: G.O.O.D. Music, Def Jam


Originally titled "Theraflu," this Kanye West single came out of nowhere to set the Internets on fire. Dropping Anna Wintour's name and taunting PETA in the same breath, acknowledging his relationship with Kim Kardashian and needling her ex Kris Humphries, this song was packed with quotables for every occasion. ("Don't talk about style cause I'll embarrass you," anyone?) But what makes it a Chi-town anthem is Power 92 radio fixture DJ Pharris shouting out all those Windy City neighborhoods on the outro. Chicago stand up. —Rob Kenner

36. PsychoDrama "Do Whatcha Wanna Do" (1996)

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35. E.C. Illa "On Ill" (1995)

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34. Twista & The Speedknot Mobstaz f/ Newsense "Crook County (Bone Crusher)" (1998)

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Producer: The Legendary Traxster
Album: Mobstability
Label: Creator's Way, Atlantic


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.—Andrew Barber

33. Common Sense "Soul by the Pound" (1992)

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Producer: Immenslope (No I.D.)
Album: Can I Borrow a Dollar?
Label: Relativity


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.Andrew Barber

32. Chief Keef "Love Sosa" (2012)

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Producer: Young Chop
Album: Finally Rich
Label: Glory Boyz Entertainment, Interscope


This one crushed the dreams of all Sosa haters and tiptoe-danced (as in the video) on the remains. You would love Sosa, whether you liked that fact or not. For everyone who thought that Keef and Chop had peaked with "I Don't Like," the teenaged duo came back unfuckwittably with another one of the defining records of the year. It wasn't even what many would call rap, but like a lot of great rap, it tested the genre's boundaries. The cadence of the song might as well be that of a nursery rhyme, but the lyrical content would leave you slumped over.

The album version (perhaps since everyone, like Drake for example, had already listened to the song well over a hundred times) featured a truncated rant from a Chicago fan who for some reason was WorldStarrily passionate about the way Keef was being perceived among his peers. Complete with incontestable evidence like "you know he roll with Lil Reesie and them" to support his thesis that Keef was indeed of hitta nature, it became clear early on, as sure as the fact that Tadoe enjoys his molly water, that this song would slap you into an unrecoverable Sosa submission. —Alexander Gleckman

31. Do or Die f/ Twista & Johnny P "Still Po Pimpin'" (1998)

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Producer: The Legendary Traxster
Album: Headz or Tailz
Label: Rap-a-Lot, Virgin


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.—Andrew Barber

30. D 2 Tha S "Doomsday" (1994)

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29. The Cool Kids "Black Mags" (2007)

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Producer: Chuck Inglish
Album: The Bake Sale
Label: C.A.K.E., Chocolate Industries


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.—Andrew Barber

28. Lupe Fiasco "Failure" (2006)

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27. Twista "Overdose" (1997)

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Producer: The Legendary Traxster
Album: Adrenaline Rush
Label: Creator's Way, Big Beat, Atlantic


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.—Andrew Barber

26. Shawnna "Gettin' Some" (2006)

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Producer: Xcel
Album: Worth tha Weight
Label: Disturbing tha Peace, Def Jam


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.—Andrew Barber

25. Chance the Rapper "Juice" (2013)

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24. Molemen f/ Juice "Freestyle or Written" (1997)

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Producer: Molemen
Album: Below the Ground
Label: Molemen


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?—Andrew Barber

23. Bump J "Move Around" (2005)

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Producer: Kanye West
Album: Nothing To Lose
Label: Atlantic


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!—Andrew Barber

22. Mikkey Halsted "Liquor Store" (2007)

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Producer: 1120
Album: Chicago: The Photo Album
Label: N/A


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.—Andrew Barber

21. Common "The Bitch in Yoo" (1996)

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Producer: Pete Rock
Album: Relativity Urban Assault
Label: Relativity


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.—Andrew Barber

20. E.C. Illa "What You Be About" (1995)

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Producer: E.C. Illa
Album: E.C. Illa LP
Label: Wicked Entertainment


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.—Andrew Barber

19. Chief Keef f/ Lil Reese "I Don't Like" (2012)

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Producer: Young Chop
Album: Finally Rich
Label: Glory Boyz Entertainment, Interscope

Before Kanye got his hands on it, Chief Keef's breakout single was simplicity itself. Created by a couple of teenagers in a Chicago kitchen studio while Keef was on house arrest in the midst of Chicago's murder epidemic, "I Don't Like" seethes with pent-up emotion. The G.O.O.D. Music remix added lots of star power but lost some of that rawness, demonstrating the power of the original and proving the old adage that less is more. —Rob Kenner

18. No I.D. f/ Common & Dug Infinite "State to State" (1997)

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17. Crucial Conflict f/ Toi "Ride the Rodeo" (1996)

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Producer: Wildstyle
Album: The Final Tic
Label: Pallas, Universal


"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.—Andrew Barber

16. Twista f/ Johnny P "Emotions" (1997)

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Producer: The Legendary Traxster
Album: Adrenaline Rush
Label: Creator's Way, Big Beat, Atlantic


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.—Andrew Barber

15. Do or Die f/ Johnny P "Playa Like Me & You" (1996)

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Producer: The Legendary Traxster
Album: Picture This
Label: Rap-a-Lot, Virgin


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!—Andrew Barber

14. Lupe Fiasco f/ Matthew Santos "Superstar" (2007)

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Producer: Soundtrakk
Album: Lupe Fiasco's The Cool
Label: 1st & 15th, Atlantic


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.—Andrew Barber

13. Common f/ Kanye West & The Last Poets "The Corner" (2005)

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Producer: Kanye West
Album: Be
Label: G.O.O.D. Music, Geffen


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.—Andrew Barber

12. Da Brat "Funkdafied" (1994)

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Producer: Jermaine Dupri
Album: Funkdafied
Label: So So Def


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!—Andrew Barber

11. PsychoDrama "Magic" (1994)

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10. Kanye West "Through the Wire" (2003)

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Producer: Kanye West
Album: The College Dropout
Label: Roc-A-Fella, Def Jam


After it was announced that the guy who did all of those great beats on The Blueprinthad just inked a solo record deal with Roc-A-Fella, most assumed the only place they'd actually see the album was in "coming soon" advertisements on liner-note inserts in the latest Jay-Z release.

You know, right there beside Oschino & Sparks and Rell. Taking his destiny into his own hands, Kanye went into his own pockets to finance the video for "Through the Wire" (directed by then-unknown duo Coodie & Chike), which he serviced to television and radio himself.

The unexpected hit, recorded just two weeks after West almost lost his life in a gruesome car accident, featured him literally rapping through the wire, as his jaw was wired shut. The world had no idea what they were in for.—Andrew Barber

9. Common "Resurrection" (1994)

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Producer: No I.D.
Album: Resurrection
Label: Relativity


Everything about Common's second single from the album of the same name screams Chicago. From the feeling to the samples to the references-this is the song made for cold February nights along Lake Michigan. This is the sound that the Bony Homey from Stony and No I.D. were born to create.

Bonus: Stepping out of his Chicago comfort zone, Common recruited Large Professor (who could do no wrong at the time) for the equally dope and important remix.—Andrew Barber

8. Twista f/ Kanye West & Jamie Foxx "Slow Jamz" (2003)

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Producer: Kanye West
Album: Kamikaze
Label: Atlantic


Life is a funny thing. What began as just an album interlude featuring Jamie Foxx doing a stand-up comedy bit turned into the biggest hit of Twista's career and was the catalyst for Chicago hip-hop's come-up in the mid-aughts. "Slow Jamz" almost didn't happen for a number of reasons (lost hard drives containing verses, missed deadlines, etc.), but when it hit, it hit hard.

Twista, who'd been in label limbo at Atlantic and hadn't released an album in seven years, officially came back for the third time with this No. 1 single (it was actually the first No. 1 single for all three artists), which pushed Kamikaze to double-platinum status.—Andrew Barber

7. Kanye West "Can't Tell Me Nothing" (2007)

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Producer: Kanye West, DJ Toomp
Album: Graduation
Label: Roc-A-Fella, Def Jam


If there were one song to describe Kanye West and his career, this would be it. A statement, a promise, and a motto, "Can't Tell Me Nothing" set the tone for his defiant third album, Graduation, and gave West his first-ever street anthem.

Attaining the almost impossible, this track resonated with hip-hop purists, college dropouts, and trap stars. Recruiting the red-hot DJ Toomp to co-produce the track and inviting Jeezy to add his patented ad-libs was the icing on the cake. This was the exact moment in West's career when he went from rapper to international superstar.—Andrew Barber

6. Lupe Fiasco "Kick, Push" (2006)

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Producer: Soundtrakk
Album: Lupe Fiasco's Food & Liquor
Label: 1st & 15th, Atlantic


After Lu's big debut on Kanye West's "Touch the Sky", the general public wasn't sure what to expect from the new kid from Chicago, but they patiently awaited his first single. When it finally sprung a leak in late 2005, the risky yet refreshing ode to skateboarding was non-traditional in every sense of the word. It wasn't a club banger.

There were no major features or producers involved. No vixens in the video. No talk of cars or jewelry. Just a dope record about skateboarding and love. This single was an expression of who Lupe was at the time, and not something you're likely to see on a major label release in this day and age.

"Kick, Push" was a testament to just how big Lupe's buzz was at the time and how much the staff at Atlantic believed in him. The lyricism and production was rock-solid, so it was hard to deny its appeal, even though it catered to such a niche audience.—Andrew Barber

5. Twista f/ Yung Buk of PsychoDrama "Adrenaline Rush" (1997)

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Producer: The Legendary Traxster
Album: Adrenaline Rush
Label: Creator's Way, Big Beat, Atlantic


Adrenaline Rushis a classic album any way you slice it. Pretty much flawless front to back. It was a monumental Chicago street-oriented project and the tone of the album was set with the title track.

The song, which was literally recorded on the run, during dangerous times in the streets of Chicago, let listeners know that even though T made songs for the ladies, this was about to be some gangsta shit. He recruited fellow Westsider and fan-favorite Buk (of PsychoDrama)-the two equally charged MCs had a lot to prove and even more to get off their chests.

Anytime people ask for the old Twista and for him to return to his "roots," this is the track they always refer to. If there was ever a song that represented the sound of the streets of Chicago, this is unquestionably it.—Andrew Barber

4. Crucial Conflict "Hay" (1996)

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Producer: Wildstyle
Album: The Final Tic
Label: Universal


If you happened to flip on BET's Rap City in the summer of 1996, there's no way in hell you would've missed this energetic foursome bouncing around in matching overalls, carrying on about smoking hay in the middle of the barn. But let's get one thing straight-there were no barns on the side of town these guys were from.

After being discovered by Chicago businessman Shorty Capone, Crucial Conflict was courted by Suge Knight and other industry executives before signing with Fab 5 Freddy's Pallas Records. Their first introduction to the world was "Hay," a song dedicated to partaking in the herbal arts.

The track had so much bounce, soul, and harmony that it was able to covertly sneak on to radio airwaves across the country despite its drug-related content. The single eventually struck gold and climbed to No. 2 on Billboard's Hot Rap Singles chart.

Perhaps the best thing about Crucial Conflict was that despite their image as some fun-loving party boys, these guys were NOT to be played with or tested. But hey, if you ever have some "hay" and run into group member Cold Hard, he'll show you one hell of a time. He is the Mayor, after all.—Andrew Barber

3. Kanye West "Jesus Walks" (2004)

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Producer: Kanye West
Album: The College Dropout
Label: Roc-A-Fella, Def Jam


They said you can rap about anything except for Jesus. But Kanye did just that, and made it a smash hit/club banger. Kanye's third, and perhaps boldest, single from The College Dropoutwas definitely a crapshoot.

Can you imagine the meeting at Def Jam when they pitched this idea? "You're going to release a rap single about religion and shoot three videos for it? Suuuure." But 'Ye made the impossible possible when "Jesus Walks" shot to the top of the charts and was praised by critics and fans alike.

The pulsating drums, marching-band flavor, and background gospel chants were unlike anything else in hip-hop at the time. It's hard to imagine that countless artists passed on this beat and the track sat in the Kanye archives for years. Then again, it's debatable that any other artist could've done this justice.

"Jesus Walks" would go on to win Rap Song of the Year at the 2005 Grammy Awards, proving that dropping a song about Jesus in the oft-secular music industry could be done in a major way. Somewhere DC Talk is pissed.—Andrew Barber

2. Do or Die f/ Twista & Johnny P "Po Pimp" (1996)

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Producer: The Legendary Traxster
Album: Picture This
Label: Rap-a-Lot


In early 1996, Do or Die, a trio from the Westside neighborhood of Chicago, independently released an ode to pimpin' that quickly became a local hit. The song started to spread regionally and eventually caught the attention of James "J. Prince" Smith, the don of Rap-A-Lot Records.

Smith, who had close ties to Chicago, was so impressed with the song that he immediately signed the trio to RAL and had big plans for the single. As we've seen so many times on this list, the pairing of Do or Die, Traxster, Twista, and Johnny P was almost a surefire equation for success, and this was the first time the world was exposed to their chemistry.

Prince's intuition paid off, as "Po Pimp" became a smash on radio and television, reaching No. 1 on the rap charts and eventually going gold. The track is also notable for being the world's reintroduction to Tung Twista, who'd been off the national radar since '92.

It's no secret that T's closing verse was the scene stealer, and admit it-you've tried to nail that verse at least once. "Po Pimp" ushered in a new sound of Chicago hip-hop that became extremely popular and influenced music over the next few years.—Andrew Barber

1. Common "I Used to Love H.E.R." (1994)

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Producer: No I.D.
Album: Resurrection
Label: Relativity


The undisputed greatest Chicago hip-hop record of all time. An honor even Kanye would have to agree with. The acronym for H.E.R. has been disputed over the years (is it "Hearing Every Rhyme" or "Hip-Hop in its Essence is Real"?), but one thing is for sure: Common wasn't afraid to call a spade a spade.

Unhappy with the direction hip-hop was headed in, Common used the song as an extended metaphor for the genre, represented by a woman he once loved but had grown tired of due to H.E.R. recent actions. Das EFX and Onyx were used as examples, and subgenres like gangsta rap and G-funk were called into question.

Rash was salty that the industry gatekeepers were "letting all these goofies do her" and that show business had taken control of the culture. The song ruffled feathers across the industry and led Common into a heated battle with one of the all-time greats, Ice Cube (see No. 20).

On the last line of the final verse, Common and producer No I.D. let listeners in on the identity of the lady in question. And who they were talking about, y'all, was hip-hop.

Over the years, the track has been remade countless times, with the overall concept being used and abused, but none have come close or had the same impact as the original. We still love H.E.R.—Andrew Barber

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