Meadows began performing improvisational comedy at the Soup Kitchen Saloon.[3] Meadows's start in show business was in Chicago 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 went on to become a longtime cast member, appearing on the program until 2000. (Meadows was on the show for 10 seasons; this was the record for the longest tenure on the show until it was surpassed by Darrell Hammond in 2005, whose record was also surpassed by Kenan Thompson in 2017.) Meadows's 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 12th time.
During his time on SNL, Meadows often spoofed famous personalities, including Oprah Winfrey, Erykah Badu, Michael Jackson, and Tiger Woods, and one time was a quick-change artist to pull off an impersonation of both O. J. Simpson and Al Cowlings within the timespan of one SNL skit. Some skits had Meadows playing a fictionalized version of himself, such as being a fan of ice hockey on Weekend Update, stating his dissatisfaction with the 1994 NHL lockout and remarking, "What am I supposed to do about this; watch basketball?" Another sketch as himself was introducing the entire SNL cast as their most famous characters, such as Wayne and Garth, or Melanie Hutsell as Jan Brady in a sing-along denouncing the 1992 Los Angeles riots, which ends with Meadows remarking, "This is personal to me...mainly because I don't have an SNL character to play!" Eventually, he did get an original character with Leon Phelps, "The Ladies' Man", a perpetually sexual arousedtalk-show host who falsely believed himself to be the living definition of what women search for in a man. The 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. In 2001, he co-starred in Three Days; in 2003, he appeared as Miles McDermott in The Even Stevens Movie.
In 2014, Meadows co-starred alongside Casey Wilson and Ken Marino in the short-lived NBC sitcom Marry Me. Dan Bucatinsky and he played "the Kevins", the gay dads of Annie (played by Wilson), who are both named Kevin. Since 2013, he has appeared in a recurring role on the ABC sitcom The Goldbergs, playing Mr. Glascott, the high school's parrot-owning guidance counselor. In 2016, he began starring in the FOX live-action/animation hybrid Son of Zorn opposite Cheryl Hines and Jason Sudeikis. He also had a recurring role in Brooklyn Nine-Nine as Jake Peralta's cannibal prison cellmate.
On February 17, 2023, Meadows was announced to reprise his role as Principal Ron Duvall from the first Mean Girls film in the stage-to-screen adaptation of the Broadway musical.[5]
Personal life
Meadows married Michelle Taylor in 1997, and they had two sons together. They divorced in 2005.[6]