Meadows began performing improvisational comedy at the Soup Kitchen Saloon in Michigan. His start in show business came 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 often spoofed famous personalities including O.J. Simpson, Michael Jackson, Tiger Woods, Oprah Winfrey and Erykah Badu on Snl. He is also known for his original character Leon Phelps, "The Ladies Man," a 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.

[source: Comedy @ the Carlson website, 2019-Dec-30]