The romantic comedy genre has been under much duress over the last few years since the streaming giants have taken over. Though 2023 introduced audiences to successful, theatrically released rom-coms like the Jennifer Lawrence-led No Hard Feelings and the recent hit Anyone But You, the genre still exists mainly in places like Netflix, Prime Video, and Peacock. Especially with studios leaning heavily on pre-existing properties and IP, the romantic comedy has been boxed out since having the big-budgeted success it once had.
The heyday period ended recently, and through the 1990s, early 2000s, and even a few years ago, romantic comedy was a reliable source of box office revenue. Stars like Cameron Diaz, Julia Roberts, Meg Ryan, Tom Hanks, and even Jennifer Lopez rode the tails of their superstore on the genre fair of romance. Films like My Best Friend's Wedding made $300 million, but today that seems unthinkable and impossible.
Since the influx of romantic comedies has died down and some films have left their cultural imprint over the last 25 years — 500 Days of Summer, Love Actually, Easy A, and High Fidelity — these are some that may have slipped through the cracks. But still deserve their due praise and possibly reach a new audience.
Updated December 26, 2023: To keep this article fresh and up-to-date, additional content and romantic comedies have been added to this article.
15 Enough Said (2013)
Enough Said
- Release Date
- September 18, 2013
- Rating
- PG-13
Before the light eventually burned out tragically on one of America's most significant screen presences, James Gandolfini shone in Nicole Holofcener’s Enough Said. With a warmth that captures each frame, Gandolfini fits perfectly into the indie filmmaker's brand of small, quirky, and humanist dramedy. Opposite Julia Louis-Dreyfus, the two find a peculiar chemistry as Dreyfus’ character balances the fallout out of discovering Gandolfini’s character is the ex of the self-help guru (Catherine Keener), who is guiding her life in a positive direction.
What Makes It Memorable
Enough Saidhas all the charm of a successful romantic comedy with enough character specifics thanks to its talented group of actors to create a winning premise. Gandolfini and Louis-Dreyfus brilliantly play off one another with their effortless on-screen camaraderie, and the dynamic duo garnered widespread acclaim when the engrossing picture debuted at the Toronto International Film Festival, with the actress also earning a Golden Globe nod for her performance. Enough Said was posthumously released after Gandolfini's devastating passing, and it winningly captures the star's unparalleled magnetism. Rent or buy on Prime Video.
14 The Heartbreak Kid (2007)
The Farrelly Brothers often find the sweet spot between the gross, over-the-top comedic set pieces that made them famous with tender and heartfelt romance. Teaming once again with There’s Something About Mary alum Ben Stiller, The Heartbreak Kid saw the writer-director duo in a similar terrain. A remake of the '70s flick, the rom-com also features the funny man sharing the screen with dad Jerry Stiller, who hilariously appears as his character's foul-mouthed father.
What Makes It Memorable
While not possessing the same cultural impact, Stiller found a way to take his zany and manic energy, channeling it into a marriage gone awry when he realizes he's made a mistake. With Malin Ackerman still on her run of leading movies, she turns out to be a nutcase that Stiller can't handle, and he finds love on their honeymoon with someone different. The film is full of memorable moments but none take the cake like the car ride from hell as Ackerman sings her way obnoxiously through song after song, tormenting Stiller to no end. Stream on Paramount+.
13 Sleeping With Other People (2015)
Leysle Headland has gone on to huge success with her highly popular Netflix show Russian Doll. But, before her television takeover, she was on the indented scene making hilariously heartfelt and raunchy romantic comedies. Sleeping with Other People tells the amusing story of a perpetual cheater and lovable womanizer who, after having a passionate one-night stand 12 years earlier, reconnects and attempts to keep things platonic as friends, though naturally, love has other ideas for the pair.
What Makes It Memorable
Headland set out to create a film about sex addiction after a personal bout with depression, and during the writing process, the project inadvertently emerged as a rom-com, so the director wanted to make sure "that it all felt very believable" (via Cosmopolitan). The refreshing flick was backed by the stellar pairing of Allison Brie and Jason Sudeikis, whose sensational chemistry jumps off the screen. Also rounded out by a never creepier Adam Scott as he whirls Brie into a love affair, Sleeping With Other People deftly taps into the anxiety of sex and what it does to friends or people in existing relationships. Stream on Hulu.
12 Blast from the Past (1999)
In the throes of being a superstar, 1999 was a year to celebrate Brendan Fraser. Between The Mummy and its box-office success, Blast from the Past was a flop, but one that gave Fraser the space to show his commitment to performance and his manic energy that slides perfectly into a comedic pocket, playing a man who spent the first 35 years of his life in a fallout shelter because his wonky, scientist dad (Christopher Walken) was terrified of a nuclear holocaust.
What Makes It Memorable
The chemistry between Fraser and Alicia Silverstone, who guides the naivety of the goofy Fraser, makes for a silly and endearing romance. Especially in 1999, a year jam-packed with great films. Blast from the Past is jam-packed full of zany humor and delightful hijinks, and Fraser is able to showcase his irresistible charisma and likability as the sheltered leading man. Rolling Stone commended the Oscar-winning actor's uninhibited performance, writing in their glowing review, "Blast From the Past doesn't overtax Fraser's abilities — the film is only a sweet comic confection — but director and co-writer Hugh Wilson does rely on a rare quality that Fraser has in spades: charm." Rent or buy on Prime Video.
11 Definitely, Maybe (2008)
Definitely, Maybe
- Release Date
- February 8, 2008
- Director
- Adam Brooks
- Cast
- Ryan Reynolds , An Nguyen , Matthew Mason , Rick Derby , Sakina Jaffrey , Bob Wiltfong
- Rating
- PG-13
A heart-stirring turn from Ryan Reynolds, still fresh into his career before leaning fully into the swarm and sarcasm that elevated him to Marvel hero superstardom, Definitely, Maybe is a triptych of romance as Reynolds explains to his daughter (a lovely Abigail Breslin) how she came to be through three — Rachel Weisz, Elizabeth Banks, and Isla Fisher — of his most important relationships.
What Makes It Memorable
Reynolds keeps the women's names in anonymity as the film relies heavily on flashbacks, reliving the history of the early-90s and what it means to find love — even when it ends. The tender and heartfelt scenes shared between Reynolds and Breslin truly propelled the wholesome story, and audiences were left wondering right along with the young Breslin just who her mother was in her father's captivating recollections. Stream on Max.
10 What If? (2013)
what if
- Release Date
- September 7, 2013
- Rating
- PG-13
Hot off the heels of his decade-long run as the legendary wizard Harry Potter, Daniel Radcliffe opted to embrace the romantic comedy genre when he appeared alongside Zoe Kazan in What If? The playful picture centers on the disenchanted young man Wallace as he finds himself desperately trying to fight his growing attraction to the bubbly Chantry, who has been in a committed relationship for years. Despite her relationship status, Wallace and Chantry swiftly realize they share a bond that simply can't be ignored.
What Makes It Memorable
With an impressive supporting cast including Adam Driver, Mackenzie Davis, and Megan Park, What If? granted Radcliffe the chance to star in a contemporary film, as he had never done so previously and felt it was something he wanted to give a whirl. Radcliffe and Kazan improvised many of their lines and dialogue in the engaging flick, doing so in order to create a natural and easy atmosphere that superbly translated to the finished product. Stream on Paramount+.
9 Two Can Play That Game
Finding a stellar role for Vivica A. Fox, who thrives as she narrates and tears down the fourth wall, directing her voice straight to the audience, Two Can Play That Game is a fun, bold take on the romantic comedy. Finding a way to keep her man in line as she navigates corporate and domestic issues, Morris Chestnut plays the opposite as he starts to get the allure of other women.
What Makes It Great
With a knockout supporting cast including an improv-laden diatribe extraordinary performance from Anthony Anderson, as he tries wedging his insane personal beliefs onto Morris Chestnut, the film is quick 90 minutes of laughs and heartache. A true gem of the early-2000s, Two Can Play That Game spawned a less-than-memorable 2007 sequel (with Fox reprising her role) and the actress even starred in a stage production of the rom-com in 2017, once again demonstrating her talents as the feisty and capable lead character. Rent or buy on Prime Video.
8 Timer (2009)
timer
- Release Date
- May 14, 2009
- Rating
- R
Buffy the Vampire Slayer star Emma Caufield headlined the independent sci-fi rom-com Timer, which takes place in a world in which people are implanted with a device in their wrist that counts down to the day when they will find their one true love. Los Angeles orthodontist Oona makes the disheartening discovery that her soulmate is not equipped with a timer, so she sets out on a mission to figure out who her Mr. Right is while coping with the uncertainty and wonder of when they will meet.
What Makes It Memorable
Timer masterfully blends sci-fi with romance and touts an intriguing premise that instantly hooks audiences, with Caufield serving up an earnest and pleasant portrayal of the love-seeking Oona. Timer was directed and written by Jac Schaeffer in her directorial debut, and the filmmaker would go on to create the Marvel miniseries WandaVision and co-write the story for Black Widow. Timer remains an underappreciated 2000s rom-com that showcases the talents of both Caufield and Shaeffer. Currently unavailable for streaming.
7 Win a Date with Tad Hamilton! (2004)
Honing in on the classic romantic comedy setup where friends turn to lovers after a final revelation, Win a Date with Tad Hamilton! is a fun, sweet, and genuinely moving film about love affecting the best version of one's self. Josh Duhamel plays the celebrity bad boy in trouble attempting to create a PR shift to clean up his image. He ends up falling for the small-town cutie who is nothing but herself, played by Kate Bosworth. As the bestie in question — Topher Grace — sulks in the corner, trying to convince his friend he's the best man for her, the film delivers a fun ride.
What Makes It Great
A scene-stealing Gary Cole co-stars as the silly but protective father of Bosworth's character, and popular performers like Nathan Lane, Kathryn Hahn, and Octavia Spencer round out the exceptional ensemble cast. Win a Date with Tad Hamilton! may not shy away from romantic cliches and a predictable plot, but the lead trio's engaging chemistry and Bosworth's delightful, scene-stealing performance helped elevate the warm and fuzzy flick and established it as a pleasurable viewing experience. Stream on Prime Video.
6 Sidewalks of New York
Edward Burns made a name for himself in Hollywood during the boom of independent cinema. Creating films of masculine camaraderie, tough love, and a particular brand of East Coast blue-collar machismo, Sidewalks of New York fits right into the Burns wheelhouse. The romantic dramedy chronicles the complicated dating lives of six dynamic Manhattan residents as their respective romances become interconnected with one another, yielding amusing and engrossing results.
What Makes It Memorable
Starring effervescent Brittany Murphy, a tough-as-nails Rosario Dawson, and, of course, Ed Burns, the film bounces from different corners of the five boroughs creating a triptych of romantic troubles and prosperity. Married couples and single people find love the hard way in a city brimming with possibilities. Burns utilized a documentary-style approach to the picture, interviewing the colorful characters and questioning them on their opinions on sex, romance, and love. Rent or buy on Apple TV+
5 Mr. Right (2016)
Mr. Right
- Release Date
- February 29, 2016
- Director
- Paco Cabezas
- Rating
- R
Sam Rockwell and Anna Kendrick were a match made in zany heaven when they appeared in the criminally underrated action romantic comedy Mr. Right, following the blossoming relationship between the hopeful and perpetually optimistic Martha McKay as she makes the shocking discovery that her handsome and quirky new beau, Francis Munch, is actually a lethal assassin who kills those who hire him instead of his intended targets. When Francis' shady past threatens their new romance, the pair team up to take down the bad guys.
What Makes It Memorable
Though it failed to make a splash at the box office, Mr. Right nonetheless capitalized on the lovable, offbeat energy of both Rockwell and Kendrick and the amusing, over-the-top humor in the film showcased their undeniable on-screen compatibility. Audiences watched with delight as Rockwell quite literally danced his way through violence, bullets, and bloodshed (while hilariously sporting a red nose), and his partnership with Kendrick was no doubt the rom-com's brightest moment. Rent or buy on Prime Video.
4 Plus One (2019)
If someone is prone to sulking, finds themself alone, and their search for the penultimate “one” has left them empty-handed, then a wedding may be the last place they want to end up. Such is the case for the two main characters Ben (Jack Quaid) and Alice (Maya Erskine), who both have recently gone through breakups and are also dealing with the burdensome expectation of getting married. So, the worst thing occurs when they are invited to an insufferable amount of weddings over four months.
What Makes It Memorable
The two happen to be best friends and decide the best way to endure the torture of going to a wedding alone is to be each other’s plus-ones, while also working to set the other up with romance. Plus One is a homerun and an outstanding addition to the romantic comedy genre, thriving because of its charismatic leads, sharp screenplay, and wildly amusing dialogue. Quaid and Erskine are phenomenal as the misfit odd couple Ben and Alice, who unsurprisingly end up falling for one another despite their noble intentions to do the exact opposite. Stream on Hulu.
3 They Came Together (2014)
A hilarious satire of romantic comedies that nails every joke and undercuts every expected beat of the formulaic nature that the worst of these films has to offer, They Came Together is near comedic perfection with an all-star cast making appearances at every corner. With Paul Rudd and Amy Poehler playing off each other like two jazz musicians finding music in every corner of their silly jokes, the film flies by on their coattails.
What Makes It Memorable
While some scenes nearly play like sketches, the likes of Bill Hader, Christopher Meloni, Keenan Thompson, and Ellie Kemper all assist in rounding out the bare-bones set-up into a skewering of the often fantastical nature of Hollywood romance. Upon its worldwide premiere at the Sundance Film Festival, They Came Together was awarded adoration and praise for director David Wain's exceptional usage of his epic cast and for effectively spoofing rom-coms in a complex and clever manner. Stream on Peacock.
2 Something New (2006)
something new
- Release Date
- January 29, 2006
- Director
- Sanaa Hamri
- Cast
- Sanaa Lathan , Fuzzy Fantabulous , Katharine Towne , Stanley DeSantis , K.C. Clyde , Wendy Raquel Robinson
- Rating
- PG-13
Sanaa Lathan, Simon Baker, and Mike Epps found themselves in a complex love triangle in Something New. It focuses on the successful, career-driven African-American woman Kenya McQueen as she struggles to fight her growing attraction to a handsome landscape architect Brian Kelly (Baker) after discovering he is white. When Kenya is set up with tax attorney Mark Harper (Epps), she is torn between the potential of her new relationship and her persistent feelings for Brian, the kind of man she didn't know she needed.
What Makes It Memorable
Something New addressed the topic of interracial relationships and provided an honest and insightful look at the intricate topic, and director Sanaa Hamri did an admirable job providing heartfelt commentary on the matter in her directorial debut. The rom-com was a modest financial success but earned appreciation from some critics, with Roger Ebert noting in his review, "By the end, Something New delivers all the usual pleasures of a love story, and something more. The movie respects its subject and characters, and is more complex about race than we could possibly expect." Stream on Starz.
1 Fever Pitch (2005)
The comic guile and brevity of Fever Pitch — a romance set against the Boston city as the Red Sox want on their historic World Series run — are strengthened by its two stars' charisma and chemistry. Starring Jimmy Fallon (in his only successful turn as a leading man) with the maximum comedic charm of Drew Barrymore, the two go on an unlikely road of love.
What Makes It Memorable
Hitting all the familiar beats of best friends trying to offer their romantic advice, meeting relatives, and one unusually odd tick that could drive the relationship apart, Fever Pitch is one of the best Beantown comedies. As Fallon plays the dedicated Boston fan whose all-encompassing devotion to a baseball team lands all the jokes it can before finally getting the romance to stick. Stream on Max.
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