With the recent release of Set It Up on Netflix, film fans are asking, “Has the romantic comedy returned?” The genre that dominated the 1990s, the rom-com has suffered of late due to the glut of comic book movies, franchises, and the male-dominated belief that only women watch these movies. (It also helps that Sleepless in Seattle, the film many cite as the best rom-com ever, turned 25 yesterday.) Here are the Dames’ top 5 favorite romantic comedies.
A confession: I never got on the romantic comedy bandwagon. Sure, I’ve seen nearly everything oft-considered representative of the genre, but I never had the deep connection to works like While You Were Sleeping and You’ve Got Mail that other girls my age did. That was probably because I was off letching over Jeremy Irons movies or something, not really sure. Either way, my list goes for the more classical sensibilities of where the genre started – with one movie I just had to include.
Libeled Lady (1936)
Libeled Lady is one of those films I wish I could live in, if only to hang out with the amazing cast assembled. The story follows a newspaper reporter named Bill Chandler (played by the dashing William Powell) tasked with seducing an heiress (Myrna Loy) pushing a libel suit against the paper. The chemistry between Loy and Powell is always evident, whether or not they were playing in Thin Man movies. For me, though, the true hilarity and romance is found in the B-plot between Powell and Jean Harlow as the “mousy” and “nagging” Gladys. Gladys has to pretend to be Bill’s wife in order to “prove” the libel suit and this means putting the two in a hotel room despite the fact their characters can’t stand each other. Powell and Harlow have wonderful comedic timing – some of their insults to each other are just as hilarious as they are mean – and phenomenal chemistry, no surprise considering they were lovers. Ironically, Harlow’s story is all about how her fiance, played by Spencer Tracy, won’t marry her, yet in reality it was Powell who wouldn’t marry Harlow. I actually get mad that Harlow gets stuck with Tracy at the end. Her and Bill should have gone off into the sunset together.
Bringing Up Baby (1938)
Bringing Up Baby shows up twice on this list and it should because it’s the best thing ever! Subversive, quick-witted, with some of the most talented performers you’re like to see in cinema, past or present. The film has the mother-of-all high concept premises involving an archaeologist (played by Cary Grant), a dinosaur bone, a daffy heiress played by Katharine Hepburn (were there any others back in the day?), and a leopard. I don’t think Hepburn and Grant have quite the chemistry Libeled Lady does so I tend to consider it more a comedy than a romance, but Lauren included it so that means I can too!
Only You (1994)
Here’s one of those ’90s rom-coms you love so much. I think I love Only You because it adheres and reveres the classic movie tradition with its story of Faith (Marisa Tomei) who goes to Italy in search of a man she believes to be her soulmate. There’s an extended moment where Faith and her best friend, played by everyone’s “mom,” Bonnie Hunt, watch Enzio Pinza perform South Pacific and even though I didn’t know that as an adult, I understood Faith was like me. Tomei and Hunt are hilarious while they embark on this manic adventure, but the movie really picks up once Robert Downey Jr.’s character arrives. I know he was probably high as hell when he made this, but him and Tomei are fantastic! I actually included the scene where they re-enact Roman Holiday’s “Mouth of Truth” scene on a list of sexiest movie moments. Oh, and let’s not forget Billy Zane is in this and he’s awesome.
Some Like It Hot (1959)
Speaking of sexy, who doesn’t love Some Like It Hot? It’s romantic, it’s comedic, it’s easily one of the gayest straight movies to come out of the ’50s. I know everyone goes on about the relationship between the characters played by Tony Curtis and Marilyn Monroe, but we know the real rom-com goodness is found in the love between Jack Lemmon’s Daphne and Joe E. Brown’s Osgood. I mean, we all know every good romantic comedy starts with characters who are opposites, and this entire relationship lives up to the word. And yet for their whole “opposites attract” dynamic, Osgood is willing to do whatever is necessary to secure Daphne’s love, adopt children, take up smoking, and change his sexual preference! That’s love right there.
The Wedding Singer (1998)
This was a last minute addition and I can’t believe I forgot it. I quote The Wedding Singer profusely because it’s got great dialogue, but it’s also Adam Sandler and Drew Barrymore at their comedic best. I’m not saying this would be my de facto proposal, but you can’t go wrong finding a man who can sing to you AND bring you Billy Idol.
I love me a good romantic comedy. A good one. There are so many that just aren’t. But when the good ones hit, I can watch them forever and ever. It’s tough to narrow it down to only five, and yeah, I’ll admit that all of these came out during my lifetime. But these really are the ones that I can always turn on, anytime of the day or night.
When Harry Met Sally (1989)
No one can ever dissuade me. When Harry Met Sally is the greatest romantic comedy of all time. With characters we can relate to, but aren’t carbon copies of people we really know. Fantastic dialogue. This whole element of wondering how these crazy kids will ever figure out that they’re perfect for each other. The frequent references to Casablanca, which is not a comedy but is one of the best romance stories of all time. Meg Ryan is charming. Funny, perfect supporting performances from both Carrie Fisher and Bruno Kirby (RIP). And Billy Crystal’s Harry gets to utter one of the most perfect romantic lines ever written.
The Wedding Singer (1998)
I LOVE The Wedding Singer. It embraces everything that was awesome about the 80s, with one of my favorite soundtracks of all time. It’s hilarious, and sweet, and nostalgic, and immensely quotable. Plus Adam Sandler and Drew Barrymore are just so freaking cute. This is the best comedy either of them have ever done. And a rapping granny? And Billy Idol? What’s not to love?
While You Were Sleeping (1995)
What’s funny about this movie is that, well, who hasn’t imagined a romance with someone they don’t know? This takes that idea and turns it into a full blown tale of misunderstanding, a little bit of innocent fibbing, and one of the funniest movie families ever. Sandra Bullock is charming and sweet and was clearly destined to be a huge star. Bill Pullman was charming, not so sweet, but dang cute. And Joe Jr.? Well, I hope he found happiness along the way.
Sleepless in Seattle (1993)
Did you know this movie was nominated for two Academy Awards? And it should have. The second of three films to star Meg Ryan and Tom Hanks together. What’s fascinating is that they only appear in three scenes together, only one of which involves them having an actual conversation. They never kiss. They never even hold hands. And yet, it’s so romantic. I adore the references to An Affair to Remember, especially The Scene with Rita Wilson, Tom Hanks, and Victor Garbor. Then Rosie O’Donnell says one of the most accurate lines in any rom-com: “You don’t want to be in love. You want to be in love in a movie.” There are no truer words.
Love Actually (2003)
It’s no secret that I love Love Actually. It’s full of problems, sure. But my very favorite thing about it is the couple right up there. Colin Firth and Lucia Moniz are so cute as they both fall in love with each other without even being able to have a conversation. And then he learns Portuguese so he can go back and propose and then she learned English “just in cases”?? It’s so great. I do. I cry every time and I’m not ashamed. I also really love the unfolding relationship with Hugh Grant and Martine McCutcheon. And then there’s Liam Neeson who is still grieving his wife, and loves her so much that he’s raising his step-son. There are problems, yes. But it is still such a sweet movie that I’ll never hate it.
Bringing Up Baby (1938)
It’s seen as the quintessential screwball comedy now, but Bringing Up Baby was not particularly popular back when it was released. That’s a shame, because it has way more than just the central romance between Cary Grant and Katherine Hepburn to recommend it. There are dogs and pet leopards and weird psychiatrists and the intercostal clavicle of a brontosaurus. There’s Cary Grant in a fluffy negligee. But since we’re talking rom-coms, let us note that the entirety of Bringing Up Baby hinges on Kate Hepburn’s Susan doing everything in her power to get to know Grant’s David, up to and including stealing all his clothes before getting him arrested. That’s true love, right there.
Much Ado About Nothing (1993)
When we talk romantic comedies, let’s return to one of the originals and credit William Shakespeare. Much Ado About Nothing is one of Shakespeare’s funniest plays and the 1993 film is certainly Kenneth Branagh’s best adaptation, turning on mistaken identities, love discovered, and the very just punishment of some slut-shamers. Much of the film’s charm is a result of the stellar cast, including Branagh, Emma Thompson, Kate Beckinsale, and Michael Keaton, who can handle the language and the humor without breaking a sweat. The effervescence of this film is just amazing – every frame brims with energy and light and wine-infused hijinks. And although their real-life romance didn’t end so well, Branagh and Thompson are still the perfect Benedick and Beatrice.
It Happened One Night (1934)
It Happened One Night hits all of the requisite romantic comedy tropes – a woman in love with the “wrong” man meets the right one on a cross-country road trip, they bicker, battle, and even do the whole “fake married/have to sleep in the same room” bit so popular in fan fiction. It doesn’t hurt that both Colbert and Gable have excellent chemistry and comedic timing—their fake married scene is just hilarious. It defined the screwball genre, and It Happened One Night is still one of the best romantic comedies ever made.
The Gay Divorcee (1934)
The Gay Divorcee is my favorite Astaire/Rogers romantic comedy, not least because it spends as much time on the comedy of errors as it does on the dancing. Both leads are in excellent form here, chasing each other around a totally unrecognizable version of Brighton. And the secondary characters are among the best, with Edward Everett Horton and Eric Blore lending their formidable comedic talents to a silly and massively enjoyable musical. But The Gay Divorcee also reminds us that Astaire and Rogers can do a combo of passion and humor, as they breathlessly dance to “Night and Day,” and then follow things up with an extended comedy sequence that pushes the limits of the Code.
Some Like It Hot (1959)
Yes, Marilyn Monroe is glorious in this, and so is Tony Curtis’s Cary Grant impression, but let us discuss Joe E. Brown’s epic romance with Jack Lemmon. Some Like It Hot pushed the boundaries so far that one wonders how Wilder got away with it, spending almost as much time chronicling the romance between two men as he did the more heteronormative couple. When Jerry realizes that he’s actually going to have break Oswald’s heart, it’s real regret. And the ending is still one for the ages – Oswald really doesn’t care about Daphne’s gender. He just wants Daphne.
10 Things I Hate About You (1999)
When I think about my teen years, I indelibly come back to this movie. As a child of the ’90s, this is my ideal teen movie and a sweet romance. I love Julia Stiles as Kat; I wanted to be Kat when I saw this and I still want to be Julia Stiles when I grow up. The movie has a delightful (then) up-and-coming young cast as well as a fun and talented group of adults. Holding everything together is the rich chemistry shared between Ledger and Stiles. Check this one out if you haven’t.
Notting Hill (1999)
Yes, I was an anglophile kid in the 1990s and as such there was a lot of Hugh Grant in my life. My ’90s was Four Weddings and a Funeral and Notting Hill. I was all about Notting Hill when it came out. Heck, I’ll still watch it when I stumble on it. The film shows both actors at their peak, doing what they do best and they have a very sweet chemistry.
While You Were Sleeping (1995)
This movie feels like a bit of an outlier in this list since it doesn’t involve teenagers or Hugh Grant. However, there’s one thing this movie has: Bill freakin’ Pullman. My 1994-1997 was all about Bill Pullman. This movie is ridiculously adorable from Sandra Bullock showing just why her career hit (and held) the popularity she has, to her absolutely saccharine chemistry with Bill Pullman. I dare you to not like this movie.
Pretty in Pink (1986)
I’ll admit it, I’m Team Blaine (okay, and occasionally Team Spader). While the eighties are very much my weak decade, this movie has been a favorite of mine since watching it in high-school. The sweetness of the entire cast (and Andrew McCarthy’s smile) completely pull me in. They’re so gosh darn likeable. This is probably the cutest of the “Brat Pack” movies and is definitely my favorite.
Love Actually (2003)
I’ve written about the delightfulness of Love Actually extensively for this site already. Everything about this movie warms the cold depths of my heart and even more than fifteen years later, it is still a go-to viewing for me.