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.

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.