Tim Meadows’ 8 Most Memorable Roles, Ranked

Tim Meadows may not be an A-list actor, but his contribution to American cinema cannot be overstated. As a character actor, Meadows has starred alongside some of Hollywood’s superstar actors. Making his on-screen acting debut in 1991, Tim Meadows has had a successful acting career spanning three decades.

In 2024, Tim Meadows reprised one of his most famous roles in film. He played Principal Ron Duvall in the 2004 Mean Girls alongside Tina Fey, Lindsay Lohan, Amy Poehler, and Rachel McAdams. Reprising the role, Meadows’ performance was nostalgic for fans and admirers of the actor. Here are 8 of Tim Meadows’ most memorable roles of his career.

Saturday Night Live (1991–2000)

Tim Meadows on Saturday Night Live

Tim Meadows began his career as a comedian. The actor and comedian began his career doing improvisation comedy at the Soup Kitchen Saloon. While in Chicago, Meadows was a The Second City comedy troupe member. His talents would get him a spot on NBC’s late-night live sketch comedy variety show, Saturday Night Live. For almost a decade, Meadows’ career was defined by his performance on SNL. It wasn’t only his breakout role, but it brought him international recognition. When Tim Meadows left SNL in 2000, he was the longest-serving member of the show. This record was later broken/surpassed by Darrell Hammond in 2005 and later, by Kenan Thompson in 2017.

The Ladies Man (2000)

Tim Meadows in The Ladies Man (2000)

Tim Meadows impersonated many celebrities during his time on Saturday Night Live. However, Meadows also played an original character, Leon Phelps. The character often regarded himself as The Ladies’ Man. In 2000, the year Meadows left SNL, a movie was made centered around the SNL character. Titled The Ladies Man, the sex comedy was co-written by Tim Meadows. It is also the actor’s first major role in a film.

The Cookout (2004)

Tim Meadows in The Cookout (2004)

Tim Meadows was part of the cast of Lance Rivera‘s comedy movie The Cookout (2004). Cast in a supporting role, Meadows played Leroy, cousin of the newly drafted basketball player for the New Jersey Jets. Cousin Leroy had hoped to be a lawyer but had failed his bar exams 15 times. By the end of the movie, he failed his sixteenth attempt at the exam but surprisingly found success as a published writer. His golf ball conspiracy book, White Balls & White Devils, became a bestseller.

The Bill Engvall Show (2007–2009)

Tim Meadows in The Bill Engvall Show

Tim Meadows joined the cast of The Bill Engvall Show in 2007. Meadows was cast as Paul DuFrayne in the TBS sitcom. His character was a friend of the titular character, Bill Pearson (Bill Engvall). Paul DuFrayne runs a hair transplant practice in the same building where Bill runs his family counselor practice. In an episode (“How Bill Met Susan”), it was revealed Paul DuFrayne initially wanted to be a doctor.

Grown Ups Movies

Tim Meadows in Grown Ups 2

For a newer generation of movie audiences, the Grown Ups films are easily Tim Meadows’ most recognizable roles. Meadows played the bald character Malcolm. He’s Dickie Bailey’s (Colin Quinn) former teammate and friend and a rival of Kurt McKenzie (Chris Rock). First appearing as the character in Grown Ups (2010), Meadows reprised the role in the 2013 sequel, Grown Ups 2.

Schooled (2019–2020)

Tim Meadows in Schooled

Tim Meadows first played the character of Jonathan “Andre” Glascott in the ABC period sitcom The Goldbergs. The character is the school’s guidance counselor, who also delivers pizza and gives guitar lessons for extra money. Although a recurring character in The Goldbergs, Andre Glascott became a main character in the direct spin-off sitcom Schooled. In Schooled, the character is introduced as the principal of William Penn Academy. The show originally aired on ABC from January 9, 2019, to May 13, 2020.

No Activity (2017–2021)

Tim Meadows in No Activity

In the CBS All Access run of No Activity, Tim Meadows starred alongside Patrick Brammall as a police detective. The series was greatly received by critics and audiences. However, the series was switched to a computer animation format for its fourth and final season, which Paramount+ picked up. While reprising their roles, Meadows and the other cast voiced the characters. As one of the main characters, Tim Meadows’ Judd Tolbeck character appeared in all four seasons of the series.

Hubie Halloween (2020)

Tim Meadows in Hubie Halloween (2020)

Before reprising the 20-year-old character in Mean Girls (2024), Tim Meadows’ most notable appearance in a movie was playing Mr. Lester Hennessey in the mystery/horror-comedy film Hubie Halloween (2020). Meadows played another bald character, although wearing a bald cap to appear so. His character was the husband of Maya Rudolph‘s character. Both characters are one of those in Salem, Massachusetts, who continuously play pranks on Hubie Dubois (Adam Sandler). After Hubie Halloween, Tim Meadows starred alongside Nicolas Cage, Julianne Nicholson, and Michael Cera in the black comedy fantasy film Dream Scenario (2023).

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