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The 25 best Chicago rap videos of all time

January 28, 2013|Ernest Wilkins, @ernestwilkins | RedEye Sound Board | RedEye

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.

21: Lupe, ‘Hip Hop Saved My Life’
(director: Dr. Teeth)
This is a wonderful example of a video that lets the storytelling contained within the song do the talking. With a surprise appearance from Houston rap legend Bun B, we see Lupe's words come to life on screen.


20: Kanye West, ‘The Workout Plan’
(director: Kanye West and Little X)
Easily Kanye's funniest video, and almost his most star-studded with appearances from Tracie Ellis Ross, Vida Guerra, Fonzworth Bentley, John Legend and the late Anna Nicole Smith in a real WTF? moment.

19: Pac Man, ‘Dro Style’
(director: Dirty P. Thirty)
Time for a history lesson. The Money Dance craze sweeping the city the past couple of years? It was actually originally called "Dro Style" and was popularized by Pac Man, a rapper from the South Side who tragically befell the same fate of far too many others due to street violence. This video is a legacy and a testament to his dance movement.

18: The Cool Kids, ‘Black Mags’
(director: GL Joe)
Ah, 2003. When Mikey Rocks and Chuck Inglish dropped this ode to riding on their bikes around town, the national audience stood up and took notice. Chicago's second big rap wave followed, paving the way for a significant amount of attention on the city and a really boring argument on what exactly "hipster rap" is. Regardless, it's a classic clip.

17: Chief Keef, ‘I Don't Like’
(director: DGainz)
Ah yes, the biggest hit from the most controversial rap artist of the last three years. This is the first time a major audience got a look at the G.B.E boys and with 22 million views of this video to date, it's safe to say they liked what they saw. As far as narrative? Um, they all don't like wearing shirts. Can't say I blame them, honestly. Shirts suck.

16: Kanye West, ‘Flashing Lights’
(director: Kanye West)
Sometimes, you don't need a lot of time to get your point across. In this brief-yet-memorable clip. Mr. West introduces us to a lady with a whole lot of junk in the trunk. (I mean that in every possible way you can think of.) Confused? Watch the clip and find out.


15: L.E.P. Bogus Boyz, ‘Trading Places’
(director: Coodie and Chike for Creative Control)
Wow. This cautionary rap tale of what happens when a kidnapping goes wrong is a jarring clip. Craziest thing? It's based on a true story. You won't see the ending coming, trust me.

14: Shawnna, ‘Gettin' Some’
(director: Chaka Zulu)
Holding it down for the ladies, Buddy Guy's baby girl takes us from the hair salon (Did you catch the cameo from Teefa, her partner in Infamous Syndicate?) to hanging with her DTP (the entire crew shows up, that's 2 Chainz back there!) and Hustle Period family. (Sidenote: Gents, skip to 2:45 and thank me later.)

13: Twista, ‘Emotions’
(director: Twista)
Sharing a tale of lady issues with his pals Speedknot Mobsta Liffy Stokes and The Legendary Traxster, Twista takes us on a ride through pure emotions. Another classic Chicago clip.

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