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The romantic comedy genre has gone under much duress over the last few years since the streaming giants have taken over. Though 2022 was a sign in the right direction, with The Lost City grossing over $190 million and Ticket to Paradise taking in over $171 Million at the box office thanks to the star power of Julia Roberts and George Clooney, the genre still exists mainly in places like Netflix, Prime Video, and Peacock. Especially with studios leaning heavily on preexisting 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 curtails 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.
11 Enough Said
Before the light eventually burned out tragically on one of America's most significant screen presences, James Gandolfini shined 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. Enough Said has all the charm of a successful romantic comedy with enough character specifics thanks to its talented group of actors to create a winning premise.
10 The Heartbreak Kid
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 cohort Ben Stiller, The Heartbreak Kid saw the writer-director duo in similar terrain. 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, it turns out to be a nutcase that Stiller can't handle, and he finds love on their honeymoon. 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.
9 Sleeping With Other People
Leysle Headland has gone on to huge success with her highly popular Netflix show Russian Doll. But, before her huge success, she was on the indented scene making hilariously heartfelt and raunchy romantic comedies. Backed by a stellar pairing of Amanda Peet and Jason Sudekis, whose chemistry jumps off the screen. Also rounded out by a never creepier Adam Scott as he whirls Amanda Peet 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.
8 Blast From the Past
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. The chemistry between Fraser and Alicia Silverstone, who guides the naivety of the goofy Fraser, made for a silly and endearing romance. Especially in 1999, a year jam-packed with great films.
7 Definitely, Maybe
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. 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.
6 Two Can Play That Game
Finding a 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. With a knockout supporting cast including an improv-laden diatribe extraordinaire 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.
5 Win a Date With Tad Hamilton
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 yourself. 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 that 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. Especially a scene-stealing Gary Cole as the silly but protective father.
4 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. 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. As married couples and single people find love the hard way in a city brimming with possibilities.
3 Plus One
If you’re prone to sulking, find yourself alone, and your search for the penultimate “one” has left you empty-handed, then a wedding may be the last place you want to find yourself. Such is the case for our 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. 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.
2 They Came Together
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. While some scenes nearly play like sketches, the likes of Bill Hader, Christopher Meloni, Keenan Thompson, and Ellie Kemper all assist to round out the bare-bones set-up into a skewering of the often fantastical nature of Hollywood romance.
1 Fever Pitch
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. 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.