With Valentine’s Day upon us love is in the air…or the crushing belief that love will never come your way. It’s a holiday steeped in as much self-loathing as celebration but that’s why we love the movies, right? Because they give us the fantasy that helps us keep believing in love and romance. And with the release of Rebel Wilson’s new romantic comedy send-up, Isn’t It Romantic, just around the corner, let’s look at 14 essential romantic comedies that will help you restore your faith in love (or at least get you through the weekend). Please note, this isn’t a definitive list and hopefully this will act as a springboard for you to seek out other titles. 

1. It Happened One Night (1934)  

The era of the screwball comedy focused squarely on the wealthy, starting with this 1934 rom-com directed by Frank Capra. The film, which won multiple Oscars, follows reporter Peter Warne (Clark Gable) who plans to get the story of a lifetime by tracking heiress Ellen Andrews (Claudette Colbert). Ellen is hoping to get married in spite of her wealthy father’s riches but doesn’t know how the world works, leaving her to rely on Peter to get her where she needs to go. The film pokes fun at how spoiled and isolated the rich are – Ellen doesn’t understand how to dunk a doughnut or that people have to wait in lines – but also utilizes that classic rom-com trope: opposites attract. Gable and Colbert are fantastic, particularly during the scene where they have to playact as a married couple, arguments and all.  

2. Libeled Lady (1936)

An Academy Award Best Picture nominee in 1936, Libeled Lady is often considered by critics to be one of the funniest films ever made. I’m not sure about that, but if you’re talking an essential romantic comedy, it’s high on the list. Myrna Loy plays Connie Allenbury, another heiress à la It Happened One Night. But Connie is smart, and after a local newspaper publishes a lie about her she sues them for libel, to the consternation of the paper’s editor, Warren Haggerty (Spencer Tracy). Warren enlists the help of reporter Bill Chandler (William Powell) to seduce Connie in the hopes of proving the story true. It’s a comedic showcase for everyone involved, but particularly for Powell and Loy, who had previously made magic happen in the detective comedy The Thin Man in 1934. This was also a change of pace for Jean Harlow, who plays Warren’s frumpy, long-suffering fiancée, Gladys. Powell and Harlow were actually in a relationship at the time and their on-screen chemistry is just darling to watch for its authenticity.  

3. Bringing Up Baby (1938)

Katharine Hepburn and Cary Grant in 'Bringing Up Baby'

Katharine Hepburn and Cary Grant in ‘Bringing Up Baby’

So if you’re someone who didn’t think Libeled Lady was the funniest film ever made, then you’ll have to love Bringing Up Baby. (And if you love neither you don’t love romance or comedy, just saying.) This Howard Hawks-directed classic follows the rom-com formula to a T: two opposites come together for a series of high-concept hijinks. In this case, the two opposites are Katharine Hepburn as daffy heiress (was there any other kind back then?), Susan Vance, and Cary Grant as paleontologist David Huxley. The two are thrown together to hunt down one of David’s dinosaur bones that’s been stolen by Susan’s dog. Oh, and there’s a leopard named Baby. How does all this happen? Part of the fun is watching these two crazy characters comedically fall in love, so no spoilers from me!  

4. The Philadelphia Story (1940)

Katharine Hepburn might have been labeled box office poison but she was one of the early queens of the romantic comedy starting with Bringing Up Baby and continuing with The Philadelphia Story. Based on the Philip Barry play of the same name, Hepburn plays Tracy Lord, a blue-blood who’s just gotten out of one marriage and is rushing into a second. Leading up to the wedding Tracy’s ex-husband (played, once again, by Cary Grant) arrives, along with a reporter (James Stewart) to document everything. You’re probably getting sick of hearing about entitled snobs getting their comeuppance but they were a hot commodity leading up to WWII. Hepburn and Grant are so cool and graceful with each other that it’s no wonder they were paired up so often (I haven’t even mentioned 1938’s Holiday). Stewart has great comedic timing and his wooing of Hepburn will leave you swooning.  

5. I Married a Witch (1942)

Some of the most enduring romantic comedies have elements of the fantastical or supernatural within them, as is the case with I Married a Witch. Screen queen of the 1940s, Veronica Lake, plays Jennifer, a witch killed during the Salem witch trials. Before she died she cursed the Woolley family who condemned her to death. From that point on, all the men are doomed to bad marriages. When Jennifer is reincarnated she becomes hellbent on ruining the life of the most recent Wolley, Wallace (Fredric March). It’s said that Rene Clare’s romantic fantasy inspired another story about a man who falls for a witch: television’s Bewitched. Lake was never given her due as a comedienne and here she’s perfect as the vindictive Jennifer. Clare shows off the elegance and seduction of the fantasy with flying cars, banister sliding, and Veronica Lake stuffing waffles in her face. It’s said that the two leads absolutely hated working together, but you can’t really tell on screen. You believe Jennifer has bewitched him and that Wallace has fallen under her spell.   

6. Gentlemen Prefer Blondes (1953)

Jane Russell and Marilyn Monroe in 'Gentlemen Prefer Blondes'

Jane Russell and Marilyn Monroe in ‘Gentlemen Prefer Blondes’

Gentlemen Prefer Blondes isn’t just a romantic comedy about two couples getting together, it’s a romantic drama about the love that happens with friendship. In this case, the friendship between Dorothy Shaw and Lorelei Lee (Jane Russell and Marilyn Monroe, respectively). The two women end up on an ocean liner after Lorelei demands her boyfriend make a commitment to her. When Lorelei is brought up on charges of thievery – not helped by her gold-digging personality – it’ll be up to Dorothy to get her bestie out of the situation. There are so many moments that are hilarious throughout Gentlemen Prefer Blondes: from Dorothy’s thirsty crooning of “Is There Anyone Here for Love” to Lorelei’s interactions with a deep-voiced little boy traveling solo. Dorothy tries to resist the love of a private detective whose worst crime is that he’s poor, while Lorelei tries to get her milksop of a boyfriend to finally pop the question. There’s laughter, singing, and plenty of diamonds because, as Marilyn says, they’re a girl’s best friend! 

And now we move on to the more modern takes on romantic comedy…

7. Only You (1994)

In the 1950s romantic comedies added exotic locations to their bag of tricks. (I didn’t mention any on this list, but a great example is 1954’s Three Coins in a Fountain). Norman Jewison’s Only You takes the romantic aura of Rome and infuses it with elements relatable to the modern woman, or at least modern by ‘90s standards. Marisa Tomei plays Faith, a hopeless romantic who believes she’s destined to marry a man named Damon Bradley. The problem? She’s never met Damon. But when a chance encounter causes them to speak on the phone Faith hops on a plane to travel to Venice, Italy with her best friend Katie (Bonnie Hunt). Can a movie ever be bad if Bonnie Hunt’s in it? Her and Tomei exhibit the same sort of camaraderie seen in Gentlemen Prefer Blondes. Tomei, on her part, is paired up with Robert Downey Jr. and the two are fantastic making googly eyes at each other, telling the other how much they’re hated, and re-eancting Roman Holiday. It’s so romantic you’ll cry from how swoon-inducing it is. 

8. While You Were Sleeping (1995)

While You Were Sleeping hearkens back to the classic romantic comedies of the ‘40s, proof that the genre is timeless. Sandra Bullock got a Golden Globe nomination for her role as Lucy Moderatz, a token collector for the Chicago Transit Authority who spends her days dreaming about a man who rides the subway regularly – the problem is they’ve never spoken. When Lucy saves him from a group of muggers the man falls on the tracks and suffers a head injury, putting him into a coma. A stray line from Lucy as she’s leaving the hospital leads the man’s family to believe she’s his fiancée. It’s a premise ripped straight from the likes of Bringing Up Baby, and Sandra Bullock sells it. Her Lucy is a hopeless romantic alone in the world, and spending time with the new family gives her a sense of community while leading her to fall in love with the man’s brother (played by Bill Pullman).  

9. Clueless (1995)

Paul Rudd and Alicia Silverstone in 'Clueless'

Paul Rudd and Alicia Silverstone in ‘Clueless’

The teens have taken over the romantic comedy and it’s been successful ever since. In 1995 director Amy Heckerling adapted Jane Austen’s Emma for a modern, Noxema-using audience. Alicia Silverstone plays Cher, a seemingly vapid teenager attempting to play matchmaker for her teachers, an idea that ends up snowballing and affecting everyone she meets. It’s been amazing watching the romantic comedy transition from the older adults of the ‘30s and ‘40s into teenage dramas, and Cher’s plight is understandable. Her attempts to make everyone come from a good place (sometimes), but become out of control. A great L.A.-based story with a rocking soundtrack, I’m still a bit confused about Cher and Josh (Paul Rudd) getting together – they’re not blood, but they were raised together….and she’s 16 – but I’m all for a problematic fave.  

10. My Best Friend’s Wedding (1997)

My Best Friend’s Wedding is a rom-com where you’re not actually sure who to root for. The film tells the story of Julianne Potter (Julia Roberts) who’s stunned to hear her best friend, Michael (Dermot Mulroney) is getting married since the two made a promise to marry each other. Days before the wedding, Julianne realizes she truly is in love with her bestie, causing her to go to great lengths to stop the wedding. Julia Roberts is at her best playing a character who vacillates between romantic and vindictive. But the scene stealers are Rupert Everett and Cameron Diaz who are pure throwbacks to classic screwball characters. Cameron Diaz doing karaoke is just as fun to hear as Everett’s rendition of “Say a Little Prayer for You.”   

11. The Wedding Singer (1998)

Everything old is new again as we’re currently seeing, even the romantic comedy. This ‘80s throwback follows Adam Sandler’s Robbie Hart, a wedding singer left at the altar by his bride-to-be. The only one who stands by him is his co-worker, Julia (Drew Barrymore), sparking a romance between the two. We’ve been reading about a lot of lovelorn women, so The Wedding Singer immediately distinguishes itself by having a man in love with love. And, boy, does that lead to a lot of shenanigans. Nearly every line in this movie is quotable (“Julia Gulia!”) while all the while Sandler and Barrymore are creating a romantic duo on par with the likes of William Powell and Myrna Loy.   

12. 10 Things I Hate About You (1999)

Julia Stiles and Heath Ledger in '10 Things I Hate About You'

Julia Stiles and Heath Ledger in ’10 Things I Hate About You’

Similar to Clueless10 Things I Hate About You is an adaptation of Shakespeare’s The Taming of the Shrew, and let’s just say this movie’s depiction of women is a lot better than Bill’s was. Julia Stiles plays Kat Stratford, a notoriously difficult high schooler whose younger sister, Bianca (Larisa Oleynik) can’t date until Kat does. A series of events puts Kat in the sphere of bad boy Patrick (Heath Ledger) whose goal it is to get Kat to fall for him. Pretty much every teenage girl had an obsession with this movie in 1999. From Heath Ledger’s devil-may-care persona to Kat’s riot girl who doesn’t care what people think, the tone nailed the pop vibe of the ’90s. The script is incredibly witty and even works a few actual lines of Shakespeare in there. Not to mention it’s a powerhouse cast that broader audiences knew little about in 1999. (Yes, many a person actually wondered, “Who’s this Joseph Gordon-Levitt fellow?”) 

13. But I’m A Cheerleader (1999)

There are several romantic comedies about LGBTQ relationships, and I felt I should include one here. Jamie Babbitt’s But I’m a Cheerleader is criminally underseen and I’m desperate to change that. The film follows a naive teen named Megan (Natasha Lyonne) whose parents send her to a gay conversion camp. Megan is desperate to leave and asserts that she’s straight but can’t hide her growing attraction to a fellow camper, Graham (Clea Duvall). But I’m a Cheerleader takes the serious topic of gay conversion camps and lampoons it enough to make room for a sweet rom-com. Graham and Megan aren’t just interested in each other, they’re also interested in taking down the camp itself, led by Cathy Moriarty’s Mary and RuPaul’s Mike. One part dismantling the status quo and another part romantic comedy makes for a subversive good time.  

14. Crazy Rich Asians (2018)

The film that took 2018 by storm is an essential viewing if you’re blending your romance with drama. Constance Wu plays Rachel Chu, a professor traveling to Singapore with her boyfriend, Nick (Henry Golding). Rachel soon discovers Nick is wealthy, and as she acclimates to the world of Singapore high society she starts to clash with Nick’s mother, Eleanor (Michelle Yeoh). It’s weird watching this and not seeing comparisons to Bringing Up Baby. The opulence of Nick’s family coming up against Rachel’s average Jane, the emphasis on elegance and glamour, the bridging of humor and heart. Not to mention the movie actually retcons all the genre’s tropes by placing it in the hands of an all-Asian cast and director, giving us a unique twist on an old formula that made the whole genre feel fresh and new.

If you’re looking to keep the rom-com train going, Isn’t It Romantic is in theaters on February 13th! You can get your tickets here.


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