In his first official show in the city in ten years, Chappelle was smoking cigarettes as he flipped between prepared jokes and riffs on everything from President Barack Obama to gay rights.
Chappelle took a break from comedy in 2005 when he quit Chappelle's Show and abandoned a $50 million offer from Comedy Central. Suspected reasons for his departure from the television and comedy business were his growing success and the pressure to hold it.
During his show he spoke briefly about two things he rarely mentions: his family and his religion. Chappelle converted to Islam in 1998. Chappelle and his wife Elaine have three children and he dedicated a good portion of his riffs to them.
Though people thought he was crazy when he quit in his prime, Chappelle said there was a method to his madness.
"When you see Half Baked 2, make no mistake about it, I have completely run out of money," he joked. "I am just back out here to make enough money to disappear again."
The eight-day run at Radio City Music Hall will include musical performances from Janelle Monae, Nas, The Roots, and Erykah Badu.
Notable deaths of 2014 [PHOTOS]