The 20 best romantic comedies to stream on Valentine’s Day

If any genre has an all-too-recognizable formula, it’s the romantic comedy (aka rom-com). There’s usually a lie involved, or something supernatural that happens, and then everything works out just fine, oftentimes with a wedding or a baby on the way. Sometimes those tropes are used in fresh ways, and sometimes they’re not used at all, as demonstrated in our roundup of 20 stream-worthy romantic comedies, hailing from the 1930s all the way up to last year.

We’ve incorporated a wide range of romances here, as it’s all too clear that most movies made over the past century or so have been focused on white, heteronormative relationships. Happily, that has begun to be corrected. There’s room for everybody. All these movies have two things in common: love and laughs. Happy Valentine’s Day!

Trouble in Paradise

Stream it on Criterion Channel

This pre-code masterpiece was directed by Ernst Lubitsch, a filmmaker largely unknown today but famous during his time for his “Lubitsch Touch.” This was a way of describing his instantly recognizable, but impossible-to-describe style, a unique rhythm, and a deft deflection. In Trouble in Paradise (1932), the main character, a master thief named Gaston Monescu (Herbert Marshall) spends many moments running up and down a flight of stairs. These moments might not have anything to do with the story, but they change the timing of the scene, stretching things and making the laughs bigger and cleverer.

The romantic story has Gaston meeting and falling for another thief, Lily (Miriam Hopkins). They decide to team up and rob a purse from perfume magnate Madame Colet (Kay Francis), then return it and collect the reward money. But Gaston sees an opportunity for an even bigger haul and talks his way into a job as her assistant. Unfortunately, she falls for him, and he may be falling for her, too. And there are two other suitors (Charlie Ruggles and Edward Everett Horton), the latter of which was one of Gaston’s former victims. Many consider this to be the most polished and crystalline of Lubitsch’s films, with Hopkins giving one of history’s great comedy performances.

Bringing Up Baby

Stream it on HBO Max

Bringing Up Baby (1938) is an early example of the free-soul-meets-uptight-schlub movie, but as directed by the masterful Howard Hawks, it might be the most perfectly constructed—and fastest-moving—of all screwball comedies. Cary Grant—done up to look like silent comic Harold Lloyd—plays paleontologist Dr. David Huxley, who only needs one more bone (the “intercostal clavicle”) to complete his Brontosaurus skeleton. He’s also about to be married to the dull and loveless Alice (Virginia Walker). He heads out to a country club to coax money from a wealthy socialite, and he runs into the kooky and beautiful Susan (Katharine Hepburn), who ruins everything.

Before long, Susan’s dog (Asta, from the Thin Man movies) has stolen the clavicle and buried it. Meanwhile, Susan has adopted a tame leopard called “Baby,” which, of course, gets confused with a wild one. Hawks spins this story at lightning speed, keeping us off-balance enough that all the jokes land with big laughs; but somehow, it’s constantly fresh and never tiresome.

The Lady Eve

Stream it on Criterion Channel

Preston Sturges talked his way into becoming one of the rare writer/directors of his time, making an incredible batch of eight great comedies in just five years. Of these, The Lady Eve (1941) had the biggest stars and the most romantic story, but it’s also one of the flat-out funniest. Charles Poncefort Pike (Henry Fonda) is the wealthy heir to an ale company, but is more focused on studying snakes, and is too shy to bother with women. Returning after a year in the Amazon, Charles is targeted by con artist Jean Harrington (Barbara Stanwyck), who subsequently falls in love with him.

Thanks to meddling by Jean’s card shark father (Charles Coburn) and Charles’ protector Muggsy (William Demarest), Charles breaks up with her. She returns in disguise, as “The Lady Eve,” to get her revenge. Peppered with an amazing crew of character actors, including the frog-voiced Eugene Pallette, all reading Sturges’s sharp, snappy dialogue, this is one of those movies that ensures you’ll miss the next joke if you laugh too long at the last one. Perhaps best of all is the clever way Sturges was able to slip in all kinds of sly innuendo and sophisticated humor so smart it slipped right by the censors in the Hays office.

Roman Holiday

Stream it on Paramount+, PlutoTV, or Kanopy

Audrey Hepburn had been in a few bit parts before she landed this starring role, one of the most luminous and romantic characters in cinema history. She was a huge hit and won an Academy Award for her performance. Roman Holiday (1953) was directed by the prestigious William Wyler, but even he seemed to sense the lightness and romance of the material, and it’s one of his breeziest efforts. Gregory Peck plays a down-on-his-luck American reporter in Rome. He finds a young woman (Hepburn) sleeping on a bench and, not knowing what to do with her, takes her to his apartment.

When he realizes that she’s Princess Ann, who has run away from her boring royal duties to see a little of the world, he bets his editor that he can get an exclusive interview with her. He convinces her to let him show her around, and they are eventually joined by Joe’s photographer pal Irving Radovich (Eddie Albert). After a while, Joe begins to feel bad about his scheme, and, of course, falls in love. With a screenplay by the blacklisted Dalton Trumbo (his name was digitally added to the credits in the early 2000s), and Wyler’s travelogue-style black-and-white filmmaking, the movie has a freshness that never feels dated.

The Princess Bride

Stream it on Disney+

Everyone knows it and loves it, but at the time, it wasn’t a huge success; some opined that the sluggish box office was due to the “girly”-sounding title. Directed by Rob Reiner during a hot streak, The Princess Bride (1987) is one of those movies that just feels perfect; every beat, every joke, every cut, and every shot seems absolutely right. In a wraparound sequence, a kindly grandpa (Peter Falk) visits his sick grandson (Fred Savage) and offers to read him a story. (“Is this a kissing book?” he asks.) Then we get the rousing adventure of a Farm Boy (Cary Elwes) who becomes a dashing pirate, his love for the beautiful Buttercup (Robin Wright), and his efforts to rescue her from the sneering Prince Humperdinck (Chris Sarandon).

The brilliant cast includes Mandy Patinkin as vengeance-seeking swordsman Inigo Montoya, Christopher Guest as the six-fingered Count Rugen, Wallace Shawn as Vizzini (“Inconceivable!”), André the Giant as Fezzik, Billy Crystal as Miracle Max, and Carol Kane as Max’s wife Valerie. William Goldman adapted the screenplay from his own 1973 novel, and Mark Knopfler of Dire Straits provided the gentle, string-based music. Reiner went on to direct another romantic comedy, the seminal When Harry Met Sally….

Moonstruck

Stream it on Showtime

Even though it was directed by Oscar favorite Norman Jewison—who usually specialized in serious, nominatable movies—the brisk romantic comedy Moonstruck (1987) still holds up remarkably well today, thanks to its snappy patter, warmth, and lovable misfit characters. Cher, who won a Best Actress Oscar, plays Loretta Castorini, a widow living with her loud, Italian family in Brooklyn. She believes she is cursed (her husbands keep dying), but she reluctantly accepts a marriage proposal from a new man, Johnny Cammareri (Danny Aiello). He asks her to find his estranged brother and invite him to the wedding.

That turns out to be the passionate, sad-eyed Ronny (Nicolas Cage), who wears a prosthetic hand and who instantly strikes sparks with Loretta. It contains all the usual rom-com moments, including a “makeover” scene, but it’s unusually smart and lively. It feels genuine. Olympia Dukakis won an Oscar and Vincent Gardenia was nominated for their performances as Loretta’s very funny, grousing parents. Playwright John Patrick Shanley won an Oscar for his screenplay.

Coming to America

Stream it on HBO Max

In hindsight, it would have been nice to hire a Black person to direct this hit comedy, but as it stands, John Landis does a bang-up job, applying his singular style and rhythm—sitting somewhere between Ernst Lubitsch and Chuck Jones—to the story. Coming to America (1988) begins in the African nation of Zamunda, where, on his 21st birthday, Prince Akeem (Eddie Murphy) has grown tired of the constant pampering he receives. He also objects to the arranged marriage his father, the king (James Earl Jones), has forced upon him. So, he arranges a trip to New York, accompanied by his loyal sidekick Semmi (Arsenio Hall), in hopes of finding his own partner.

Akeem can’t let on that he’s royalty, of course, so he gets a job in a local hamburger joint, where he meets the manager’s pretty daughter, Lisa (Shari Headley). It’s really all about love and honesty triumphing over superficiality (something the 1980s specialized in), and it’s very funny besides. The barbershop sequences, featuring Murphy in heavy makeup as an old Jewish man and a Black barber, plus Hall and Clint Smith (Murphy’s childhood pal) as two other barbers, are still classic. Many notable character actors appear in either cameos or early roles (Cuba Gooding, Jr., for example, plays “boy getting haircut”).

Four Weddings and a Funeral

Stream it on HBO Max

A massive hit and an Oscar-nominee for Best Picture and Screenplay, Four Weddings and a Funeral (1994) distinguishes itself with its opening scene, as our hero Charles (Hugh Grant) and his sister Scarlett (Charlotte Coleman) wake up and realize that they are late for a wedding. Rather than the expected polite English comedy, the siblings start dropping F-bombs as they hastily dress and then break traffic laws to make it on time.

Set during the course of, yes, four weddings and a funeral, the movie follows the exploits of Charles and his hopeful romance with American Carrie (Andie MacDowell), as well as various romances of the colorful supporting cast. The movie was surprisingly diverse for its time, as well, with a gay couple and a deaf character among the friends. Kristin Scott Thomas co-stars as sharp-tongued Fiona, and with John Hannah, Simon Callow, and Rowan Atkinson as “Father Gerald,” who hilariously mangles his wedding sermon. Richard Curtis wrote the milestone screenplay and became the go-to man for many more romantic comedies to come.

Clueless

Stream it on Paramount+ or PlutoTV

In the 1990s, Hollywood was Jane Austen crazy. Several polite, English-style adaptations were released one-by-one, but the most entertaining one was arguably Amy Heckerling’s Clueless (1995), which took the plot outline from Austen’s Emma and transferred it perfectly to a Beverly Hills high school, with class struggles intact. The heroine is now Cher (a great Alicia Silverstone), who, along with her friend Dionne (Stacey Dash), was “named after great singers of the past.” She decides to give a makeover to a tragically unhip new girl, Tai (Brittany Murphy), but then her troubles start when her matchmaking attempts go in the wrong direction. More awkwardly, she finds herself falling in love with her ex-stepbrother Josh (Paul Rudd).

Director Heckerling (Fast Times at Ridgemont High) keeps the movie bright and sunny, with decorative primary colors, and invests totally in Cher’s confidence in her own misguided decisions; it’s a highly appealing, constantly hilarious combination. Breckin Meyer is very funny as a skakeboarder who shows interest in Tai, Donald Faison plays Dionne’s braces-wearing boyfriend, Wallace Shawn is a teacher, and Dan Hedaya is brilliantly deadpan and grumpy as Cher’s dad.

Notting Hill

Stream it on Netflix

An argument could be made that Julia Roberts has never been better than she is in Notting Hill (1999), where she plays a luminous movie star; it’s the only place her onscreen character matches her considerable presence. Maybe the story of a romance between Anna Scott (Roberts) and Will, a humble English bookshop owner is far-fetched, but screenwriter Richard Curtis (Four Weddings and a Funeral) and star Hugh Grant manage to make it work, relying on realistic romantic barriers having to do with fame. And Roberts and Grant do have a delightful onscreen chemistry.

As with Curtis’s other screenplays, there’s a huge cast of colorful best pals, including the hilarious Rhys Ifans as Will’s truly horrible housemate Spike. A great sequence occurs at a surprisingly authentic press junket, where Will finds himself masquerading as a reporter from Horse and Hound magazine and pretending to interview Anna. But just as memorable is the “I’m also just a girl, standing in front of a boy” line, which still melts hearts.

50 First Dates

Stream it on Peacock Premium

Adam Sandler and Drew Barrymore have so far made three movies together; many prefer The Wedding Singer (1998), but 50 First Dates (2004) is surprisingly disarming, and not easy to forget. It’s far from a perfect movie, thanks to dumb gross-out gags and Rob Schneider in dark makeup (playing a Hawaiian native), but when it gets to the heart of the matter, the rest falls away.

Sandler plays Henry, a veterinarian at a Hawaiian aquatic park, who avoids romantic attachments and sticks to seducing tourists. One day he meets Lucy (Barrymore), and they make an instant connection, but the next day, she cannot remember him. It turns out she has amnesia, due to a car accident, and every time she sleeps at night, she forgets the day. But Henry keeps trying, fighting through many painful/funny setbacks to win her heart.

Memorably, Sean Astin and Blake Clark play Lucy’s brother and father, who dutifully pretend that it’s her birthday every night, gifting her with a video of The Sixth Sense, watching it every night, and pretending to be surprised by its twist. It’s a sweet, touching movie, in which Barrymore radiates adorableness, and Sandler gives one of his gentler performances.

Bridesmaids

Stream it on Amazon Prime Video

Even though it centers around a wedding, Bridesmaids (2011) is far from a typical rom-com. It’s mostly centered on that rare thing in movies: female friendships. Kristen Wiig—who co-wrote the screenplay with Annie Mumolo—stars as Annie Walker, whose life is in the pits after the recession killed her bakery business and wiped out her savings. Her best friend Lillian (Maya Rudolph) is getting married, and has become close with one of her bridesmaids, Helen (Rose Byrne), a friend of her fiancé. Annie and Helen find themselves in fierce competition for Lillian’s friendship, with Annie frequently losing, either thanks to bad luck, or to Helen’s sinister cunning.

One sequence has the entire wedding party exploding with diarrhea while shopping for dresses after eating Brazilian food at a restaurant Annie suggested. Annie does meet a nice man, a police officer (Chris O’Dowd), who pulls her over, but that’s hardly the point of the story. Melissa McCarthy received her first Oscar nomination for her hilarious supporting performance as Megan, a woman with a foul mouth and a supernatural level of confidence. Wiig and Mumolo’s screenplay also received a nomination.

Always Be My Maybe

Stream it on Netflix

Co-written by and starring Randall Park and Ali Wong, the delightful Always Be My Maybe (2019) follows a pretty standard romantic comedy formula, but it’s so constantly, surprisingly fresh and bracing along the way that it feels like something new; it’s crazier and richer than even Crazy Rich Asians. Park and Wong play childhood friends who have a falling out after an awkward attempt at teenage sex. As adults, Wong has become an ambitious celebrity chef and Park is content performing his silly, catchy hip hop songs in whatever small, local San Francisco venues will have him. Wong arrives in town to open a new restaurant, and all the old feelings tumble out again.

With Park’s unhurried delivery and Wong’s frantic intensity, the two stars have a perfectly complementary chemistry, and Keanu Reeves’s hilarious much-memed cameo is the icing on top. Daniel Dae Kim and Vivian Bang play the romantic rivals, and Fresh Off the Boat creator Nahnatchka Khan directs.

Palm Springs

Stream it on Hulu

Hulu’s second “time loop” movie after Boss Level, the romantic comedy Palm Springs (2020), is so loose, cheerful, funny, clever, adorable, and thoroughly entertaining, that many film critics named it one of the best films of the year. (According to Metacritic’s roundup of lists, it was ranked the 12th best film of 2020.) It’s one of those films that was sorely needed during the pandemic year, a tonic for jangled nerves.

Andy Samberg plays Nyles, stuck in a time loop on the day of a friend’s wedding. The movie cleverly lets us get through one day before letting us know that Nyles has been in this loop for some time, and has learned to just enjoy himself the best he can. On this particular day, however, he accidentally brings Sarah (Cristin Milioti) along with him, and she becomes stuck too. As the couple deals with their feelings for each other, and Nyles’s past within the loop, they must decide whether to relax and enjoy, or try to break out. J.K. Simmons co-stars in a great performance as yet another time-looper with a different agenda.

The Lovebirds

Stream it on Netflix

The Netflix original The Lovebirds (2020) is something of an action/romantic/comedy, but brisk and silly as well as consistently hilarious and actually romantic. We meet Jibran (Kumail Nanjiani) and Leilani (Issa Rae), who have a spectacular first date, and then we cut to four years later, as they live together and fight regularly. One night, while on their way to a dinner party, they accidentally hit a bicyclist with their car. A man claiming to be a police officer commandeers the car, chases the frightened cyclist, and uses the couple’s car to finish the job, running over and killing the poor victim, and leaving Jibran and Leilani looking like murderers.

Unable to go to the police due to the color of their skin, they grab the cyclist’s phone and head out into the night to clear their names. Director Michael Showalter (Nanjiani’s The Big Sick) keeps things nicely balanced between characters, jokes, and silly situations, and brings it all in in just 86 minutes, while Nanjiani and Rae share a wonderful onscreen chemistry, as well as an irresistibly snappy banter.

The Half of It

Stream it on Netflix

Edmond Rostand’s 1897 play Cyrano de Bergerac has been adapted into many movies—including versions starring José Ferrer, Gérard Depardieu, Steve Martin, and Peter Dinklage—but none are quite like The Half of It (2020). This time the Cyrano character—an outcast who has an unrequited romantic longing and a way with words—is Ellie Chu (Leah Lewis), a shy, sad high-school student in the town of Squahamish. She covers her grieving father’s job as a railroad station master and makes money writing papers for other students. She’s approached by football player and secret sausage chef Paul Munsky (Daniel Diemer) and hired to write a letter to the pretty Aster Flores (Alexxis Lemire). Of course, Ellie falls for Aster as well, and their written exchanges are as passionate as Aster’s verbal exchanges with Paul are awkward.

Remarkably, the movie avoids most of the cliches involving the “lie plot,” as the characters and their interactions grow subtler and more complex. It even manages a fairly realistic and satisfying ending without feeling tacked-on or phony. This one is a real treasure.

On the Rocks

Stream it on Apple TV+

Sofia Coppola’s screwball comedy might seem like a lightweight throwaway, but graced with her masterful, gentle touch, On the Rocks (2021) turns into something special. It tells the simple story of a New York woman, Laura (Rashida Jones), who begins to suspect that her marriage to Dean (Marlon Wayans) is in trouble. While dining out to celebrate Laura’s birthday, a server brings out a dessert topped with lit candles, to, and then past, their table. Their faces tell the whole story; Laura is crestfallen and Dean realizes that he should have thought of that.

In any case, Bill Murray plays Laura’s well-meaning but largely irresponsible father Felix—it’s a most Murray-like role—who tries to help his daughter save her marriage, through some very unorthodox methods. There are so many moments that deftly evade cliché, while bringing the laughs, and often becoming unexpectedly beautiful, such as a sequence in which Felix and Laura try to sneak out of a party (“walk backwards, so it doesn’t look like we’re leaving”) and stop to admire a Monet hanging in an empty hallway. It’s a simple, delightful movie, perfectly constructed, yet with time to breathe.

Anything’s Possible

Stream it on Amazon Prime Video

A Broadway star and Emmy winner for the TV series Pose, Billy Porter makes his directing debut with Anything’s Possible (2022), an inclusive, progressive, high-school comedy-romance that goes a long way toward rectifying the social and cultural errors of movies of similar movies from the 1980s and 90s. Kelsa (Eva Reign) is a proud Black trans girl, and Muslim Khal (Abubakr Ali) has a crush on her. She likes him back and they begin dating, but their relationship causes chaos with Kelsa’s friend Em (Courtnee Carter), who also liked Khal, and with Khal’s best friend Otis (Grant Reynolds), who is trans-phobic.

The dialogue is open and exploratory, with characters expressing strong opinions, listening to one another, and adjusting ideas. It’s remarkably direct and mature for a high-school movie, even if it shies away from exploring the physical side of the relationship (aside from lots of smooching). Kelly Lamor Wilson plays Kelsa’s other best friend, the “honey badger” Chris.

Bros

Stream it on Peacock Premium

Coming from the team of writer/actor Billy Eichner, writer/director Nicholas Stoller (Forgetting Sarah Marshall), and producer Judd Apatow, Bros (2022) is—about time—the very first gay-themed romantic comedy ever released by a major studio. It traces the old bones of rom-com formulas, but remains wise about them, twisting and subverting them at every step. The result is hilarious and unexpectedly poignant, both familiar and groundbreaking. Bobby (Eichner) is struggling to open the first LGBTQ+ museum in Los Angeles. At a club, he meets handsome Aaron (Luke Macfarlane), an unhappy lawyer who dreams of opening a chocolate shop.

Bobby and Aaron both prefer casual hookups to relationships, but as they spend time together, they discover—to their horror—that they are very good for each other. But before long, they face real relationship challenges (family, jealousy, etc.). There’s an affectionate parody of Hallmark Christmas movies (of which Macfarlane is a frequent star), and Bowen Yang is hilarious as a bonkers millionaire whom Bobby hopes to hit up for a donation.

The Lost City

Stream it on Amazon Prime Video

One of the great rom-com queens, Sandra Bullock, stars in this Romancing the Stone-like adventure. It’s familiar, yes, but with enough fun, sweet stuff inside to earn it a closing spot on our Valentine’s Day list. Bullock plays Loretta Sage, a successful romance novelist who is widowed and generally unhappy with her life. Her publisher (Da’Vine Joy Randolph) forces her to go on tour with her cover model, Alan (Channing Tatum), whom fans regularly confuse with Loretta’s fictional character “Dash McMahon.” Loretta is kidnapped by billionaire Abigail Fairfax (Daniel Radcliffe) and forced to help him find a priceless treasure, based on clues written in her books. Before long, Alan and Loretta find themselves escaping through the jungle, even though neither of them are exactly experts at survival.

The Lost City (2022) gets most of its energy from the snappy byplay of its two stars; the jokes slowly turn into confessions that feel organic, although Randolph, Radcliffe, and Brad Pitt—who plays an uber-cool man-of-action—get plenty of laughs as well. Plus, it’s refreshing to see Bullock, now in her late 50s, still at her best.