The 50 Greatest Chicago Rap Songs

From Kanye hits to underground bangers, Fake Shore Drive counts down the Windy City's all-time best classics.

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Image via Complex Original
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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 that 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.

Words by Andrew Barber (@FAKESHOREDRIVE)

Homecoming

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

Year: 2007

Produced By: Kanye West


Album: Graduation

Label: Roc-A-Fella/Def Jam

Kanye West f/ John Legend "Home"

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).

#49. Yung Berg "Sexy Lady"

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#48. No I.D. f/ Dug Infinite "Real Weight"

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#47. Grav f/ Al Tariq & Lil Ray "City to City"

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#46. DA Smart "Walk Wit Me"

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#45. All Natural "50 Years"

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#44. Common f/ Kanye West "Southside"

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#43. Payroll "Never Change"

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#42. Rhymefest "How We Chill 1 & 2"

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Rhymefest f/ Juice "How We Chill Pt. 2"

Prior to winning a Grammy for penning "Jesus Walks" alongside Kanye West, Rhymefest was a beast in Chicago's underground and battle rap circuit. In 1997 he won the coveted Scribble Jam and released his first ever 12-inch, "How We Chill," a hometown ode: "This is how we chill with the boys/C-H is Chicago, I-L is Illinois." The single also included a sequel (which was probably more popular than the original) on the B-side featuring his longtime rival, Juice. Both "1" and "2" were produced by legendary Chi City production team the Molemen and gave listeners a bird's-eye view into the people, places, and neighborhoods that make Chicago tick. Earlier this year, 'Fest squashed his longstanding beef with Juice and formed the group BLX with Mikkey Halsted and Twone Gabz. He also recently announced his candidacy for 20th Ward Alderman of Chicago, so I guess that's how he's chillin' now.

#41. Just Ro f/ Common "Confusion"

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#40. Kidz in the Hall "Drivin' Down the Block (Low End Theory)"

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#39. Da Brat f/ The Notorious B.I.G. & Jermaine Dupri "Da B Side"

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#38. Kanye West "My Way"

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#37. Infamous Syndicate "Here I Go"

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#36. GLC "I Ain't Even On Yet"

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#35. L.E.P. Bogus Boys "Chicago Niggaz"

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#34. PsychoDrama "Do Whatcha Wanna Do"

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#33. E.C. Illa "On Ill"

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

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#31. Common Sense "Soul by the Pound"

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#30. Crucial Conflict "Bogus Mayn"

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#29. Do or Die f/ Twista & Johnny P "Still Po Pimpin'"

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#28. D 2 Tha S "Doomsday"

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#27. The Cool Kids "Black Mags"

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#26. Lupe Fiasco "Failure"

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#25. Twista "Overdose"

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#24. Shawnna "Gettin' Some"

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#23. Molemen f/ Juice "Freestyle or Written"

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#22. Bump J "Move Around"

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#21. Mikkey Halsted "Liquor Store"

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#20. Common "The Bitch in Yoo"

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#19. E.C. Illa "What You Be About"

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#18. No I.D. f/ Common & Dug Infinite "State to State"

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#17. Crucial Conflict f/ Toi "Ride the Rodeo"

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#16. Twista f/ Johnny P "Emotions"

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#15. Do or Die f/ Johnny P "Playa Like Me & You"

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#14. Lupe Fiasco f/ Matthew Santos "Superstar"

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#13. Common f/ The Last Poets "The Corner"

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#12. Da Brat "Funkdafied"

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#11. PsychoDrama "Magic"

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#10. Kanye West "Through the Wire"

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#9. Common "Resurrection"

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Common "Resurrection (Large Professor Remix)"

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.

#8. Twista f/ Kanye West & Jamie Foxx "Slow Jamz"

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#7. Kanye West "Can't Tell Me Nothin'"

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#6. Lupe Fiasco "Kick, Push"

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#5. Twista f/ Buk of PsychoDrama "Adrenaline Rush"

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#4. Crucial Conflict "Hay"

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#3. Kanye West "Jesus Walks"

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#2. Do or Die f/ Twista & Johnny P "Po Pimp"

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#1. Common "I Used to Love H.E.R."

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