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 67% true.) 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.
Kanye West, "Drive Slow"
Hollywood Holt, "Hollywood"
Kanye West, "Can't Tell Me Nothin’"
Kanye West, "All Falls Down"
Common, "Come Close"
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’
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’
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.
12: EC Illa, ‘On Ill’
(director: EC Illa)
This one is a personal favorite as it's the first rap video from a Chicago artist I ever saw. The visual is gritty and showcases a Chicago that a lot of people aren't that familiar with. Also, there's mad breakdancing and graffiti tags. The ELEMENTS OF HIP-HOP, people!
11: Lupe Fiasco, ‘Kick Push’
(director: Chris Adams/Hannah McDowell)
Get out your grip tape and gold Casio watch, this clip is a love affair to all things skateboarding. Lupe's ode to sidewalk surfing was so impactful, people were actually picking up boards and immediately going outside to embarrass themselves.
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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