We often use this space to discuss how Chicago's architecture and neighborhoods are seen in movies and TV shows. But I think the best view comes from hip-hop music videos--especially those by Chicago artists.
Kanye West directed the above video for rapper Common's 2005 cut "The Corner."‚ West sees Chicago the way a native does: at times cold and foreboding, yet beautiful. The opening helicopter shot of the domed Adler Planetarium sitting out in an ice-over Lake Michigan is brilliant, as are the cuts to what I think is a 1981 Oldsmobile rolling down Garfield Blvd on 20" rims. Navy Pier and the high-rises of north Lake Shore Drive are seen, as are the Regal Theater near 79th and Stony Island, the corner of 79th and Cottage Grove.
The next offering also from 2005: "So Sexy," by Twista (featuring R. Kelly).‚ Almost the entire video takes place at Wabash and Wacker along the river, but there is still some good images of Marina City, 35 E. Wacker and the now-demolished Chicago Sun-Times building:
Back to Kanye for 2008's "Homecoming" video. Nice use of black-and-white photography showcases Millennium Park, the DuSable Museum, and Tribune Tower. The shot of Kanye walking beneath the Cloudgate sculpture (aka, "The Bean") is impressive: