Actor and comedian Charlie Day has graced television and movie screens globally since his first appearance in the 2000 television show Mary and Rhoda for ABC. That movie had a strong turnout in viewership, but the critical reaction was far from positive. Regardless of that, Day continued his career with some smaller roles in movies and television, but found his break in 2005 show It’s Always Sunny in Philadelphia. Day was an executive producer for the show and part of the main cast as the character Charlie Kelly, a member of the show’s friend group with a hidden plethora of unexpected talents.

It’s Always Sunny in Philadelphia was a smash hit and ran for 14 seasons, cementing Day’s career as an actor and serving as a launching pad for his future endeavors. While he may not have continued deeply into television, he has served some iconic characters in movies like Monsters University, Pacific Rim, and the much-anticipated upcoming Super Mario Bros. film with Chris Pratt. While fans can’t wait for Day to be the voice of Luigi in the Mario movie, he has had several memorable roles up until now. These are Charlie Day's best performances, ranked.

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6 The Hollars

Three men sit on gymnasium seats.
Sony Pictures Classics

John Krasinski, of The Office fame, directed the 2016 comedic drama The Hollars. He also starred in the lead role alongside Anna Kendrick and Sharlto Copley. He portrays a graphic novelist who discovers his mother is dying of a brain tumor, so when he reunites with family, quite a bit of drama from the past resurfaces. Old girlfriends who are now married, failing businesses, and classic family issues come to light in this film. Charlie Day plays the husband of John’s ex-girlfriend, who has a strong suspicion that something is wrong with their marriage.

5 The Lego Movie

Two Legos hold hands. One is a man and the other a woman.
Warner Bros. Pictures

The Lego Movie is technically animated, so Day does not physically act in it. But his character, Benny, is very lovable, and it is pretty hard not to like him as a character. An ordinary Lego man (Chris Pratt) discovers people believe him to be the chosen one in a prophecy, and so when a force of evil comes to antagonize the land, it is up to this Lego man to save the world. The Lego Movie is something that many may roll their eyes at or think that it is a low-quality kid film, but it is surprisingly good. Both adults and kids alike can enjoy this movie, that is for sure.

4 Pacific Rim

Guy with tattooed arm explains something vibrantly.
Warner Bros. Pictures

Guillermo del Toro’s Pacific Rim was released in 2013 with the main cast consisting of Charlie Day, Charlie Hunnam, Idris Elba, and Rinko Kikuchi, among others. The movie drifts into the Japanese genre of films where giant monsters attack the earth. In this story, it is sea monsters attacking from the bottom of the Pacific Ocean, and the humans need to find a way to get rid of their new unwanted friends. Day portrays Dr. Newt Geiszler, one of the scientists studying these monsters. With a personality larger than life, vaguely reminiscent of Guy Fieri as he cycles through moods of seriousness and humor, Day created an iconic character that would also appear in the sequel Pacific Rim 2: Uprising.

3 Fist Fight

Man sips coffee with raised eyebrows.
Warner Bros. Pictures

Charlie Day served as the executive producer of Fist Fight, which was released in 2017. He also starred in the movie with the rapper-turned-actor Ice Cube, creating an unlikely combination between the two that works quite well. Day plays Andy Campbell, an English teacher waiting for news about his wife’s pregnancy as the students pull off a senior prank. Strickland, a history teacher (Ice Cube), has a fiery temper, and when a student tries to pull a prank on him, it creates a situation where Strickland loses his job and challenges Campbell to a fist fight after school. The film didn’t perform well at the box office, nor was it popular with the critics, but it held its weight in comedy.

2 Horrible Bosses

Three men look into car trunk.
Warner Bros. Pictures

Released in 2011, before Charlie Day began to get into the swing of the movie-making world, Horrible Bosses was released and became a box office hit. The movie follows a group of men, played by Patrick Bateman, Kevin Spacey, and Charlie Day, that delves into black comedy territory when they decide to murder their bosses. While Horrible Bosses is an exclusive boys’ club, it constructs environments that are both comedic and suffocating at the same time.

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1 It's Always Sunny in Philadelphia

Two men point at each other confused.
FX Productions

It’s Always Sunny in Philadelphia is one of the staple shows to come out of 2000s American television. The show ran for 15 seasons before bowing out and concluding its run. A good portion of the writing was done by the actors who starred in the show, like Charlie Day. Day’s performance as Charlie Kelly is his most iconic performance, if not the defining performance of his career so far. Charlie is an eccentric character with nuance to his details and backstory, creating a highly original and memorable character.