In the 1960s, Krassner was a regular contributor to several men's magazines including "Cavalier" and "Playboy". "Cavalier" hired Krassner for $1,000 per month to write a column called "The Naked Emperor." In 1971, Krassner worked as a weekend radio personality and disk jockey at San Francisco's ABC-FM radio affiliate, KSFX, (subsequently KGO-FM). Under the pseudonym "Rumpelforeskin", he satirized culture and politics while espousing his atheism. He was also a contributor to early issues of "Mad magazine". He often appeared as a stand-up comedian, and he was among those featured in the 2005 documentary "The Aristocrats". Krassner was also a prolific lecturer and was a frequent speaker at both the Starwood Festival and the WinterStar Symposium. In 1998 he was featured at the Rock & Roll Hall of Fame with Wavy Gravy during their exhibit entitled "I Want to Take You Higher: The Psychedelic Era 1965–1969". He was a columnist for "The Nation", "AVN Online" and "High Times Magazine". He also blogged at "The Huffington Post" and "The Rag Blog".