Remembering Matthew Perry's best movie roles, from ‘Fools Rush In’ to ‘17 Again’

Matthew Perry, who died at age 54 on Oct. 28, leaves behind a decades-long legacy in Hollywood.

Perry may be best known for his role as Chandler Bing on the TV series “Friends,” but he also starred in several other sitcoms over the years, including “Mr. Sunshine,” “Go On,” and “The Odd Couple.”

And beyond his sprawling career of roles and guest spots on television, Perry also had a career on the silver screen, beginning with “A Night in the Life of Jimmy Reardon” in 1988. He went on to star in a variety of films, ranging from drama and rom-coms to comedy and adventure.

Here, we remember Matthew Perry with a look at some of his best movies through the years.

‘A Night in the Life of Jimmy Reardon’ (1988)

Perry appeared alongside River Phoenix, Meredith Salenger, and Ione Sky in the 1988 drama “A Night in the Life of Jimmy Reardon.”

The movie follows Phoenix’s character, Jimmy Reardon, as he decides what to do after finishing high school. Rather than pursuing the same path as his father and going to business school, he gets a job to try to earn himself money to get a plane ticket to Hawaii.

In the movie, based on the book “Aren’t You Even Gonna Kiss Me Goodbye?” by William Richert, Perry portrays the character Fred Roberts, the affluent best friend of Phoenix’s character.

Perry reflected on the production of the movie in his memoir, “Friends, Lovers, and the Big Terrible Thing,” writing that he had “never been so excited” in his life.

“It was in Chicago, and on this movie, and with River Phoenix, that I fell deeply in love with acting — and the cherry on top of this deeply magical time was that River and I became firm friends,” he wrote. “He and I drank beer and shot pool on North Rush Street.”

Though the movie ultimately did not do well and Phoenix tragically died of an overdose in 1993, Perry looked back fondly on the filming of the movie.

“When it came to the last day of shooting, I sat on my bed in my room and cried,” he wrote. “I sobbed and sobbed because I knew even then I would never again have an experience like that — my first movie, far from home, free to flirt and drink and hang out with a brilliant young man like River Phoenix.”

‘Fools Rush In’ (1997)

Perry starred in the rom-com “Fools Rush In” opposite Salma Hayek in 1997. The actor’s father, John Bennett Perry, also portrayed his character’s father in the movie.

The movie follows Hayek’s character, Isabel Fuentes, three months after a one-night stand in Las Vegas with Perry’s character, Alex Whitman. Isabel discovers that she is pregnant and — despite living a bachelor lifestyle as a real estate developer in New York City — Alex and Isabel get married, much to the dismay of her father.

Throughout the film, Alex has to decide whether he will return to New York after he is offered a promotion, or continue with his new life in Las Vegas.

In his memoir, Perry looked back fondly on the film, saying it was “probably my best movie.” He called director Andy Tennant “a very smart and incredibly nice guy” who offered him advice on set that improved his performance.

“I was bouncing around doing my funny little things, and [Tennant] would take me aside and say, ‘You don’t have to do that. You’re interesting enough to watch without doing that,’” Perry wrote. “That line of thinking allowed him to pull out of me one of the best performances of my career. Could this be a different way of saying 'Matty, you’re enough, the words I’ve been longing to hear my entire life?'”

‘Almost Heroes’ (1998)

Perry alongside Chris Farley and Eugene Levy starred in 1998’s comedy-adventure “Almost Heroes.”

The movie followed Leslie Edwards (Perry) and Bartholomew Hunt (Farley), two explorers who are racing Lewis and Clark to reach the Pacific Ocean in 1804. As they make their trek through America, they meet a cast of interesting characters and create chaos in their wake.

“Almost Heroes” marked the last leading film role for Farley, who died in 1997 on Dec. 18. The movie was released posthumously — and just two weeks after Farley's death, Perry had to promote the film, a moment he reflected on in his memoir.

“Then, Chris Farley died... I punched a hole through Jennifer Aniston’s dressing room when I found out,” he wrote. “I had to promote 'Almost Heroes' two weeks after he died; I found myself publicly discussing his death from drugs and alcohol. I was high the entire time.”

‘Three To Tango’ (1999)

Perry made his return to rom-coms with 1999’s “Three to Tango,” starring Neve Campbell, Dylan McDermott, and Oliver Platt.

The film follows Perry’s character Oscar and Platt’s character Peter when they are chosen by McDermott’s character to compete to design a cultural center. However, McDermott’s character mistakes Perry’s character's sexuality and has him spy on his mistress, Amy, portrayed by Neve Campbell. Oscar goes along with the ruse, but ultimately falls for Amy.

‘The Whole Nine Yards’ (2000)

Perry alongside Bruce Willis, Amanda Peet, Michael Clarke Duncan, and Rosanna Arquette starred in 2000’s crime comedy “The Whole Nine Yards.”

In the movie, Willis’ character, hitman Jimmy “The Tulip” Tudeski moves into a nice suburb. However, his arrival sets off a chain of events. Perry plays dentist Nicholas “Oz” Oseransky, Jimmy’s next door neighbor who ends up on both his good and his bad side.

Perry wrote about his relationship with Willis on the set of the film in his memoir, sharing some of the touching moments between the actors behind-the-scenes.

“Sometimes, at the end of the night, when the sun was just about to come up and everyone else had gone, and the party was over, Bruce and I would just sit and talk,” he wrote. “That’s when I saw the real Bruce Willis — a good-hearted man, a caring man, selfless. A wonderful parent. And a wonderful actor. And most important, a good guy.”

He added, “And if he wanted me to be, I would be his friend for life. But as is the way with so many of these things, our paths rarely crossed after that. I, of course, pray for him every night now.”

‘Serving Sara’ (2002)

Perry and Elizabeth Hurley played love interests in 2002’s “Serving Sara,” which also featured Bruce Campbell, Cedric the Entertainer, and Terry Crews.

The romantic comedy follows Hurley’s character, Sara, after she is served divorced papers while she is in New York. Determined to not lose the large sum of money from her husband, Gordon (Campbell), she makes a proposition to her process server, Joe (Perry), and the two embark on a trip across the country.

After the release of his memoir, Hurley opened up to Yahoo Entertainment about the behind-the-scenes of working with Perry on the movie when the set of the film was shut down for two months due to his struggles with addiction.

“I have very fond memories of him,” she said. “To be honest, it was a nightmare working with him at that time and, as it’s now known, our movie was shut down because of his addiction. We were in a force majeure and had to all sit at home twiddling our thumbs for some time.”

In the book, he acknowledged that his addictions affected the production of the movie, writing that his co-star Hurley as well as director Reginald Hudlin were “pissed off” because Perry had “ruined his movie.”

‘The Whole Ten Yards’ (2004)

Perry, Willis, and Peet returned for a sequel to 2000’s “The Whole Nine Yards” with “The Whole Ten Yards” in 2004.

The movie follows former hitman Jimmy Tudeski after he retires in Mexico with his new wife, Jill (Peet). Back in California, Jimmy’s ex-wife Cynthia (Natasha Henstridge) settles down with Nicholas. However, their peaceful lives are disrupted when a member of the Hungarian Mafia, Janni Gogolak (Kevin Pollak), gets revenge by kidnapping Cynthia.

In her tribute to Perry, Rumer Willis reflected on her time as a child on set with her father for both movies.

“I’m so sad to hear about Matthew Perry passing,” she wrote on her Instagram story. “When I was a kid and I was on Set while he and my dad were doing whole nine and whole 10 yards he was so kind and funny and sweet with my sister and me and I think his physical Comedy and that movie still makes me laugh so much.”

‘The Ron Clark Story’ (2006)

Perry, Hannah Hudson, Brandon Mychal Smith, Melissa De Sousa, and Ernie Hudson starred in the 2006 drama “The Ron Clark Story.”

The movie follows Ron Clark (Perry), an elementary school teacher in his hometown in North Carolina. Despite his comfortable life, he follows his calling and moves to New York City in hopes of helping students in the struggling school system.

‘Numb’ (2007)

Perry continued his dramatic streak with “Numb” in 2007, also starring Mary Steenburgen, Lynn Collins, and his “The Whole Ten Yards” co-star, Pollak.

In the movie, Perry portrays successful screenwriter Hudson Milbank. All of a sudden, Hudson experiences no emotions, which he tries to solve with several doctors and mental health professionals.

‘Birds of America’ (2008)

In a star-studded cast, Lauren Graham, Hilary Swank, Ben Foster, Ginnifer Goodwin, and Zoë Kravitz starred in the 2008 indie drama “Birds of America.”

In “Birds of America,” Perry’s character Morrie Tanager helped raise his brother and sister, Jay (Foster) and Ida (Goodwin). Morrie’s wife Betty (Graham) wants to start a family, but when Jay and Ida need a place to stay and show up at Morrie’s home, he finds himself caring for his siblings again.

‘17 Again’ (2009)

In one of his last film roles, Perry starred in 2009’s “17 Again” alongside Zac Efron, Leslie Mann, Michelle Trachtenberg, Sterling Knight, and his “The Odd Couple” co-star, Thomas Lennon.

When he was in high school, Perry’s character Mike O’Donnell was a basketball star who was destined to do big things. However, he pushed aside his dreams to marry his girlfriend, Scarlet (Mann) so they could raise their child. In the future, Mike’s marriage is struggling, and his relationship with his two kids Maggie (Trachtenberg) and Alex (Knight) is fraught at best.

Mike is given the opportunity to change his past and is transformed back into his teenage self as a 17-year-old, as portrayed by Efron — but he puts his future at risk.

This article was originally published on TODAY.com