During his stint as ringmaster, he always found himself writing comedy and telling jokes, which later helped Mooney land his first professional work as a writer for Richard Pryor.

Mooney's childhood friends, gospel folk duo Joe and Eddie, first made him aware of Richard Pryor in the mid-1960s after seeing him perform in New York City.

Mooney also wrote for Redd Foxx's Sanford and Son and Good Times, acted in several cult classics including the Richard Pryor comedy films Which Way Is Up?, Bustin' Loose, and the cult satirical comedy Hollywood Shuffle, and portrayed singer/songwriter Sam Cooke in The Buddy Holly Story.

He was the head writer for the first year of Fox's In Living Color, inspiring the character Homey D. Clown, played by Damon Wayans.

Mooney later went on to play Wayans' father in the Spike Lee-directed film Bamboozled as the comedian Junebug.

As Negrodamus, Mooney ad-libbed the "answers to life's most unsolvable mysteries" such as "Why do white people love Wayne Brady?"

The top 25 moments included incidents involving Marion Barry, Terrell Owens, Wilson Goode, Michael Jackson, Flavor Flav, Whitney Houston, and Tupac Shakur.

[11] According to people who were in attendance, Mooney also made light of the death of Ross's ex-husband Arne Næss Jr., who fell while mountain climbing in 2004.

When Mooney was informed that Tracee Ellis Ross was in the audience, he stated: I didn't know ... her mama could've been in there, that's not the point.

[11] On November 26, 2006, Mooney appeared on CNN and talked about how he would stop using the word "nigga" due to Michael Richards's outbursts on stage at the Laugh Factory.

"[citation needed] On November 30, Mooney elaborated upon these remarks from his appearance on CNN as a guest of Farai Chideya on the National Public Radio program News & Notes.

[15] He declared that he would convene a conference on this controversial subject in the near future, as well as perform his first "n-free" comedy in the upcoming days.

On the BET special 25 Events that Mis-Shaped Black America, Mooney reiterated that he was no longer using the word.

[1] Mooney reflects on his childhood and some of the most notorious moments in his life, including organizing a performers' strike on the Comedy Store and publicly giving up the n-word after Michael Richards' onstage outburst.