10: Crucial Conflict, ‘Hay’
(director: Fab 5 Freddy)
IN THE MIDDLE OF THE BARRRRRRRNNNNN ... besides being one of the best Chicago rap songs ever, this clip features a rollicking good time in a farmhouse and was a big hit on BET, MTV and the Box way back when. Now if you’ll excuse me, I'm off to go dig out my overalls.
9: Da Brat, ‘Give it to you’
(director: Jermaine Dupri)
Featuring appearances from MC Lyte, Jermaine Dupri on drums (seriously), Bill Bellamy, Mary J. Blige, T-Boz, Goodie Mob, Puffy, Biggie and MANY more, this video was a huge look for a Chicago artist and one of the few rap videos that looked like a crazy party when the cameras stopped rolling.
8: Kanye West, ‘Touch The Sky’
(director: Chris Milk)
Evil Kanye-vel! The vintage clip features the debut of Lupe Fiasco, a crazy appearance from Nia Long and Tracie Ellis Ross and co-star Pamela Anderson totally frenching Kanye before he touches the sky. Also, the Jim Brown mutton chops Kanye sports here are top-notch.
7: Kidz in the Hall, ‘Driving Down the Block’
(director: Ethan Lader)
Let's take a walk down to the used-car lot, shall we? Shot in the style of one of those terrible late-night informercials, Naledge rhymes about cruising through Chicago's streets and Double O wears the funniest mustache I have ever seen. It's like if Issac from "The Love Boat" and Wilford Brimley had a kid. Just wonderful.
6: Common, ‘I Used to Love H.E.R.’
(director: Chris Haliburton)
What else can be said about this video and song? Com's touching tribute to Lady Hip-Hop off the classic "Resurrection" album walks us through their relationship, for better or for worse.
5: Kanye West , ’Through the Wire’
(director: Coodie and Chike)
This video is amazing. Charting how Kanye West went from producer to rapper on his first album in a scrapbook format, the flick even has footage from him in the hospital after his accident and him getting his Roc-A-Fella chain from Dame Dash. Also features a great appearance from comedian DeRay Davis and a lovable crackhead.
4: Mikkey Halsted, ‘Liquor Store’
(director: Rico and Da Visionaryz)
One of the great missions of a music video is to bring the story of the song to life. This video accomplishes that and more. Deemed controversial upon its release, the video sparked conversation about the relationship between Blacks and Arabs in Chicago's poorer neighborhoods.
3: Do or Die, ‘Po Pimp’
(director: Daniel Zirilli)
Did you know that other than being Chicago rap legends, the gents of Do or Die are also genies? They granted hood wishes with just a flip of a coin in this video. The widespread attention this video got turned a lot of heads onto the Windy City and even gave Twista his debut to a big audience. From the pool party to Johnny P's shirt/shorts combo, this one is a bona-fide 5-star classic.
2: Kanye West, ‘Homecoming’
(director: Hype Williams)
This isn't a video, it's a love letter to Chicago. Kanye raps about his love of the Second City while iconic shots of local landmarks take your breath away, looped in with that guy from Coldplay tickling the ivories. This might be the best Chicago rap video ever ...
1: Common, ‘The Corner’
(director: Kanye West)
Except it isnt. Now, you're asking, how does this beat out "Homecoming”? Well, it accomplishes several goals. Chicago's landmarks are one thing, but it's the people who reside here that make it what it is, for better or worse. A video that takes place in the dead of Chicago winter and still manages to make people want to move here, features one of the icons of the scene interacting with the streets that made him AND manages to show off both sides of Chicago (both beautiful and gritty?). This is the best Chicago rap video of all time.
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