The 10 Most Underrated Matthew Perry Movies, Ranked (from Least to Most Underrated)

Matthew Perry is remembered first for ‘Friends’, but he built a varied film career that ranges from big-studio comedies to small, character-driven indies and a widely praised teacher biopic made for television. Across these projects he played architects, accountants, explorers, process servers, and educators—often anchoring the story with timing and precision that dovetailed with directors who knew exactly what they wanted from him.

This list spotlights ten screen projects where he took the lead or a pivotal co-lead. Presented as a countdown from ten to one, it spans theatrical releases and television films. Each entry notes who made it, who starred alongside him, and what the story set out to do, so you can quickly place each title in his body of work and decide what you may want to watch next.

‘Serving Sara’ (2002)

Directed by Reginald Hudlin, ‘Serving Sara’ pairs Matthew Perry with Elizabeth Hurley in a New York–set comedy built around process servers, divorce papers, and competing incentives. Perry plays Joe Tyler, whose routine job goes off-course when the target he’s supposed to serve offers him a deal that flips his assignment and sends them on a cross-state chase. The film features supporting turns from Bruce Campbell and Cedric the Entertainer, linking the story’s legal premise with road-movie hijinks and mistaken identities.

Production took advantage of urban locations and highway sequences to stage gags tied to deadlines and contractual fine print. The screenplay uses Joe’s professional tactics—stakeouts, decoys, and timing windows—to set up consecutive set pieces, while Hurley’s character leverages marital law angles to outmaneuver her spouse. The plot’s mechanics revolve around proof-of-service rules, chain-of-custody details, and the incentives that drive the final handoff, keeping the story grounded in the logistics of Joe’s unusual line of work.

‘The Whole Ten Yards’ (2004)

‘The Whole Ten Yards’, directed by Howard Deutch, continues the story launched in ‘The Whole Nine Yards’, reuniting Matthew Perry with Bruce Willis, Amanda Peet, and Natasha Henstridge. Perry returns as mild-mannered dentist Nicholas “Oz” Oseransky, whose suburban cover is tested again when old underworld entanglements resurface. The sequel rebalances the ensemble dynamic by moving characters between hiding places on the U.S.–Mexico border and domestic spaces where identities and motives keep shifting.

The film builds its momentum around impersonations, ransom exchanges, and the logistics of witness protection strategies, with Oz’s clinical precision contrasted against improvisational criminal tactics. Production leans on overlapping schemes that require timed calls, forged documents, and misdirection, allowing Perry’s character to use professional attentiveness to detail—charts, schedules, and contingency planning—inside a plot that treats dentistry and crime as parallel systems of procedure.

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

Written and directed by William Richert from his novel, ‘A Night in the Life of Jimmy Reardon’ is a Chicago-set coming-of-age story starring River Phoenix, with Matthew Perry appearing in a supporting role during the film’s portrait of one eventful night. The narrative follows choices about work, college, and relationships as the lead character tests boundaries before the next stage of life, with period detail placing the action in mid-century neighborhoods and hangouts.

Perry’s presence connects to the film’s ensemble approach, in which each peer represents a different path—family expectations, quick money, or academic ambition. Scenes move through train stations, parties, and diners with conversations that hinge on letters, applications, and deadlines. The adaptation emphasizes how one evening’s decisions can cascade into long-term consequences, using small logistical hurdles—missed connections, borrowed cash, transportation timing—to advance the story beat by beat.

‘Almost Heroes’ (1998)

Directed by Christopher Guest, ‘Almost Heroes’ pairs Matthew Perry with Chris Farley in a frontier expedition comedy that runs parallel to a famous historical trek. Perry plays Leslie Edwards, a high-society would-be explorer who assembles a mismatched team to race toward the Pacific, with Farley’s character providing rough-and-ready counterbalance. The cast includes Eugene Levy and Kevin Dunn, filling out a gallery of guides, rivals, and camp followers.

The film structures its journey around mapmaking, river crossings, supply shortages, and negotiations with traders, giving the travelogue a procedural spine. Production uses location photography to stage set pieces involving natural obstacles and period technology, while the script deploys recurring checklists—provisions, routes, and rendezvous points—to track progress. Perry’s character organizes plans, charts, and terms for the party, anchoring the expedition’s administrative side as the crew confronts hazards and competitive pressure.

‘Three to Tango’ (1999)

‘Three to Tango’, directed by Damon Santostefano, casts Matthew Perry as Oscar Novak, an architect competing for a major commission alongside his business partner, played by Oliver Platt. A mistaken-identity setup involving a wealthy client’s assumptions puts Oscar in frequent contact with the client’s girlfriend, portrayed by Neve Campbell, complicating both the project and the firm’s prospects. Dylan McDermott and John C. McGinley round out the ensemble involved in the development deal.

Architecture pitch sessions, model reviews, and site-visit logistics drive the plot’s beats, with deadlines and stakeholder approvals functioning as story milestones. The film uses voicemail mix-ups, calendar conflicts, and public-relations considerations to escalate the stakes around a single downtown project. Perry’s character moves between drafting tables and boardrooms, navigating procurement steps, nondisclosure constraints, and presentation prep while the mistaken-identity thread intersects with professional obligations.

‘Fools Rush In’ (1997)

Directed by Andy Tennant, ‘Fools Rush In’ brings Matthew Perry together with Salma Hayek in a cross-cultural romance that begins with a chance meeting and grows into a family-focused story. Perry plays Alex Whitman, a New York–based project manager working in Las Vegas, whose relationship with Hayek’s Isabel Fuentes navigates traditions, parents, and long-distance career commitments. The supporting cast includes Tomás Milián and Siobhan Fallon Hogan, tying the couple’s path to both families’ expectations.

The production places emphasis on contrasting settings—Las Vegas development sites and New York offices—while wedding planning, immigration paperwork, and job transfers supply the practical hurdles. Scenes revolve around travel itineraries, religious ceremonies, and housing choices, using tangible tasks to mark each stage of Alex and Isabel’s decisions. The screenplay builds its momentum through concrete steps—meeting relatives, scheduling ultrasounds, aligning holidays—grounding the relationship in everyday logistics.

‘17 Again’ (2009)

Burr Steers directs ‘17 Again’, in which Matthew Perry plays the adult Mike O’Donnell whose life resets when a sudden twist returns him to his teenage body, portrayed by Zac Efron. Leslie Mann and Thomas Lennon co-star in a story that links high-school routines to adult responsibilities, tracking how Mike uses a second pass at classrooms and basketball courts to reassess earlier choices. The narrative cross-cuts between campus activities and family settings to show both timelines’ demands.

School records, tryout rosters, and household schedules structure the plot, with guidance-counselor meetings and court filings establishing procedural steps around education and family law. The film stages set pieces around assemblies, games, and homework deadlines while Mike leverages institutional rules—eligibility, attendance, and parental consent—to steer outcomes. Perry’s scenes bookend the transformation, establishing the before-and-after context that frames the film’s central device.

‘Numb’ (2007)

Written and directed by Harris Goldberg, ‘Numb’ is an independent dramedy centered on a screenwriter whose sudden onset of depersonalization disorder disrupts his life and work. Matthew Perry plays Hudson Milbank, and the film follows his consultations with therapists, trials of medications, and attempts to maintain relationships while navigating symptoms. Lynn Collins and Kevin Pollak appear in key supporting roles tied to Hudson’s creative circle and treatment path.

The production depicts clinical processes—diagnostic interviews, prescription changes, and follow-up assessments—alongside practical writing-room tasks like drafts, notes, and pitch meetings. Scenes incorporate terminology associated with anxiety spectrum conditions and show the stepwise approach to managing them through therapy plans and lifestyle adjustments. The film’s indie framework allows for location-based shooting around offices and modest apartments, using diaries, appointment cards, and script pages as visual anchors for Hudson’s day-to-day routines.

‘The Whole Nine Yards’ (2000)

Directed by Jonathan Lynn, ‘The Whole Nine Yards’ teams Matthew Perry with Bruce Willis in a suburban-crime caper built around a neighbor who turns out to be a notorious hitman. Perry plays Nicholas “Oz” Oseransky, a Montreal dentist whose encounter with new next-door resident Jimmy “The Tulip” Tudeski triggers a chain of favors, payouts, and double-crosses. Amanda Peet, Michael Clarke Duncan, and Natasha Henstridge complete the main ensemble, each tied to competing underworld agendas.

The story’s mechanics rely on contracts, debt ledgers, and jurisdictional boundaries, moving characters between offices, banks, and safe houses. Oz’s dental practice provides a front with appointment books and sterilization cycles that the screenplay uses for timing and cover. Production stages overlapping operations—wire transfers, informant meetings, and extradition risks—so that every scene turns on a concrete task, from swapping identities to coordinating travel across borders.

‘The Ron Clark Story’ (2006)

‘The Ron Clark Story’, directed by Randa Haines, stars Matthew Perry as real-life educator Ron Clark, who relocates to New York City to teach a class with low test scores and high absenteeism. The film follows Clark’s implementation of classroom rules, individualized attention, and after-hours tutoring, mapping policy changes and progress markers across a single academic year. The cast includes Judith Buchan and Ernie Hudson, with students portrayed by a young ensemble whose characters are tracked through attendance and assessment records.

The production details daily school operations—lesson planning, parent outreach logs, and standardized-test preparation—while showing measurable outcomes like practice-test deltas and improvement goals posted on classroom boards. Scenes highlight fundraising steps for materials, field-trip permission processes, and the way behavior contracts are documented and enforced. The film concludes its academic arc by aligning class milestones with district benchmarks, presenting a clear timeline of strategies, interventions, and results.

Share your favorites from this list—and any hidden gems we missed—in the comments!