Summary

• Charlie Day has established himself as a comedic performer in both film and television, with a knack for physical comedy and over-the-top characters.
• While Day's directional debut, Fool's Paradise, missed the mark in terms of humor, it showcased his skills as a director and his passion for satirical takes on celebrity culture.
• Day's success extends to voice work in children's entertainment, including his standout role as Luigi in The Super Mario Bros. Movie, demonstrating his ability to bring his unique comedic timing to animated films.

In recent years, Charlie Day has revealed himself as one of the best comedic performers around and has played roles in a variety of incredible movies. Having first come to the audience’s attention as the dim-witted co-owner of Paddy’s Pub on It’s Always Sunny in Philadelphia, Day has managed to carve out an impressive film career while consistently delivering new seasons of the sitcom that he stars in, produces, and writes with his co-stars Glenn Howerton and Rob McElhenney. Day’s skill for physical comedy, recognizable voice, and over-the-top eccentrics have slowly turned him into a major star.

Day has played lead roles in major Hollywood comedies and has also found great success with voice work in children’s entertainment. While Day’s latest feature Fool’s Paradise, which he wrote, directed, and starred in, unfortunately missed the mark, he has also seen major success in movies like Horrible Bosses and The Super Mario Bros. Movie. A likable, funny, and at times vulnerable actor of great skill, the best of Day’s movies have showcased his unique talents and demonstrated his ability to add his idiosyncratic comedic style to every part he played.

10 Fool’s Paradise (2023)

Charlie Day as Latte Pronto

Despite boasting an incredible cast, the directional debut from Charlie Day, Fool’s Paradise, failed at its most important task: Being funny. With a committed performance from Day as Latte Pronto, a mute mental patient who became a movie star, Fool’s Paradise was a satirical take on celebrity culture that paid homage to Buster Keaton and Hal Ashby’s Being There. A passion project for Day, Fool’s Paradise had its merits, but many sequences fell flat, and, although he showcased accomplished skill as a director, his script failed to live up to even the worst episodes of It’s Always Sunny in Philadelphia.

9 Fist Fight (2017)

Charlie Day as Andy Campbell

As a comedy about teachers fighting like school kids, Fist Fight would have been better as a five-minute skit than a feature film. Starring Charlie Day and Ice Cube, Fist Fight worked best when you just accepted its silly concept and enjoyed the laughs along the way. With enough R-rated humor to sustain its 90-minute runtime, Fist Fight showcased Day’s ability to hold his own in a mainstream comedy. While Fist Fight won’t go down in history as one of the all-time great comedies, there are worse ways to pass the time.

8 Horrible Bosses 2

Charlie Day as Dale Arbus

While Horrible Bosses 2 felt like an unnecessary sequel, the trio of Charlie Day, Jason Bateman, and Jason Sudeikis was still a winning combination, and it was enjoyable to see them share the screen again. Unfortunately, Horrible Bosses 2 lacked the narrative hook of its predecessor and through an overuse of offensive humor failed to justify its existence. Horrible Bosses 2 confirmed that if this comedic trio wanted to keep working together, they should star in a new original movie instead of rehashing jokes for an inferior sequel.

7 Hotel Artemis (2018)

Charlie Day as Acapulco

Charlie Day stepped outside his comfort zone of playing a likable everyman to portray the obnoxious arms dealer Acapulco in Hotel Artemis. In a supporting role opposite Jodie Foster, Day added his unique comedic sensibility to an action movie that was more serious than what he had been used to. Hotel Artemis brought to mind other movies like John Wick, and while, in the end, the true star of the film was Foster, Day demonstrated his ability to act as an important secondary character and contribute his unique comedic timing to this enjoyable crime thriller.

6 The Lego Movie (2014)

Charlie Day as Benny

The Lego Movie managed to capture a playful childlike sense of adventure in a surprisingly thoughtful narrative that pleased adults and kids alike. Charlie Day stood out as Benny, a Master Builder obsessed with spaceships, whose over-the-top love for construction added to The Lego Movie’s theme of the power of creation. With such a unique voice and expressive energy, Day’s skills as a voice actor worked well in children’s entertainment, and his success in movies like The Lego Movie points to a fruitful career pursuing voice work as well as live-action comedy.

5 Pacific Rim (2013)

Charlie Day as Dr. Newt Geiszler

As director Guillermo del Toro’s love letter to the Japanese Kaiju giant monster genre, Pacific Rim was a blockbuster smash that delivered both visual spectacle and a compelling narrative that paid homage to mecha and anime media. An important aspect of the success of Pacific Rim was Charlie Day as Dr. Newt Geiszler, a Kaiju-obsessed scientist who uncovered the monsters purpose in their world. Day brought an everyman sensibility to his role that helped ground Pacific Rim within its world, he provided exposition to the lore of the Kaiju and even returned for the sequel Pacific Rim: Uprising.

4 Monsters University (2013)

Charlie Day as Art

A prequel to Pixar’s classic movie Monsters, Inc., Monsters University delivered thoughtful family entertainment, even if it could never quite match up to the magic of its original. With a whole host of new characters joining Mike and Sulley, Charlie Day stood out as Art, an unusual purple arch-shaped monster studying New Age Philosophy and a member of the Oozma Kappa fraternity. Day added heart, humor, and wholesomeness to Monsters University and the film acted as the first clue to his incredible potential as a voice actor.

3 The Super Mario Bros. Movie (2023)

Charlie Day as Luigi

The Super Mario Bros. Movie was a smash success with audiences that has remained extremely popular on Netflix. Propped up by voice work from Chris Pratt as Mario, Jack Black as Bowser, and Charlie Day as Luigi, this colorful adventure proved that Nintendo’s mascot could finally leap from the world of video games into blockbuster cinema. Day as Luigi was a stroke of genius and, if anything, he was underused in The Super Mario Bros. Movie and would be well-suited to leading a Luigi’s Mansion spin-off movie in the future.

2 Horrible Bosses (2011)

Charlie Day as Dale Arbus

Horrible Bosses was a surprise box office success that proved the comedic potential of its three stars Charlie Day, Jason Batman, and Jason Sudeikis. A hilarious story of three friends plotting to murder their overbearing and abusive bosses, Horrible Bosses was the first time a main cast member from the It’s Always Sunny in Philadelphia crew managed to find mainstream commercial success in a major Hollywood movie. With Horrible Bosses, Day proved himself capable of taking on larger roles outside his acclaimed sitcom, and the film acted as a watershed moment in the progression of his career.

1 I Want You Back (2022)

Charlie Day as Peter