The 25 best Chicago rap videos of all time

(Hype Williams/Roc-A-Fella Records)

Rap videos can be tricky to understand as an art form. If you aren't in tune with the culture, you might just dismiss them all as a cavalcade of ginormous butts, bottles, cars and one tough guy in the back row counting a large wad of money. (People in tune know that that's only true 89% of the time.) Chicago has a very storied history of quality rap videos from homegrown stars and it's high time we gave them some cultural appreciation. Here's my list for the 25 best Chicago rap videos of all time.

Honorable mention:

Kanye West, "Drive Slow"

Hollywood Holt, "Hollywood"

Kanye West, "Can't Tell Me Nothin’"

Kanye West, "All Falls Down"

Common, "Come Close"

Common, "I Want You"

Count, "10 Take Down Commandments"

Dude N'em, "Watch my feet"




25: Chance the Rapper, ‘Hey Ma’
(director: Elijah Alvarado)
One of Chicago's newest rap sensations crafts a loving tribute to his fam, his inspirations and Mommie Dearest. The clip is warm and showcases a lot of pics of Baby Channo.


24: Hot Stylz, ‘Lookin' Boy’
(director: Kai Crawford/Yung Joc)
Who's ready for a roasting session? The unique clip is a tribute to both the schoolyard game "the dozens"and that horrible "Yo Mama" show Wilmer Valderamma used to host on MTV2. A Chicago-style "Lookin' Boy" show? I'd watch that every day.

23: Just Ro, ‘Confusion’
(director: Samuel McQueen/Just Ro)
Here's a throwback for anyone who used to order videos off The Box. This classic Chicago clip blew up the airwaves in '96-'97 and features Common stealing the show in front of Lem's BBQ.

22: L.E.P Bogus Boys, ‘Going in for the kill’
(director: Coodie for Creative Control)
A narrative that wouldn't be far out of place in a Hughes brothers or Scorcese flick, the video shows a textbook robbery and how it can all go bad very quickly.