In 2006, Wilmore began appearing regularly on The Daily Show, where he is billed as the "Senior Black Correspondent" or a derivative form of the title, such as the "Senior Executive Commander-in-Chief Who Happens To Be Black Correspondent" following the election of Barack Obama. His work on the show frequently centers on humorous observations of the Black experience in American society. In January 2009, Hyperion published Wilmore's I'd Rather We Got Casinos: And Other Black Thoughts, a political humor book described by Booklist as "a faux collection of articles, essays, radio transcripts, and letters exploring the more ludicrous angles on race." Wilmore originated the titular phrase I'd Rather We Got Casinos in a January 2007 Daily Show appearance.
As of 2012, Wilmore starred in the Showtime special titled Race, Religion and Sex that was shot in Salt Lake City, Utah. Part stand-up show, part town-hall meeting, the special is a precursor for a possible series that could take place in different cities.
^Black History Month (video clip from episode of television show). The Daily Show. Comedy Central. January 31, 2007. "Jon Stewart: Don't you feel that black history month serves a purpose? Larry Wilmore: Yes, the purpose of making up for centuries of oppression with 28 days of trivia. You know what? I'd rather we got casinos."