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After studying television and radio broadcasting at Wayne State University, Meadows began performing improvisational comedy at the Soup Kitchen Saloon. Meadows' start 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. (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 three monologues when former cast members Phil Hartman and Mike Myers returned to the show to host, and when Alec Baldwin hosted for his twelfth time.
Tiger Woods, Oprah Winfrey and Erykah Badu on SNL, and one time remarked that he had no character that was identified to him, such as Wayne and Garth being identified to Mike Myers and Dana Carvey. Eventually he did get an original character with Leon Phelps, "The Ladies' Man", a perpetually horny talk show host who believed himself to be the living definition of what females search for in a man. The sketch/character was adapted into a 2000 film, The Ladies Man, which followed the character's attempts to find love and a suitable outlet for his beloved radio program. Despite a surprise guest appearance by Meadows on Saturday Night Live immediately following his departure to promote the movie, it was not well-received by critics or fans and subsequently flopped at the box office. It has, however, become a cult classic on DVD and cable. In 2001 he co-starred in Three Days (2001); in 2003 he appeared as Miles McDermott in The Even Stevens Movie.
Meadows has appeared in other feature films, including Coneheads, It's Pat, and Wayne's World 2, all of which were based on popular SNL characters and had varying rates of success. Most recently he was in the 2006 film The Benchwarmers alongside his former SNL co-stars Rob Schneider and David Spade. He was also featured in CBS's Gameshow Marathon (summer 2006), has appeared on The Colbert Report in the recurring role of P.K. Winsome (who made an appearance at the Rally to Restore Sanity and/or Fear), and starred in The Bill Engvall Show. He is also a frequent guest on the Late Late Show With Craig Ferguson as a comic field reporter. On May 31, 2008, Meadows threw out a ceremonial first pitch and conducted the seventh-inning stretch at Wrigley Field during a Chicago Cubs game against the Colorado Rockies.