In 1985, Goodman originated the role of Pap Finn in Big River. For his role, he received a Drama Desk nomination for Best Featured Actor in a Musical; he is also featured on the Original Broadway Cast Recording. He had a long history of appearances on late night comedy shows and was the first guest on Late Night with Conan O'Brien, which won him the series' "First Guest Medal" (Goodman joked he would pawn the medal for a bottle of cheap Scotch). Goodman has hosted NBC's Saturday Night Live 13 times, while also making seven cameo appearances as Linda Tripp during the Monica Lewinsky scandal and cameoing on the season 28 finale hosted by former SNL cast member Dan Aykroyd. With little to no experience in TV comedy, Goodman auditioned to be a cast member for Jean Doumanian's tumultuous 1980–1981 SNL season and was rejected, along with up-and-coming comedians Jim Carrey, Paul Reubens, and Robert Townsend.