If you’re looking for movies similar to the classic, romantic comedy Holiday (1938), then look no further. Here, you’ll find a selection of films that retain the same delightful feel as Holiday while also providing their own unique perspectives. All these movies feature Katharine Hepburn and Cary Grant in some capacity, but rather than simply being ‘Hepburn-and-Grant films’, they are each truly special on their own terms.
What sets Holiday apart from other romantic comedies is its lighthearted tone combined with timely social issues. So, the films listed here all take this concept and create something special of their own. Unlike Philadelphia Story, which has its characters sparring until the very end, the movies listed below focus on two people who are surprisingly alike and whose quirkiness brings them together. They truly seem to understand each other, which leads to an enjoyable appreciation of their partnership.
When you read the recommendations, hopefully, it all makes sense! Keep reading to find the best movies similar to Holiday!
Bringing Up Baby (1938)
Starring: Cary Grant and Katharine Hepburn
Also from the same year as Holiday, Bringing Up Baby follows a straitlaced archeologist (Grant) who is attempting to secure a $1 million donation to his museum, only to consistently be pulled into the crazy scheme after a crazy scheme by a flighty heiress (Hepburn) and her pet leopard, Baby. Directed by Howard Hawks, Bringing Up Baby is a classic screwball comedy that is so much fun to watch.
Why It’s Similar to Holiday: Cary Grant and Katharine Hepburn are at it again in Bringing Up Baby. While their two characters don’t immediately get along as they do in Holiday, the friendship (and later, romance) becomes apparent soon enough in the movie, making for a wacky ride that it seems only Grant and Hepburn can really pull off. Much like Holiday, Bringing Up Baby is lighthearted fun, and cute as can be. If you want zingers that pull at the heartstrings, watch The Philadelphia Story. If you want a cute rom-com, watch Holiday or Bringing Up Baby.
My Favorite Wife (1940)
Starring: Cary Grant and Irene Dunne
Cary Grant and Irene Dunne were great together — which is evident in My Favorite Wife. The movie follows a shipwrecked woman, who is rescued after seven years of living on an island, who returns home to find that her husband married another woman earlier that day. There’s no doubt in the husband’s mind that his first wife is the one for him… but that doesn’t mean there’s not an awful lot of fun drama the duo goes through as he tries to break the news to his new wife.
Why It’s Similar to Holiday: My Favorite Wife is similar to Holiday in many ways. While in this movie the featured couple is already married, the pair have a lot of hysterical drama. But through it all, they both know that they love each other. Grant and Dunne bounce off each other well — and if you feel like there were romantic moments missing in Holiday, you won’t be disappointed with My Favorite Wife.
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The Awful Truth (1937)
Starring: Cary Grant, Irene Dunne, and Ralph Bellamy
The Awful Truth follows a fighting couple who decide to divorce early on in the film because they both believe they’re cheating on each other. However, as they begin to date other people, they find themselves going out of their way to ruin the other’s happiness. In the end, they finally realize what the audience knew all along: they love each other and are made for each other.
Why It’s Similar to Holiday: The Awful Truth has a whole lot more drama and fighting than the main couple in Holiday does. However, both of the movies have the same vibe, if you will. The main reason The Awful Truth ended up on this list is because of the extent Irene Dunne’s character goes to ruin Cary Grant’s new relationship. It’s awful fun and feels very much like the characters in Holiday, even if the characters are pretty straight-laced here.
His Girl Friday (1940)
Starring: Cary Grant, Rosalind Russell, and Ralph Bellamy
Yet another Grant film. I can’t help it! His Girl Friday is one of the best screwball comedies to come out of Old Hollywood and I’m very happy it’s still beloved to this day. The movie follows a newspaper editor (Grant) who tries everything he can to get his ex-wife (Russell) to not marry her new boyfriend… and to come back to the newspaper business. The movie talks a mile a minute, the dialogue is phenomenal, and the characters are half straight, half crazy. It’s a good time.
Why It’s Similar to Holiday: His Girl Friday is fast-paced and full of fights between the main characters. However, it’s on this list because, despite how much the main couple “hates” each other, they are alike. They’re one and the same. And when they finally realize this, it’s a delight to watch them bounce off of each other. His Girl Friday is similar to Holiday in this regard, as the main two characters really are offbeat and fun, just like in Holiday!
The Thin Man (1934)
Starring: William Powell and Myrna Loy
Nick and Nora Charles are one of the best couples in an Old Hollywood movie. The Thin Man introduced them to the world. The movie follows retired detective Nick Charles (Powell) as he’s basically forced to solve a disappearance and murder, all while his equally as fun wife Nora (Loy) is by his side. The Thin Man is perfect for those who want a little bit of romance dashed with a little bit of murder.
Why It’s Similar to Holiday: The Thin Man is probably one of the best movies similar to Holiday, as the main couple in both movies seamlessly bounces off of each other in an offbeat, interesting way. Both couples enjoy being around each other. They like talking to each other. They’re not fighting, not acting as if they don’t love each other. It’s a delight to see and still fun to watch — and both movies are adorable.
My Best Friend’s Wedding (1997)
Starring: Julia Roberts, Dermot Mulroney, Cameron Diaz, and Rupert Everett
My Best Friend’s Wedding follows a food critic (Roberts) who freaks out upon hearing that her best friend (Mulroney) is going to marry a young college student (Diaz). Wanting him all to herself and convinced that she loves him, she sets out to break up the relationship before the wedding and confess her love to her best friend. Chaos, of course, is everywhere in this film. And it’s a delight.
Why It’s Similar to Holiday: Okay, hear me out on this one. Yes, it’s not an Old Hollywood romcom. But My Best Friend’s Wedding also has a woman longing for her love (who’s happily with someone else). The movie also has wonderfully funny moments between the main couple, even though they’re not together. The movie also has a group of friends (I’m mainly talking about Julia Roberts and Rupert Everett’s characters’ friendship) that is oh so fun to watch when they’re together. Holiday and My Best Friend’s Wedding may be somewhat different… but I feel like if you like the whole romantic angle of Holiday, you’ll like My Best Friend’s Wedding, too.