Essential Rom-Com Movies to Revisit Every Year

Rom-coms mix heart and humor in ways that make them endlessly rewatchable, and the best ones deliver sharp writing, memorable performances, and setups that still work after countless viewings; here’s a friendly refresher on standouts across eras and styles to keep in your yearly rotation.

‘When Harry Met Sally…’ (1989)

Directed by Rob Reiner and written by Nora Ephron, this New York–set story follows two acquaintances whose lives intersect over many years. Billy Crystal and Meg Ryan lead, with Carrie Fisher and Bruno Kirby in key supporting roles. The film popularized witty, observational dialogue about friendship and romance and features multiple interludes of real-couple interviews.

‘Notting Hill’ (1999)

Richard Curtis wrote this London-set romance pairing Hugh Grant as a bookshop owner with Julia Roberts as a film star. Roger Michell directs, with a supporting cast including Rhys Ifans and Emma Chambers. The screenplay plays with fame–meets–ordinary-life dynamics and uses Portobello Road and surrounding neighborhoods for location work.

’10 Things I Hate About You’ (1999)

Gil Junger directs this high-school romance inspired by Shakespeare’s ‘The Taming of the Shrew’. Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, and Larisa Oleynik star. The film was shot around Tacoma and Seattle, with Stadium High School serving as a prominent location.

‘You’ve Got Mail’ (1998)

Nora Ephron directs and co-writes this Upper West Side story about rival bookstore owners who unknowingly connect online. Meg Ryan and Tom Hanks reunite on screen with supporting turns by Greg Kinnear and Parker Posey. It showcases late-90s internet culture and features real New York cafés and shops as backdrops.

‘While You Were Sleeping’ (1995)

Directed by Jon Turteltaub, the film centers on a transit worker who becomes entwined with a Chicago family after a holiday-season misunderstanding. Sandra Bullock, Bill Pullman, and Peter Gallagher star. The story uses Chicago locations—including the ‘L’ train system—to anchor its mistaken-identity premise.

‘Crazy Rich Asians’ (2018)

Jon M. Chu directs this adaptation of Kevin Kwan’s novel, following a New York economics professor who meets her partner’s ultra-wealthy Singaporean family. Constance Wu and Henry Golding star alongside Michelle Yeoh and Awkwafina. The production highlights Singapore and Malaysia locations, lavish production design, and a varied soundtrack.

‘The Big Sick’ (2017)

Based on the real-life courtship of Kumail Nanjiani and Emily V. Gordon, who also co-wrote, this film blends cultural clashes with medical-crisis stakes. Kumail Nanjiani stars with Zoe Kazan, Holly Hunter, and Ray Romano. Michael Showalter directs, and the story foregrounds Pakistani-American family dynamics and stand-up comedy settings.

‘Clueless’ (1995)

Written and directed by Amy Heckerling, this Beverly Hills tale adapts Jane Austen’s ‘Emma’ into a modern high-school world. Alicia Silverstone leads, with Stacey Dash, Brittany Murphy, and Paul Rudd in supporting roles. The film helped popularize distinctive slang, fashion, and a soundtrack tied to its Southern California setting.

‘Bridget Jones’s Diary’ (2001)

Sharon Maguire directs this adaptation of Helen Fielding’s novel about a London publishing professional navigating work, family, and romance. Renée Zellweger stars with Colin Firth and Hugh Grant. The film uses diary narration, well-known London landmarks, and a comedic spin on contemporary dating culture.

‘Four Weddings and a Funeral’ (1994)

Mike Newell directs from a Richard Curtis script following a circle of friends through a series of ceremonies and a chance meeting. Hugh Grant and Andie MacDowell star, with ensemble performances by Kristin Scott Thomas and John Hannah. British countryside churches and reception venues provide the recurring backdrop.

‘Roman Holiday’ (1953)

William Wyler directs this story of a European princess on an incognito day in Rome with an American journalist. Audrey Hepburn and Gregory Peck lead, with a score by Georges Auric. The film showcases Roman landmarks—including the Spanish Steps and the Mouth of Truth—through on-location shooting.

‘The Princess Bride’ (1987)

Rob Reiner directs this fairy-tale adventure adapted by William Goldman from his own novel, blending romance, swordplay, and satire. Cary Elwes and Robin Wright star, with Mandy Patinkin and Wallace Shawn delivering memorable roles. The production mixes studio work with countryside locations and features music by Mark Knopfler.

‘Groundhog Day’ (1993)

Harold Ramis directs this time-loop comedy about a TV weatherman reliving the same small-town day. Bill Murray and Andie MacDowell star, with shooting centered in Woodstock, Illinois, standing in for Punxsutawney. The narrative structure uses repeated scenarios to explore character change within a romantic framework.

’13 Going on 30′ (2004)

Directed by Gary Winick, this body-swap comedy follows a teen who wakes up in her future adult life in New York media. Jennifer Garner and Mark Ruffalo star, with Judy Greer in a key supporting role. The story uses magazine publishing workplaces and classic pop tracks to frame its romantic throughline.

‘How to Lose a Guy in 10 Days’ (2003)

Donald Petrie directs this magazine-assignment-meets-marketing-bet premise set in Manhattan. Kate Hudson and Matthew McConaughey star, with Bebe Neuwirth and Kathryn Hahn in supporting roles. The film incorporates fashion, advertising pitches, and upscale New York locales to drive its cat-and-mouse setups.

‘My Best Friend’s Wedding’ (1997)

P. J. Hogan directs this Chicago-and-Baltimore-set story about a food critic confronting long-buried feelings when her best friend gets engaged. Julia Roberts, Dermot Mulroney, Cameron Diaz, and Rupert Everett lead the ensemble. Musical set-pieces and newsroom scenes anchor the romantic complications.

‘Pretty Woman’ (1990)

Garry Marshall directs this Beverly Hills–set romance between a businessman and a spirited escort. Julia Roberts and Richard Gere star, with Hector Elizondo and Laura San Giacomo in supporting roles. The film features Rodeo Drive shopping sequences, luxury-hotel settings, and a soundtrack closely associated with its story.

‘Amélie’ (2001)

Jean-Pierre Jeunet writes and directs this whimsical Paris-set tale about a shy waitress who orchestrates small acts that transform lives. Audrey Tautou stars, with a score by Yann Tiersen. The production uses Montmartre locations, stylized color grading, and playful visual effects to frame its romantic thread.

‘Silver Linings Playbook’ (2012)

David O. Russell adapts Matthew Quick’s novel about two people rebuilding after personal and family upheaval. Bradley Cooper and Jennifer Lawrence star, with Robert De Niro and Jacki Weaver in supporting roles. The film integrates mental-health themes, suburban Philadelphia settings, and a dance-competition finale into its romance.

‘Love Actually’ (2003)

Written and directed by Richard Curtis, this ensemble piece interweaves multiple love stories across London during the holiday season. The cast includes Hugh Grant, Emma Thompson, Keira Knightley, Bill Nighy, and more. Interlocking narratives, airport sequences, and recognizable city landmarks bind the threads.

‘The Holiday’ (2006)

Nancy Meyers writes and directs this home-exchange romance set between Los Angeles and the English countryside. Cameron Diaz, Kate Winslet, Jude Law, and Jack Black star. Distinct production design highlights cozy cottages and modern SoCal homes, with film-industry touches woven into the Los Angeles storyline.

‘To All the Boys I’ve Loved Before’ (2018)

Based on Jenny Han’s novel, this teen-focused rom-com follows a high-schooler whose private letters spark an unexpected relationship. Lana Condor and Noah Centineo star, with Susan Johnson directing. The film showcases Pacific Northwest locations and launched a successful streaming franchise.

‘Always Be My Maybe’ (2019)

Directed by Nahnatchka Khan, this San Francisco–set story reunites childhood friends on diverging life paths. Ali Wong and Randall Park star, with supporting appearances by Daniel Dae Kim and others. The film integrates food-culture details, music connections, and a notable celebrity cameo.

‘Palm Springs’ (2020)

Max Barbakow directs this time-loop romance set around a desert wedding. Andy Samberg and Cristin Milioti star, with J. K. Simmons in a pivotal role. The production uses Coachella Valley locations and blends sci-fi mechanics with wedding-weekend hijinks to shape its love story.

‘Moonstruck’ (1987)

Directed by Norman Jewison, this Brooklyn-set romance centers on a bookkeeper who falls for her fiancé’s brother. Cher and Nicolas Cage lead, with Olympia Dukakis and Vincent Gardenia in the ensemble. The film features Italian-American family dynamics, opera motifs tied to the Met, and neighborhood restaurant scenes.

‘Sleepless in Seattle’ (1993)

Directed by Nora Ephron, this coast-to-coast romance connects a widower in Seattle with a journalist in Baltimore. Tom Hanks and Meg Ryan lead, with supporting turns by Bill Pullman and Rosie O’Donnell. The film references classic cinema, uses radio call-in framing, and culminates at a landmark New York skyscraper.

‘Crazy, Stupid, Love.’ (2011)

Glenn Ficarra and John Requa direct this interwoven story about a recently single father mentored by a charismatic bachelor. Steve Carell, Ryan Gosling, Julianne Moore, and Emma Stone headline the ensemble. The film balances converging subplots, bar-lesson montage sequences, and a school event set-piece.

‘The Proposal’ (2009)

Anne Fletcher directs this immigration-paperwork premise pairing a high-powered editor with her assistant on a trip to Alaska. Sandra Bullock and Ryan Reynolds star, with Betty White in a featured role. The production contrasts Manhattan offices with small-town settings and uses workplace dynamics to kickstart the arrangement.

‘Hitch’ (2005)

Directed by Andy Tennant, the story follows a professional dating consultant navigating his toughest client and his own match. Will Smith, Eva Mendes, Kevin James, and Amber Valletta star. The New York City backdrop includes harbor scenes, gallery events, and dance-floor comedy tied to character coaching.

‘About Time’ (2013)

Richard Curtis writes and directs this time-travel romance centered on a family secret that lets the protagonist revisit moments in his life. Domhnall Gleeson, Rachel McAdams, and Bill Nighy lead the cast. London and Cornwall locations, a wedding sequence, and recurring father–son conversations structure the narrative.

‘My Big Fat Greek Wedding’ (2002)

Nia Vardalos writes and stars in this culture-clash romance about a Chicago woman balancing family traditions with a new relationship. John Corbett co-stars, with Andrea Martin, Michael Constantine, and Lainie Kazan in the ensemble. The film originated from a one-woman stage show and became a major independent-film success.

‘Jerry Maguire’ (1996)

Cameron Crowe directs this sports-agency romance that tracks a fired agent rebuilding his career with a single client and a new partner. Tom Cruise, Renée Zellweger, and Cuba Gooding Jr. star. The story features agency politics, road-game travel, and a contract-negotiation arc that intersects with family life.

‘The Wedding Singer’ (1998)

Frank Coraci directs this music-infused romance set in suburban New Jersey. Adam Sandler and Drew Barrymore star, with scenes built around banquet halls, roller rinks, and live-band performances. The soundtrack leans on pop hits, and the plot uses event-planning mishaps to drive character turns.

‘Enchanted’ (2007)

Directed by Kevin Lima, this hybrid live-action and animation story transports a fairy-tale heroine into modern Manhattan. Amy Adams, Patrick Dempsey, James Marsden, and Idina Menzel star, with original songs by Alan Menken and Stephen Schwartz. The film stages musical numbers in city locations, including a large-scale park sequence.

‘The Shop Around the Corner’ (1940)

Ernst Lubitsch directs this Budapest-set story about co-workers who unknowingly correspond as anonymous pen pals. James Stewart and Margaret Sullavan lead, supported by a tight ensemble in a leather-goods store setting. The script uses letter exchanges, workplace rivalries, and holiday retail pressure to reveal identities.

‘His Girl Friday’ (1940)

Howard Hawks directs this rapid-fire newsroom comedy centered on an editor trying to win back his star reporter. Cary Grant and Rosalind Russell headline, with overlapping dialogue and press-room antics shaping the pace. The plot weaves a breaking crime story, political angles, and professional rivalry into its romantic thread.

‘The Philadelphia Story’ (1940)

Directed by George Cukor, this high-society romance follows a socialite whose wedding weekend is upended by the arrival of her ex-husband and a reporter. Katharine Hepburn, Cary Grant, and James Stewart star. Mansions, poolside gatherings, and magazine-assignment setups frame the misunderstandings and shifting loyalties.

‘It Happened One Night’ (1934)

Frank Capra directs this cross-country road romance between a runaway heiress and a reporter. Clark Gable and Claudette Colbert star, with bus stations, auto camps, and roadside inns providing the itinerary. The screenplay mixes travel obstacles with press deadlines and identity concealment.

‘Annie Hall’ (1977)

This New York–centered romance uses non-linear structure, direct address, and stylized vignettes to chart a relationship from meeting to aftermath. Diane Keaton and Woody Allen star, with appearances by Carol Kane and Paul Simon. City streets, comedy clubs, and apartment interiors anchor the character-driven scenes.

‘Set It Up’ (2018)

Claire Scanlon directs this workplace-mischief romance about two overworked assistants engineering a match between their demanding bosses. Zoey Deutch and Glen Powell star, with Lucy Liu and Taye Diggs as the executives. The story uses office towers, late-night food runs, and stadium interludes to escalate the scheme.

Share your go-to rewatch from this expanded list in the comments and tell us which rom-coms you think deserve a spot next time!