
Charlene Badasie
Like most actors, Matthew Perry began his career with several small roles on television and in film. While his roles in the '80s may not have been all that memorable, the actor finally got his big break in 1994 when he was cast as Chandler Bing in Friends (1994). After that, Perry became a household name and went on to star in some really great movies.
The release of the Peacock documentary, Matthew Perry: A Hollywood Tragedy (2025) reignited interest in the late actor's long career. It would be difficult to list all his roles, but here is a helpful guide that includes Perry's best movies and TV shows, ranked from best to worst, during and after his tenure on Friends. From Hulu to Max, most platforms house a Perry film or two.
6. Mr. Sunshine (2011-2012)
After Friends ended, Perry found himself starring in the sitcom Mr. Sunshine, which he also co-created. The story, which only lasted one season, follows Ben Donovan (Perry), a slightly self-absorbed manager of a second-tier sports arena called the Sunshine Center. The show is essentially a workplace comedy, with Perry's character trying to bring calm to the daily chaos at the arena and his almost non-existent personal life. A quirky supporting cast surrounds him, including Allison Janney, who plays his boss, Crystal Cohen.
Perry once again shines in a role that plays to his sarcastic, neurotic, and just barely holding-it-all-together strengths. This short-lived series is perfect for fans of workplace comedies or viewers who want to see Perry's neurotic humor in a post-Friends setting. Despite Perry's sharp wit, Mr. Sunshine couldn't match the heart or laughs of the other entries on this list, leaving it in the last spot.
5. 17 Again (2009)
Perry took on a more meaningful comedic role in 17 Again, sharing the character of Mike O'Donnell with Zac Efron. Perry plays the older version of Mike, a man who let life pass him by and finds himself constantly thinking about what could have been. Thanks to a mysterious twist of fate, he wakes up as his 17-year-old self (Efron) and gets a second shot at making things right.
While it might seem like more of an Efron movie, Perry has a weary sort of charm that endears Mike to the audience and gives the story its emotional core. The film will appeal to teen audiences and adults who appreciate lighthearted redemption stories likeNever Been Kissed (1999). Perry's limited screen time makes 17 Again less essential than The Odd Couple, though its message still resonates.
4. The Odd Couple (2015-2017)
Perry stepped into a classic role with The Odd Couple reboot in 2015, playing the famously uptight Oscar Madison opposite Thomas Lennon's neurotic Felix Unger. This modern take on the legendary mismatched roommate sitcom lets Perry flip the dynamic. This time around, Oscar's the messy sportswriter, not the clean freak. As both star and executive producer, Perry put his own stamp on the show, blending his signature comedic timing with a bunch of quirky new antics.
It is a fun, if underrated, run that gave the actor another chance to lead a comedy series. It's perfect for viewers who enjoy sitcoms like Men at Work (2012), which has a similar vibe. While enjoyable, The Odd Couple lacks the same spark Perry brought to Three to Tango, which is why it falls just below in the ranking.
3. Three to Tango (1999)
After being on Friends for a good few years, Perry was cast in a starring role in the 1999 romantic comedy Three to Tango. The story follows Oscar Novak (Perry) and Peter Steinberg (Oliver Platt), who are hired to design a cultural center. Their new boss, Charles Newman (Dylan McDermott), assumes they are a gay couple and asks Oscar to keep his mistress, Amy Post (Neve Campbell), company. But things get complicated when he starts to fall for Amy. The movie is unforgettable thanks to Perry's nervous charm which makes Oscar relatable despite the absurd lie he's caught in.
Perry's comedic timing gives the film a lot of its spark, even when the script gets silly. Though not as polished as The Whole Nine Yards, Perry's boy-next-door warmth shines through, keeping this romantic comedy higher on the list than some of his later projects. It's a great pick for viewers who enjoy quirky, mistaken-identity stories with a charming lead performance like You've Got Mail (1998).
2. The Whole Nine Yards (2000)
The offbeat comedy The Whole Nine Yards is a darkly funny crime caper with Bruce Willis and Amanda Peet. Perry plays Nicholas "Oz" Oseransky, a mild-mannered dentist who is waiting for the day he can afford to divorce his horrible wife. One day, Oz discovers his new neighbor is the infamous hitman Jimmy "The Tulip" Tudeski (Willis). Between mobsters, mistaken identities, and a few unexpected alliances, Oz gets pulled into a world he's definitely not equipped for.
Perry leans into his classic nervous energy in this film, making Oz both likable and hilariously overwhelmed. It's the perfect choice for fans of dark comedy films filled with crime-driven hijinks and witty dialogue like Analyze This (1999). While not as iconic as Friends, Perry's jittery dentist is a pitch-perfect showcase of his comedic timing, proving he can carry a big-screen role with ease.
1. Friends (1994-2004)
Created by David Crane and Marta Kauffman, Friends chronicles the lives of six people as they try to build their lives in New York City. The sitcom's anchor characters are siblings Monica (Courteney Cox) and Ross Geller (David Schwimmer). Their friend group consists of Phoebe Buffay (Lisa Kudrow), Joey Tribbiani (Matt LeBlanc), Rachel Green (Jennifer Aniston), and Chandler Bing (Perry). Each of them has career and relationship dreams of their own. While the cast is legendary, Perry's performance is arguably the linchpin of the show's humor.
His sarcastic delivery, awkward physicality, and surprising vulnerability made Chandler a breakout favorite and cemented Perry's place as one of television's great comedic actors. This timeless sitcom is perfect for anyone who loves witty ensemble comedy, like How I Met Your Mother (2005), and nostalgic '90s vibes. As Perry's defining role, Friends earns the top spot because nothing else quite matches the career-defining brilliance he delivered as Chandler.









































