Meadows' start in showbiz 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. (This was the record for the longest tenure on the show until it was surpassed by Darrell Hammond in 2005.) Meadows' lengthy tenure on the show was used as a gag in two monologues when former cast members Phil Hartman and Mike Myers returned to the show to host. Meadows' many impressions on the show included Michael Jackson, Dennis Rodman, O.J. Simpson, and Oprah Winfrey.