Adam Sandler

Arguably the most successful of the Saturday Night Live alumni, Adam Sandler first appeared on the show in 1991 after initially being hired as a writer. He became a favorite in the cast when his performances of "The Thanksgiving Song" and "The Chanukah Song" (both of which he wrote) appeared on Weekend Update and immediately made him a pop-culture touchstone among college kids at the time. After getting fired from S.N.L. in 1995, Sandler went on to an enormously lucrative film career, writing, producing and appearing in semi-cult faves Happy Gilmore, Billy Madison and The Wedding Singer, then in the blockbuster The Waterboy, the critically well-received Punch-Drunk Love and family vehicles Big Daddy, Click and Bedtime Stories. He took on a semi-dramatic role in Judd Apatow's '09 film Funny People. Throughout his career he has also released steadily selling sketch comedy albums, starting with They're All Gonna Laugh at You! in 1994, where he spotlights a much darker, raunchier style.