Top 10 Memorable Matthew Perry Movie Roles
#10: Fred Roberts “A Night in the Life of Jimmy Reardon” (1988)
The late River Phoenix headlined this coming-of-age drama as the titular Jimmy Reardon, but it also marked Perry’s film debut. Perry plays Fred, a wisecracker who’s constantly loaning his best friend money, can be awkward around the ladies, and knows how to rock a vest. Even six years before Chandler Bing, Perry was planting the seeds for that character. As Fred, Perry brings what would become his signature sarcasm to the role, scoring some of the film’s wittiest one-liners despite not having the most screen time. Although Fred breaks things off with the selfish Jimmy, Perry developed a genuine friendship with Phoenix on set. Making this film, Perry wrote that he “fell deeply in love with acting,” helping to solidify his career path.
#9: Joe Tyler “Serving Sara” (2002)
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In his memoir, Perry revealed that he wasn’t especially proud of “Serving Sara,” which halted production during his stay in rehab. Perry’s struggles were apparent to co-star Elizabeth Hurley, who reflected, “He was still very charming and a lovely person to work with. But you could see he was suffering for sure.” While not a masterpiece, we have a soft spot for this road trip romcom primarily because its leads are so well-cast. Perry as a cynical process server is a natural fit while Hurley delights as a spoiled yet street-smart socialite. Although even Joe acknowledges that he’s a loser, Perry infuses the role with such endearing energy that we can’t help but root for him. He’s one process server we looked forward to seeing.
#8: Morrie Tanager “Birds of America” (2008)
Although Perry became known for his comedic chops, he was underrated as a dramatic talent. In this Sundance dramedy, Perry leans into his serious side as Morrie, a college professor who’s spent most of his life taking care of his dysfunctional younger siblings. This holds Morrie back from starting a family with his wife, pushing his patience to the edge of reason. With each line delivery from Perry, the audience can sense Morrie’s frustration, but also the responsibility that he has for his siblings’ well-being. Perry makes us feel for this guy, who’s trying his best to keep his family together. On the inside, though, he’s barely keeping himself in one piece. Morrie is a reluctant father figure, but he’s there for his family nonetheless.
#7: Hudson Milbank “Numb” (2007)
The romcom genre suited Perry like a glove, but “Numb” stands out as one of the most unique examples from his filmography. Inspired by writer/director Harris Goldberg’s experiences living with depersonalization disorder, the film stars Perry as a screenwriter who becomes withdrawn from the rest of the world. Upon receiving his diagnosis, Perry’s Hudson attempts to connect with others, although he’s often at odds with himself. Perry delivers one of his most physically impressive performances as a man who feels as if he’s not living in his own skin. Despite Hudson’s detachment, we can still sense his desire to form a meaningful bond. Before he does that, though, Hudson must accept himself. Goldberg was proud of Perry’s performance, calling him his Gregory Peck.
#6: Oscar Novak “Three to Tango” (1999)
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As the title suggests, this rom-com centers on a love triangle with Perry’s Oscar caught in the middle. Oscar is head over heels for Neve Campbell’s Amy, who’s involved with his boss, played by Dylan McDermott. Making matters more complicated, both think that Oscar is gay, snowballing into a lie that spirals out of control. Although the setup makes for some jokes that haven’t aged well, the script’s shortcomings are elevated by the first-rate cast. Campbell is a quintessential girl next door while Perry summons empathy for a character who could come off as problematic, but ultimately learns to be more honest with others and himself. Perry and Campbell briefly dated during shooting, which shines through in their on-screen chemistry.
#5: Leslie Edwards “Almost Heroes” (1998)
A cloud of sadness loomed over this comedy’s premiere, coming out six months after Chris Farley tragically died. Watching the film now, it’s hard not to think about how Farley and Perry were both taken from us far too soon. At the same time, we’re grateful for the work that these two comedy legends left behind. “Almost Heroes” is no exception. The two make for a fun odd couple with Farley as a brash tracker and Perry as a nobleman who underestimates the unpredictable nature of… well, nature. Leslie Edwards is among Perry’s most eccentric characters, taking on the wildness with a mix of ambition and naive optimism. They’re not Lewis and Clark, but that’s why Perry and Farley are such a memorable duo.
#4: Older Mike O’Donnell “17 Again” (2009)
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Zac Efron isn’t the spitting image of a young Matthew Perry. And yet, we’re willing to accept them as the same person because both are such fun to watch in this teen comedy. Perry plays the middle-aged Mike, who’s out of a job while his marriage collapses. Suddenly transformed into his 17-year-old self, Mike is initially more interested in reliving the glory days and pursuing the roads not taken. Instead, he comes to value the life that he walked away from, attempting to salvage his future. Although Efron gets more screen time, Perry brings the film full circle as Mike comes to realize what’s most important in life. It’s a juggling act of cynicism and sincerity that Perry is more than capable of pulling off.
#3: Alex Whitman “Fools Rush In” (1997)
A decade before we got several movies about unplanned pregnancies, “Fools Rush In” proved to be ahead of the curve. Perry plays Alex, whose one-night stand with Salma Hayek’s Isabel becomes long-term following an unexpected discovery. A more conventional film would focus on Alex coming to terms with commitment. To Isabel’s surprise, Alex is quick to propose. The leads share such instantaneous chemistry that it’s easy to believe their accelerated relationship. Since marriage came first, though, Alex and Isabel must work backward as they learn about each other’s families and desires. Calling this “probably [his] best movie,” Perry gives one of his most mature performances as a man trying to balance the life he always wanted and the one he never knew he wanted.
#2: Ron Clark “The Ron Clark Story” (2006)
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Perry leads this TV movie as Ron Clark, a teacher who’d touch the lives of numerous students that the system had already given up on. While the script has a few witty one-liners, Perry otherwise gets to play against type in one of his most dramatic roles. He shines as an inspirational educator who unifies the classroom with a blend of humor, understanding, and tough love when it’s necessary. The film isn’t a complete portrait of Clark’s life, notably giving him a female love interest when in reality, he’s openly gay. The real Clark was still a big fan of the film, calling it “beautiful.” It’d be among Perry’s most acclaimed performances, earning him nominations at the Primetime Emmys, SAG Awards, and Golden Globes.
#1: Nicholas “Oz” Oseransky “The Whole Nine Yards” (2000)
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Perry excelled at playing average guys who find themselves surrounded by colorful characters. No film better reflected this than “The Whole Nine Yards,” as Perry’s Oz winds up caught between the woman he loves, the wife he loathes, and several killers, one played by Bruce Willis. While Oz is the voice of reason, he’s not a stick in the mud thanks to Perry, who offsets the insanity with quick-witted delivery. He reunited with Willis for a sequel, a few “Friends” episodes, and “Disney’s The Kid” where Perry had an unrecognizable cameo. Yet, this dark comedy is the sharpest testament to their chemistry, as well as Perry’s potential as a movie star. Funny, sympathetic, and full of charm, Perry indeed goes the whole nine yards. What’s your favorite Matthew Perry movie role? Let’s fondly remember the actor in the comments.
