Once upon a time, In Living Color was the show you watched with your dad and that your mom silently disapproved of. It was raunchy enough to offend some, but funny enough to be the most hysterical thing on early-'90s television (and that's not even considering the box haircuts and parachute pants worn by the "fly girls," a troupe that did hip-hop dances between sketches and that launched J. Lo's career).
Though In Living Color featured a total of six members of the Wayans family (hats off if you can name them all!), it was the brainchild of Damon and his brother Keenan. And after seeing their respective work, one has to suspect that the real genius was Damon. Damon Wayans' bizarre and hysterical creations included the critical big screen disaster Major Payne (way funnier than people gave it credit for), and my personal all-time favorite recurring character on In Living Color, Anton the drunk hobo, who gave home improvement advice to the homeless. It was Damon Wayans at his best and worst: unbelievably politically incorrect, even offensive, yet almost impossible not to laugh at.
Wayans' penchant for going far over the line of decency hasn't always been funny. In 2008, he produced an online video called "Abortion Man" that features a superhero who helps men get their girlfriends' unborn children aborted by attacking the women. It might be a commentary on the brutality of abortion and its prevalence in the black community, or it might just be sick, misguided comedy. It's up on YouTube if you want to decide for yourself. —Sam Wardle