Meadows began performing improvisational comedy at the Soup Kitchen Saloon. Meadows’ starts in show business was as a member of The Second City comedy troupe alongside future star Chris Farley. In 1991, Meadows landed a spot on Saturday Night Live and would go on to become a longtime cast member, appearing on the program until 2000. Meadows’ lengthy tenure on teh show was used as a gag in three monologues when former cast members Phil Hartman and Mike Myers returned to the show to host when Alex Baldwin hosted for his twelfth time.