Wolf began his career performing stand-up in Los Angeles in the 1980s, and landed his first major television role as co-host (with Paul Provenza) on the Comedy Central variety series Comics Only in the early 1990s. In 1993, Wolf joined the writing staff of Saturday Night Live and also served for several years as head writer up until 1996.[1] In 1996, he joined the SNL cast as a featured player, before leaving the show in October of that same year. Since leaving SNL, he has collaborated with many of his former SNL co-workers, writing and directing films for SNL stars such as Adam Sandler, Chris Farley, Norm Macdonald, David Spade, and Rob Schneider.