Chappelle has performed only sporadically since he walked away from his Comedy Central sketch comedy series, "Chappelle's Show," in 2005. He is reported to have been living in rural Ohio for the last few years.
The Los Angeles Times said Chappelle recently played three unannounced dates at the Comedy Cellar, where his famously funny friends Rock, Kevin Hart, Marlon Wayans and Paul Mooney, turned up to support him.
During one performance, Chappelle indicated he didn't have much lined up in the way of work and might be open to getting on stage with Rock.
"After next Tuesday, I'm free for like 11 years," Chappelle said, to which Rock replied, "By Halloween I could do dates," the Times reported.
"I'm in," Rock said.
The Times said neither Rock's representative nor two publicists who previously worked with Chappelle responded to requests for comment about the possibility of a tour.