In 2004, "Chappelle's Show" was one of the most popular shows on basic cable and a huge money-maker for Comedy Central. Chappelle displayed a willingness to plunge into depths of racial satire and N-word usage that few were willing to touch.

But in 2005, during production of the show's third season, Chappelle shocked the entertainment world by abruptly leaving the show. In an interview with Time Magazine, Chappelle said he had left the show and had flown to South Africa to get away from the overwhelming fame he had built.

In February 2006, Chappelle spoke more in-depth about the show during an interview with Oprah Winfrey. He mentioned that while filming a sketch in which a pixie in blackface tempts him to act in ways that perpetuate stereotypes, a white crew member laughed in a way that made him feel uncomfortable. Chappelle began to wonder if he was reinforcing stereotypes rather than combating them.

In the following years, Chappelle chose to continue his career in comedy to free him from the attention that had unnerved him. His standup appearances were often confined to Los Angeles and went largely unannounced, though he did make several appearances on "Inside The Actors' Studio," including one in which he got the chance to interview the show's host, James Lipton.

In 2013, Chappelle slowly began to return to the limelight, starting with headlining a nationwide comedy tour with Flight of the Conchords. Unfortunately, one show quickly got ugly after hecklers in the crowd began chanting lines from "Chappelle's Show," which resulted in Chappelle ranting about the hecklers the following night at a Chicago show. That audio was later leaked onto a standup comedy blog.

Still, Chappelle's return took flight in 2014, as he made the cover of GQ, appeared on "The Late Show With David Letterman," and performed ten sold-out shows at Radio City Music Hall.

Chappelle even made a return to the big screen, playing a minor role in Spike Lee's "Chi-Raq" as a one of the gangbangers who are denied sex by the women of Chicago until the violence stops. Sample line from Chappelle: "This situation is out of control... because I'm in front of an empty stripper pole!"

Now Chappelle is making his biggest TV appearance since his days of playing Rick James and blind black KKK members by hosting the first post-election "SNL" episode. If it is anything like what we've come to expect from him, "SNL" may have some of its most biting material in years in store for us.