The Rom-Com Hall of Fame (According to a Millennial Knuckle Dragger)
When you can’t take five steps into a CVS Pharmacy without seeing endless tunnels of heart-shaped Valentine grams, that can only mean one thing: it’s rom-com season once again. To many of us, Valentine’s Day is traditionally a time to celebrate the ones that we love by splurging for chocolates, flowers, and cozying up to a movie that probably doesn’t involve Vin Diesel.
Historically, romantic comedies are one of the more misunderstood subgenres in mainstream moviegoing. Given how much corny material has been made, it’s easy to fall into the assumption that they’re all just love stories with played-out humor and a happy ending that fades out on a wide shot of a city and a pop song by Natasha Beddingfield.
That can be true in some cases, but many of them are nuanced in ways that we don’t quite articulate on first or even second viewing. The most universally embraced rom-coms have a distinct charm, an effervescence that makes them enjoyable to watch many years later, regardless of gender. This Valentine’s Day, if your significant other would rather avoid being dragged to see Jackass Forever, here’s a curated list of rom-coms that anyone with a working pulse can enjoy.
10. High Fidelity (2000) - dir. Stephen Frears
There are tons of romantic comedies told from the perspective of men; far too many are written with an unrealistic charm that isn’t always reminiscent of real people. The movie adaptation of Nick Hornby’s best-seller High Fidelity is a playful, candid exploration of the modern male identity disguised as an offbeat romantic comedy. Love is viewed as something foreign through the eyes of an underachieving music snob (John Cusack) who tries to get his ex back while simultaneously reflecting on the ghosts of relationships past.
The enduring power of High Fidelity isn’t grand romance, but rather its eclectic soundtrack and honest evaluation of accountability in relationships. Our protagonist Rob isn’t the sweep-you-off-your-feet type—he’s actually kind of a jerk. He’s a narcissist, egocentric, and crippled by his inability to take ownership of his actions. Rob must undergo a journey of self-discovery to find the error of his ways and learn how to properly commit.
Available for rent on Amazon Prime
9. About Time (2013) - dir. Richard Curtis
Written and directed by Richard Curtis, About Time feels special in that it functions on two fundamental levels: a love story of guy meets girl and a love story between father and son. Both elements converge in this sci-fi/rom-com with a sophistication and depth that will reduce even the most callous of viewers to a fleshy puddle of wailing vulnerability.
It tells the story of Tim and Mary (Domnhall Gleeson and Rachel McAdams), a picturesque couple save for one small wrinkle: Tim can travel backward in time—a trait passed down from his aging father (Bill Nighy). Through Tim’s prolonged hijinks of trying to perfect his journey in love, he learns an important lesson on letting go of the past to make room for his future. Despite the minor imperfections of its time travel mechanism, About Time upends the stale tropes of an exhausted genre to create something wholesome and fresh. Just get your Kleenex ready and don’t say I didn’t warn you.
Available for instant streaming on Netflix
8. The Wedding Singer (1998) - dir. Frank Coraci
Just a few years after his stint as a mainstay cast member on Saturday Night Live, Adam Sandler threw it back to 1985 with The Wedding Singer, a sweet and silly musical comedy about a mild-mannered romantic who falls for an engaged young woman (Drew Barrymore) after his fiance leaves him heartbroken at the altar. From Spandau Ballet to the tri-color shirts and a surprise cameo from Billy Idol, this rom-com classic radiates with a glorious mid-80s gleam.
In typical fashion, Sandler enlists the help of Happy Madison regulars Allen Covert, Kevin Nealon, Steve Buscemi, and Peter Dante to round out his zany lineup of side characters. Most notable of which is the film’s archnemesis in Matthew Glave as the cartoonishly despicable Glenn Gulia. Sporting a flamingo-pink shirt and a blinding white blazer, Glenn is the undisputed king of punchable faces and the foremost profile on the Mount Rushmore of dirtbag movie boyfriends.
Available for instant streaming on HBO Max
7. Hitch (2005) - dir. Andy Tennant
Though the tide has begun to turn in recent years, there’s been an obvious lack of colored representation in mainstream romantic comedies since the dawn of the artform. From Just Wright to Think Like a Man, most rom-coms with colored leads generally tend to target a specified demographic. In 2005, this cultural barrier proved no challenge for Will Smith, the Philly-born superstar whose accolades continue to speak for themselves, which includes a Best Actor nomination for his most recent work on King Richard.
After Bel Air but long before he showed Venus and Serena how to perfect their backhand, Will was pining for the affections of Eva Mendes in Hitch, a self-produced film featuring colored leads that achieved mainstream recognition and global box office success. There’s a universal magnetism to Will Smith and Eva Mendes’ personalities that seemed to eclipse any perceived notions of skin color. Their onscreen pairing was a celebration of multi-culturalism in the mainstream sense that helped pave the way for a new generation of color diversity in rom-coms that is much more ubiquitous today.
Available for instant streaming on Hulu and Peacock
6. Singin’ In The Rain (1952) - dir. Gene Kelly and Stanley Donen
Even for audiences who aren’t into classic cinema, Stanley Donen’s Golden Age opus has cultural reverence as an ageless rom-com with an enduring legacy that transcends age or gender. This delightful and timeless musical examines the labored transition from the silent film era to talkie cinema, which chronicles a blooming dynamic between the incumbent superstar (Gene Kelly) and a rising talent (Debbie Reynolds).
Co-directed by its leading man, who also served as principal choreographer, Singin’ In The Rain is a kaleidoscopic explosion of song, dance, color, and verve. A charming dalliance unfolds between the silent film star and a young starlet named Kathy Selden, the spunky but talented love interest. The iconic duo and their palpable chemistry helped establish blueprints for a genre whose sole aim is to make audiences smile about love.
Available for instant streaming on HBO Max
5. When Harry Met Sally (1989) - dir. Rob Reiner
The chemistry between a movie’s creative components are just as important than that of its performers. In the 32 years since its release, When Harry Met Sally only grows in the estimation as a delightful rom-com with wit, charm, and brains to boot. All credit due to the creative synergy between its director Rob Reiner and luminous screenwriter Nora Ephron; the resulting balance is a teeter-totter that explores the primitive divide between men and women with sharp and lucid perception.
The film is the preeminent example of “will they or won’t they” between Sally (Meg Ryan) and Harry (Billy Crystal), platonic friends who pass like ships in the night over the course of many years. Set to a robust, big band swoon from Harry Connick Jr., When Harry Met Sally is a hall-of-fame entry that explores the collision of gender dynamics in a way that still feels funny but truthful over three decades later.
Available for instant streaming on HBO Max
4. There’s Something About Mary (1998) - dir. The Farrelly Brothers
As the filmmakers responsible for Dumb & Dumber and Kingpin, The Farrelly Brothers had a comedic sensibility that loomed large over the nineties. In a decade ruled by entertainment on a massive visual scale, the Farrellys proved that humor can still thrive without a sinking ship or Tyrannosaurus Rex. There’s Something About Mary was one of the highest-grossing films of the year and a benchmark for the R-rated comedy boom of the forthcoming decade.
Starring Ben Stiller as the docile protagonist Ted, a man who gets another chance with the girl who got away (Cameron Diaz), the movie laid the foundation for romantic comedies with raunchy humor but a heart of gold. Much like Judd Apatow’s work in the mid-2000s, There’s Something About Mary was a humanitarian drama with absurdist hilarity. It functions as a story about being true to oneself, but is generally remembered for Cameron Diaz putting ejaculate in her hair. It was the ushering of a brave new era in comedy, one whose boundless audacity is almost completely extinct in movies today.
Available for rent on Amazon Prime and Vudu
3. 10 Things I Hate About You (1999) - dir. Gil Junger
Teen culture in the late nineties hasn’t aged particularly well in many respects. From the music we consumed to the clothes we wore, so many facets are now considered relics from a bygone era—but not 10 Things I Hate About You. This beloved classic is widely recognized as a milestone of high school rom-coms with a fantastic cast, smartly written script, and a looming influence still felt over 20 years later.
It makes the most of an iconic pairing between the independent-minded Kat Stratford (Julia Stiles) and bad boy Patrick Verona (Heath Ledger). The dichotomy they share still reverberates to this day in any teen comedy where its characters seem precocious with the agency to think for themselves. Rounded out by a tremendous supporting cast in Joseph Gordon Levitt, David Krumholtz, Gabrielle Union and Allison Janney, 10 Things I Hate About You was an emblematic milestone for teenage representation in movies.
Available for instant streaming on Disney Plus
2. Shaun of the Dead (2004) - dir. Edgar Wright
A case can be made that of all the great duos we’ve covered, the superlative isn’t two people but rather two genres. British filmmaker and devout cinephile Edgar Wright burst onto the scene with an instant classic that drew considerable influence from cult movies past. Finding inspiration from the work of George A. Romero, Wright blazed a name for himself in contemporary cinema by crafting one of the most celebrated films of the 21st Century in Shaun of the Dead, a zombie rom-com for people who love zombies and rom-coms.
Shaun of the Dead follows a slacker’s (Simon Pegg) fight to survive when an army of the undead wreaks havoc on London. To this day, the movie remains immensely popular with genre fans who recognize its clever and nuanced execution. Being a huge fan of movies himself, Edgar Wright constructed this film as a loving homage to the carnivorous subgenre. But at the heart of this apocalyptic zombie saga, it still manages to connect with audiences through its manchild protagonist and his wayward struggle to get his act together—or risk losing Liz (Kate Ashfield), the woman of his dreams.
Available for rent on Amazon Prime or Vudu
1. The Princess Bride (1987) - dir. Rob Reiner
There are many reasons why The Princess Bride still resonates as a cherished cult classic. For one, it’s incredibly quotable, much to the credit of its screenplay by the legendary William Goldman. Secondly, audiences love the simplicity of its plot—a swashbuckling adventure that outlines a storybook romance between Princess Buttercup (Robin Wright) and the brave farmhand Westley (Cary Elwes) and the lengths he’ll go to rescue her from the clutches of evil.
What differentiates The Princess Bride from the rest of the rabble is the sheer creativity of its execution. Rob Reiner’s fantasy world is fueled by imaginative, childlike wonder with adoring characters who speak in distinguished voices. With a colorful supporting cast that includes Wallace Shawn, Andre the Giant, Fred Savage, and Christopher Guest, this classic bursts at the seams with uncontrollable originality. Even outside the boundaries of romantic comedy, The Princess Bride stands on its own as a must-see for all ages and genders.