It might pain the hip-hop purists to admit it, but rapping and advertising are inexorably linked. Rappers name-drop brands almost instinctively, while advertising companies co-opt their language, their image, and their cool.

This wasn't always the case. It took a while, with a few very visible missteps along the way, before the ad industry really recognized the marketing potential of hip-hop, but once they did the floodgates were forever opened. Money talks, and when it came calling, rappers blurted out slogans, donned ridiculous outfits, and gulped down beverages with a smile. Sometimes they even got to rap.

For many years it seemed like these ads would be left to our fading memories and scrapbooked Source magazine letters to the editor about the dangers of selling out. But today, thanks to technology, we can revisit two-and-a-half decades of hip-hop television advertising.

So Complex did just that and found 50 of the most memorable and culturally significant commercials to feature rap cameos, from the fan favorites to the embarrassingly bad and the downright bizarre.

Written by Andrew Noz (@noz)