Highlights

• Matthew Perry's film "17 Again" was his highest-grossing movie, earning $139 million at the box office.
• "The Whole Nine Yards" was a box office hit, making $106 million and turning a profit of over $64 million.
• Despite its comedic appeal, "Almost Heroes" struggled at the box office and resulted in a financial loss.

The late Matthew Perry has a name synonymous with wit and uproarious humor.

Perry garnered fame through his ever-iconic portrayal of Chandler Bing on the beloved television series Friends. The talented actor was born in Williamstown, Massachusetts, and embarked on his Hollywood journey at a very young age; his first credited role was a small part in the television show 240-Robert as a child actor in 1979.

While Chandler Bing and Friends made Perry a household name, his success extended beyond the realm of sitcoms. Alongside his acting career, he ventured into producing, voicing, acting, and writing.

In 2022, he published his memoir Friends, Lovers, And The Big Terrible Thing, which details his adventure in Hollywood and his love life.

Due to his remarkable talent, skill, and on-screen chemistry with his co-stars, Perry has had his share of success in numerous movies, some of which have achieved significant box office results, such as 17 Again and Serving Sara.

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9 Almost Heroes

Almost Heroes is a 1998 western comedy film directed by Christoper Guest and narrated by Harry Shearer. It tells the story of two inept aristocrats, Leslie Edwards and Bartholomew Hunt.

Matthew Perry plays Leslie Edwards, a mild-mannered and clumsy explorer on a quest to beat Lewis and Clark in the race to be the first to chart and make it across the United States to the Pacific Ocean. The movie had a reported production budget of $30 million.

Unfortunately, Almost Heroes struggled at the box office, grossing around $6.1 million and resulting in a financial loss. Despite its comedic appeal and Perry's memorable performance, critical reception of the movie was generally negative.

8 A Night In The Life Of Jimmy Reardon

A Night in the Life of Jimmy Reardon is a coming-of-age drama film written and directed by William Richert. Released in 1988, the movie features a young Matthew Perry as he makes his film debut.

Perry portrays the character of Fred Roberts, a close friend of the titular character, Jimmy Reardon, played by the late River Phoenix. A Night in the Life of Jimmy Reardon had a relatively modest budget, estimated at around $5 million.

However, it could have done better at the box office as it only grossed $6,175,688. The movie would later grow on cinema goers thanks to the budding talent and the chemistry between Phoenix and Perry, who became friends after the movie.

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

7 Three To Tango

Three to Tango is a rom-com starring Matthew Perry in a leading role, alongside Neve Campbell and Dylan McDermott.

The plot tells the story of Oscar Novak (Perry's character), an architect who becomes embroiled in a comedic misunderstanding when he is mistaken for a gay man by his wealthy client, who employs him to spy on his mistress, Amy. The movie made $10.5 million domestically against a budget of $20 million, registering a loss of over $9 million.

Despite the star-studded cast and humorous premise, the film received much criticism for its offensive humor and lack of originality in the script. Matthew Perry's character was praised, however, for his versatility and upbeat humor.

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6 She's Out Of Control

Another of Perry's early roles, She's Out Of Control, is an independent coming-of-age comedy film. The movie revolves around a father's struggle with his teenage daughter's newfound popularity and romantic interests.

Perry played the role of Timothy, the main character's love interest. Produced on a budget of $12 million, She's Out of Control broke even at the box office, grossing exactly $12 million.

The film unfortunately failed to live up to its potential, and critics slammed it for its lack of substance. But certainly, the underrated comedy had its own fun that Matthew Perry's fans can enjoy.

5 Serving Sara

This 2002 romantic comedy from Reginald Hudlin perfectly reminded the audience of Matthew Perry's undiluted comedic chops. Serving Sara features Perry in a supporting role as Joe Tyler, a process server tasked with delivering divorce papers to the titular character, Sara Moore, played by Elizabeth Hurley.

However, when Sara offers Joe a financial incentive to serve her husband first, the two embark on a trip across the country, and a comedic journey unfolds. The movie faced challenges at the box office; it recorded a loss of $9 million after it turned in $20 million on a budget of $29 million.

4 The Whole Ten Yards

The Whole Ten Yards is a 2004 crime comedy directed by Jonathan Lynn, and it is a sequel to the 2000 film TheWhole Nine Yards. Perry's physical comedy is unmatched in this thriller.

He reprises the role of Nicholas "Oz" Oseransky from the first movie as he teams up with hitman Jimmy (played by Bruce Willis) to rescue Oz's wife. Unlike the first film, which was a commercial success, The Whole Ten Yards was a box office bomb, bringing in only $16.3 million in North America and $9.8 million internationally.

Despite the return of the original cast, the sequel failed to match the success of its predecessor and faced challenges in achieving profitability. With a worldwide total of $26 million, the film did not recoup its $40 million budget.

3 Fools Rush In

Matthew Perry starred alongside Salma Hayek in Andy Tennant's romantic comedy Fools Rush In. The movie follows the characters of Hayek and Perry as they attempt to turn their one-night stand experience into a marriage after Hayek's character discovers that she is pregnant.

Matthew Perry's father, John Benneth Perry, also portrayed his character's father in the movie. The movie had a production budget estimated at $20 million.

Fools Rush In fared well at the box office, grossing $29.5 million domestically and $13 million in other territories for a worldwide total of $42 million.

2 The Whole Nine Yards

The Whole Nine Yards is a crime comedy film released in 2000, with Matthew Perry taking on the role of Nicholas "Oz" Oseransky, a beleaguered dentist who becomes embroiled in the schemes of a notorious hitman Jimmy "The Tulip" Tudeski, played by Bruce Willis.

The Whole Nine Yards was an instant hit at the box office, raking in $13 million in its opening weekend and $9.6 million in its second weekend. The film grossed $106 million at the box office.

After its run in theaters, The Whole Nine Yards registered a profit of over $64 million from a budget of $41 million. The film's clever blend of dark humor and crime elements, along with the chemistry between Perry and Willis, contributed to its box office triumph.

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1 17 Again

17 Again was Matthew Perry's last film, and fittingly, it became his highest grossing movie. Perry starred alongside Zac Efron in this teen fantasy comedy directed by Burr Steers and released in 2009.

Perry's last film role found him going back to the teen genre that gave him his start, with a dash of fantasy in the story. Perry portrays the character of Mike O'Donnell, a man who magically transforms into his 17-year-old self, played by Zac Efron, and relives his high school years.

17 Again grossed $139 million at the box office on the back of a $40 million budget, making it a massively profitable venture and a significant milestone in Matthew Perry's film career.