John Mayer in 2006

John Mayer the Comedian

The singer – who has appeared on Comedy Central'sChappelle's Show and filmed his own VH-1 comedy special – begins performing little-announced gigs atstand-up comedy venues in L.A. and New York. "Everyone connected to my well-being and on my payroll says stand-up is terrible," he tells Rolling Stone(which puts him on the cover as one of the generation's "New Guitar Gods"). "When I say, 'I'm doing stand-up tonight,' they hear, 'I'm going to start heroin.'" His frequently risqué routines get Mayer in trouble, most notably when reports surfaced that he'd used the n-word on stage.