The 50 Best R-rated Rom-Coms of the Past 50 Years

Vince Vaughn and Owen Wilson are two divorce mediators who in their spare time crash weddings. But they get more than they bargained for when they end up at the wedding of the daughter of a presidential hopeful (played by Christopher Walken). Rachel McAdams and Isla Fisher are the girls they meet at the wedding. Bradley Cooper makes an early-career appearance in the movie.

Emily Blunt plays Iris, who invites her friend Jack (Mark Duplass) to stay at her family’s island getaway after his brother has passed away. Iris’s sister Hannah, getting over a long-term relationship, has a drunken affair with Jack, creating a complicated situation for Iris.

Donal Logue plays Dex, once a real ladies’ man in college, who has become an overweight kindergarten teacher. He’s about to attend his college reunion and meet the women he once romanced.

The puerile humor in Robert and Peter Farrelly (who can forget the “gel” the title character puts in her hair) is leavened by the film’s inherent sweetness, attributable to the charms of the cast.

Cédric Klapisch directed and wrote this breezy rom-com, the third installment of his “Spanish Apartment” trilogy. It concerns a 40-year-old divorced man who can’t cope with the thought of his children moving to New York from France with their mother – so he decides to move there also.

Lake Bell stars as a woman who is mistaken for a man’s blind date and decides to go ahead with the rendezvous anyway. Critics said the chemistry between Bell and Simon Pegg, who plays the man, made this rom-com work.

Rom-com meets sci-fi in this film starring Vincent D’Onofrio as a time traveler in contemporary New York City who meets Marisa Tomei – a woman who has an understandably hard time dealing with the fact her first healthy relationship is with someone from another era.

“Adventureland” is about a recent college graduate (Jesse Eisenberg) whose dreams of a summer in Europe are put on hold because his parents tell him they can’t afford to pay for the trip. He takes a job at an amusement park and instead of enduring his worst summer ever, he falls in love with a beautiful co-worker (Kristen Stewart). Greg Mottola wrote and directed the critically favored rom-com.

Very much a film of its time, “Valley Girl” is an early-career starring vehicle for Nicolas Cage, appearing as a Hollywood punk who romances Deborah Foreman, a girl from the San Fernando Valley whose friends are materialistic, narcissistic teens.

“Working Girl” is a very 1980s movie; the go-go financial world and the high hair are giveaways. Melanie Griffith plays a secretary who takes advantage of her domineering boss’s absence by presenting a potentially profitable idea – which the boss then tries to take credit for. The supporting cast in this rom-com directed by Mike Nichols includes Sigourney Weaver, Joan Cusack, Alec Baldwin, and Philip Bosco.

“Conversations with Other Women” is a rom-com drama about former lovers (Helena Bonham Carter and Aaron Eckhart), unnamed in the movie, who reconnect at a wedding and discover their mutual attraction has not waned. Critics noted the charisma of the two lead characters as the film’s strong suit.

Total strangers Peter (Charlie Day) and Emma (Jenny Slate) meet after getting dumped by their respective partners. They find out via social media that both of their exes have moved on to other relationships and decide to try to get them back.

This quirky rom-com paired Seth Rogen and Charlize Theron as a journalist and politician, respectively. He realizes she was his babysitter and childhood crush. Things become even more interesting when she hires him as her speechwriter in her bid for the presidency, much to the chagrin of her advisers.

Mark Ruffalo earned critics’ kudos for his portrayal of a man with chronic depression issues who becomes a stay-at-home dad for his two precocious daughters while his wife (Zoe Saldaña) pursues an MBA to get a job that can support the family.

A rom-com/fantasy directed by Yorgos Lanthimos, “The Lobster” stars Colin Farrell and Rachel Weisz in a film about a dystopian society in which single people must find a mate within 45 days or be transformed into an animal of their choice. Mark Harris of Grantland said the movie was a “brilliant black comedy so steeped in loneliness it could break your heart if you let it.”

Michael Showalter directed and co-wrote this rom-com starring Sally Field as an older office worker encouraged by her best friend’s social-media-savvy granddaughter to meet the granddaughter’s much younger coworker (Max Greenfield).

Jorge Furtado directed and wrote this Brazilian import about a photocopier operator (Lázaro Ramos) smitten by a neighboring girl who doesn’t know he exists. As he dreams of becoming a cartoonist, he uses his photocopying skills to make counterfeit money.

In one of the roles that vaulted Renée Zellweger into fame, she stars as career woman Bridget Jones, who is looking for Mr. Right. She has to choose between her somewhat caddish but attractive boss (Hugh Grant) and a more decent fellow (Colin Firth).

“Something Wild,” directed by Jonathan Demme, starred Melanie Griffith as a free-spirited young woman who hooks up with buttoned-up banker (Jeff Daniels) for a wild fling. Things begin to go off the rails when her ex-convict husband (Ray Liotta) shows up. The movie included cameos by directors John Sayles and John Waters.

Maggie Gyllenhaal plays a young woman recently released from a mental institution who becomes the secretary of a demanding attorney (James Spader), who starts a sadomasochistic relationship with her that spins out of control.

Gillian Robespierre directed and co-wrote this film that subverts the rom-com genre in telling the story of a comedienne (Jenny Slate) whose fling with a graduate student results in an unplanned pregnancy, causing her to address the challenges of independent womanhood.

Billy Wilder produced, directed, and co-wrote this farce about the son (Jack Lemmon) of a millionaire who goes to the Italian island of Ischia to recover the body of his deceased dad and uncovers less-savory aspects of his dead father’s life. While in Italy he has a romantic relationship with a free-spirited Brit (Juliet Mills). This was one of seven Wilder and Lemmon collaborations.

Directed and written by Paul Thomas Anderson, “Licorice Pizza” takes place in California’s San Fernando Valley in 1973, and is about the first love of a teen (Cooper Hoffman – Philip Seymour Hoffman’s son) who sets his sights on a young woman living a purposeless life.

Another rom-com/drama written and directed by Paul Thomas Anderson, this film stars Adam Sandler as a sexually frustrated man whose call to a phone-sex line triggers an unfortunate set of events that could complicate his budding relationship with a mysterious woman (Emily Watson). The film is darker than other rom-coms Sandler has appeared in.

A galaxy of stars distinguishes this quintessential date movie about a high school reunion at which Willie (Tim Hutton), Tommy (Matt Dillon), and Paul (Michael Rapaport) are prepared to connect with “beautiful girls” Lauren Holly, Natalie Portman, Mira Sorvino, and Uma Thurman. The film featured three Oscar winners: Hutton, Portman, and Sorvino.

The sometimes ribald rom-com stars Jason Segel as Peter Bretter, a man whose newswoman girlfriend ( Kristen Bell) dumps him for a rock star (Russell Brand). Depressed by the rejection, Peter goes on holiday to Hawaii, where his ex and her new boyfriend are also vacationing. Paul Rudd, Mila Kunis, and Bill Hader buoyed the film.

This rom-com with a time-travel twist stars Domhnall Gleeson as a 21-year-old Englishman who is told by his dad (Bill Nighy) that the men in their family can travel in time. After his doubts are overcome, he tries to change his life through time travel and find a girlfriend. But he can’t change history, and the circumstances that affect his family can’t be altered either. The film was directed by Richard Curtis, the rom-com vet who made “Love Actually” and “Four Weddings and a Funeral.”

The breakthrough film for Spike Lee, who wrote, produced, directed, and starred in this comedy. “She’s Gotta Have It” is about a young African-American woman named Nola (Tracy Camilla Jones), who can’t decide which of three young men should be her boyfriend – so she dates all of them.

Rom-coms aren’t usually very political, but “Strawberry and Chocolate,” co-directed and co-written by Tomás Gutiérrez Alea, is an exception. In Castro’s Cuba in 1979, gay artist Diego tries to seduce straight government guy David and fails. David maintains their association so he can monitor Diego’s lifestyle. As they discuss politics, a true friendship develops. “Strawberry and Chocolate” was the first Cuban movie nominated for Best Foreign Film at the Oscars.

This is a rom-com vehicle for Steve Carell, who plays a 40-year-old employee of a consumer electronics store who has yet to do the deed. But opportunity comes in the person of a single mom (Catherine Keener), who is searching for a nice guy. The sometimes raunchy comedy, famous for its chest-hair-waxing scene was boosted by cast members Paul Rudd, Seth Rogen, Romany Malco, and Elizabeth Banks.

Fun-boy Ben (Seth Rogen) and ambitious newswoman Alison (Katherine Heigl) have a one-night stand that results in a pregnancy. The two decide to raise the child and weigh the possibility that they might be right for each other. The strong supporting comedic cast includes Paul Rudd, Leslie Mann, Jason Segel, Kristen Wiig, and Bill Hader.

Critics raved about the chemistry between Hugh Grant and Andie MacDowell as an Englishman and an American who meet at a wedding and have a one-night affair. When she returns to the U.S., that seems to end the relationship. But they keep running into each other at other nuptials and even a funeral, suggesting that they were meant to be together.

Billy Eichner co-wrote and starred in this pioneering rom-com about two gay men with very busy lives haltingly moving toward a relationship.

Kevin Smith, whose movies follow the lives of suburban slackers, wrote and directed “Chasing Amy,” a rom-com with a twist. Comic book artists Holden (Ben Affleck) and Banky (Jason Lee) are happy with their lives. Then they meet Alyssa, also a comic book artist. Holden falls in love with her, but is shocked to find out that she’s a lesbian.

In “Up in the Air,” George Clooney plays a soulless, rootless corporate gun for hire who is retained to fire people, spending his life jetting from city to city to ply his trade. His life becomes more complicated when he meets a potential love interest (Vera Farmiga), and a new assistant (Anna Kendrick) who has him rethinking his life.

Noah Baumbach and Greta Gerwig co-wrote this rom-com about Frances Ha (Great Gerwig), an aspiring dancer who goes from apartment to apartment in Brooklyn in pursuit of a stable relationship. Critics hailed Gerwig’s star turn .

Cultural taboos take a beating in “Saving Face,” a Chinese-themed rom-com. Wil (Michelle Krusiec) is a lesbian in a relationship with Vivian (Lynn Chen) – but she can’t tell her traditional widowed mother. Her mom (Joan Chen) has her own secret – she’s pregnant and unmarried. Mom’s parents kick her out of their house and she’s forced to live with her daughter. All ends well, with Wil and Vivian going public and Wil’s mother goes off with the unlikely father of her child.

Zach Braff wrote, directed, co-starred in this rom-com about a young actor who returns to his small town in New Jersey for his mom’s funeral. While dealing with the family he is estranged from, he’s attracted to an amateur musician (Natalie Portman).

Directed by TV veteran James L. Brooks (“The Mary Tyler Moore Show,” “Taxi”), “Broadcast News” is about an ambitious television news producer who falls for a handsome news anchor, while her best friend, a TV news professional, develops a professional and romantic rivalry with the newcomer.

Benefitting from a cast of top actors, “Bull Durham” is one of the funniest takes ever on life among minor league baseball players. Sarandon is the groupie love interest of the players. The movie holds a 97% Rotten Tomatoes score.

“Silver Linings Playbook” is a rom-com about two broken people who find each other – not exactly an original plot, but one that’s handled well here. Jennifer Lawrence won a best actress Oscar for her role as a recently widowed woman who becomes involved with a recently separated and troubled man portrayed by Bradley Cooper.

Mira Nair (“Mississippi Masala,” “Salaam Bombay!”) directed this movie about the pressures posed by a traditional Indian wedding on everyone involved, including a stressed-out father, a bride-to-be in love with someone else, an event planner, and assorted relatives.

Rob Reiner-directed and Nora Ephron wrote this rom-com starring Billy Crystal and Meg Ryan as two people trying, and ultimately failing, to maintain a platonic relationship. The film is famous for Ryan’s “I’ll have what she’s having” scene at Katz’s Deli in Manhattan.

Éric Rohmer wrote and directed this French film (also known as “Chloé in the Afternoon” in English and “L’amour l’après-midi” in French) about a love triangle involving a lawyer (Bernard Verley), the wife he’s devoted to (Françoise Verley – Bernard’s real-life wife), and a woman from the lawyer’s past (Zouzou), with whom he is having an intimate but non-sexual affair.

This Chinese romantic comedy, directed by Ang Lee, is about a gay Chinese man living in New York and the pressure he’s under from his traditional parents to get married. The solution is a marriage of convenience with a Taiwanese girl who can stay in the U.S. if she weds the man.

This unhinged rom-com from the mind of director Emir Kusturica is about a low-level Roma criminal who tries to pay a debt by marrying off his adolescent son in an arranged marriage with his partner’s sister – but neither son nor sister are happy about the nuptials. The film enjoys a 95% Rotten Tomatoes audience score, equaling the highest of any movie on our list.

One of the newer entries on our list is this Norwegian dramedy, which follows the life and loves of an aimless young woman (Renate Reinsve) in Oslo over the course of four years. Joachim Trier directed and co-wrote the movie – part of his Oslo trilogy. It was nominated for two Oscars.

Emily V. Gordon and her husband, comedian Kumail Nanjiani, drew upon their own experiences when co-writing this romantic comedy about culture clash. Nanjiani played a Pakistani stand-up comic who develops a bond with the wary parents (Ray Romano and Holly Hunter) of his comatose American girlfriend.

“Manhattan” is a Woody Allen valentine dedicated to his favorite city, featuring people as socially dysfunctional and neurotic as the characters he always plays. In this film, Allen portrays a divorced television writer who is falling in love with his best friend’s mistress (Diane Keaton – Allen’s real-life ex-girlfriend). The music of George Gershwin is featured.

Mixing comedy with whimsy, “Amélie” tops our list of the best R-rated rom-coms. The French movie’s title character (Audrey Tautou), an unassuming waitress with an innocent’s worldview, benignly orchestrates the lives of those around her and metes out her own brand of justice. In the course of her efforts to help others, she finds love.