A Second City alum, the very funny Keegan-Michael Key has made the world laugh since his run on MadTV in the mid-2000s. Since then, he's become even more of a household name, especially thanks to his frequent collaborations with creative partner Jordan Peele. Their Comedy Central sketch comedy show Key & Peele served as a massive launchpad for both artists; Key even got to play Luther the Anger Translator from the show at a White House event with President Obama.
It's a busy time for Key — he's the voice of Toad in The Super Mario Bros. Movie and returns on season two of AppleTV+'s musical comedy Schmigadoon! Key's cinematic career has been varied, from cartoons to indie fare to tentpole comedies. All of his cinematic exploits are documented on Rotten Tomatoes.
9 'Keanu' (2016)
Rotten Tomatoes Score: 78%
Essentially a supersized Key & Peele episode, Keanu is a must-watch for cat lovers and Key and Peele enthusiasts alike. Rell (Peele) finds an adorable cat on his doorstep after a breakup, but when the cat is stolen, he recruits his cousin Clarence (Key) to track the missing kitty down. The duo ends up in a gang war, and shenanigans ensue.
Along with Key and Peele, the cast of this comedy is stacked with talent, including Tiffany Haddish, Method Man, Luis Guzman, and Will Forte. The action comedy caper has a 78% on Rotten Tomatoes. In addition to its solid reviews, the film was a modest box office success, making $20.7 million.
8 'Chip n' Dale: Rescue Rangers' (2022)
Rotten Tomatoes Score: 80%
The Disney+ exclusive Chip N' Dale: Rescue Rangers is an irreverent love letter to Saturday Morning Cartoons. 30 years after their show ended, Chip (John Mulaney) and Dale (Andy Samberg) have gone their separate ways in Los Angeles. When their animated costars start disappearing, the two must settle their differences and team up once again to save the day and track down their friends.
Key voices a handful of characters in the film, including a frog and Bjornson, the cheesemonger. Rescue Rangers has an 80% on Rotten Tomatoes, with critics and audiences alike enjoying its winking, nostalgia-tinged comedy. The film even won a Primetime Emmy for Outstanding Television Movie!
7 'Wendell & Wild' (2022)
Rotten Tomatoes Score: 81%
Coraline director Henry Selick returned to the realm of stop-motion animation with Wendell & Wild, a spooky-fun romp over a decade in the making. Teamed up once again, Key and Peele play the titular demons who try to make a deal with Kat (Lyric Ross), an orphaned punk teen at a boarding school run by a mysterious nun (Angela Bassett). Magic hair cream, a demonic theme park, and taking down the prison industrial complex all factor into the story that unfolds.
Wendell & Wild has a stellar 81% on Rotten Tomatoes. The film was praised for the vocal work of the cast (especially Key and Peele,) the gorgeous animation, the diverse cast of characters, and its punk rock aesthetic. However, the screenplay, co-written by Peele, was criticized as being a little too off-beat and hard to follow.
6 'Win It All' (2017)
Rotten Tomatoes Score: 85%
Joe Swanberg's comedy Win It All is a Jake Johnson vehicle with an intriguing premise. Gambling addict Eddie (Johnson) is trusted with an arrested acquaintance's duffle bag full of money – will he keep the bag safe til he's out of jail and can get a cut of the money? Or will Eddie blow it all on poker?
Key plays Eddie's Gambling Anonymous sponsor. Win It All has an 85% on Rotten Tomatoes. Critics especially praised the collaborative effort between Swanberg and Johnson.
5 'Jingle Jangle: A Christmas Journey' (2020)
Rotten Tomatoes Score: 89%
A steampunk Christmas adventure, Jingle Jangle: A Christmas Journey is a delightful holiday musical. Toymaker Jeronicus (Forest Whitaker) was the most popular toymaker in town until his apprentice Gustafson (Key) stole his greatest idea. Years later, it's up to Jeronicus' granddaughter Journey (Madalen Mills) and a magical invention Jeronicus hid away to stop Gustafson (Key) and bring Christmas magic back to their town.
A passion project for director/writer David E. Talbert, Jingle Jangle has a terrific 89% on Rotten Tomatoes. Critics especially praised the musical numbers and creative worldbuilding. It's a festive musical treat destined to become a classic.
4 'Dolemite is My Name' (2019)
Rotten Tomatoes Score: 97%
Based on a true story, Dolemite is My Name is a tribute to cult classic cinema and a terrific Eddie Murphy vehicle. Musician Rudy Ray Moore (Murphy) struggles to make it big in entertainment, so he creates an outrageous kung-fu-fighting alter ego, the titular Dolemite. The movie follows Rudy's attempt to make a big Hollywood movie about his character after success doing standup comedy as Dolemite.
Key plays Jerry Jones, a playwright Rudy enlists to write the screenplay for his movie. Dolemite is My Name has an incredible 97% on Rotten Tomatoes and is one of the highest-rated films of 2019. Critics especially praised Murphy, the entire cast's performances, and the immensely fun energy of the entire film.
3 'Toy Story 4' (2019)
Rotten Tomatoes Score: 97%
Pixar's flagship franchise added another adventure to the toybox with 2019's Toy Story 4. This entry in the series follows Woody (Tom Hanks), Buzz (Tim Allen), Forky (Tony Hale), and the rest of Bonnie's toys on a road trip as they reunite with Woody's old flame Bo Peep (Annie Potts) on a detour to an amusement park. Key voices Ducky, a plush animal Woody befriends on his adventure.
Key is once again paired in a comedy duo with Peele, who voices fellow stuffed animal, Bunny. With its 97% score on Rotten Tomatoes, Toy Story 4 was hugely successful with critics and audiences. It also upset Netflix's hand-drawn Klaus to win the Best Animated Feature Oscar in 2020; a fifth film is on the way.
2 'Don't Think Twice' (2016)
Rotten Tomatoes Score: 98%
Mike Birbiglia's Don't Think Twice is a slice-of-life ensemble comedy-drama about the ins and outs of The Commune, an improv troupe in New York City. The Commune anticipates a visit from talent-scouting staff from a Saturday Night Live-esque TV show. When troupe member Jack (Key) ends up cast on the series, the troupe starts attracting bigger crowds at their tiny venue – but are they only there to see Jack do one of his recurring characters from TV?
Don't Think Twice has a phenomenal 98% on Rotten Tomatoes. The indie film was praised for its writing, the chemistry of its ensemble cast (including Birbiglia, Key, Gillian Jacobs, Kate Micucci, and Chris Gethard), and its focus on the struggles of the creative process of theater artists.
1 'Teacher of The Year' (2014)
Rotten Tomatoes Score: 100%
Boasting a perfect 100% on Rotten Tomatoes, Teacher of the Year is a mockumentary that takes a look at the state of education in the United States via the antics at one California charter school. Mitch Carter (Matt Lescher) is a beloved English teacher and soccer coach at Truman High. When he's given the Teacher of the Year award by the state, he's also offered an opportunity for a higher-paying job, which he doesn't know if he should take.
Key plays Principal Ronald Douche (he insists it's pronounced "dow-shay") in this indie ensemble comedy, featuring Jason and Randy Sklar as a pair of not-very-helpful guidance counselors. The film won a few awards at festivals throughout 2014, including an Audience Choice award for best comedy at Newport Beach.
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