Cary Grant and Katharine Hepburn Movies

While many may prefer Katharine Hepburn opposite Spencer Tracy on-screen, there’s something special about the movies she made with Cary Grant. Cary Grant and Katharine Hepburn made four films together: Sylvia Scarlett (1935), Bringing Up Baby (1938), Holiday (1938), and The Philadelphia Story (1940).

The movies Grant and Hepburn made together are stunning. Their chemistry is dynamite, and their banting is so funny and enjoyable to watch. They’re definitely one of my favorite Old Hollywood pairings!

Below, I’ve ranked all four film collaborations the duo made together, from worst to best. Enjoy!

Cary Grant and Katharine Hepburn Movies, Ranked

4. Sylvia Scarlett (1935)

• Genre: Romance / Comedy / Drama
• Starring: Katharine Hepburn, Cary Grant, Brian Aherne, Edmund Gwenn
• Directed by: George Cukor

1st Grant-Hepburn Movie Ever Made

Listen, Sylvia Scarlett isn’t the worst movie ever made. It’s also not the best. Out of the four films Cary Grant and Katharine Hepburn made together, this one clearly comes in last place. However, if you’re a fan of this duo, or either one, then this very interesting movie is worth a watch!

Sylvia Scarlett follows a female con artist (Hepburn) who decides to help out her father and masquerade as a boy to escape the police, as well as freely move about society. Grant plays a smuggler who associates with them!

The best thing about this movie is the gender ambiguity of it all. It’s riveting, especially for the fact that it was made in 1935. If you’re interested in these types of stories, then definitely watch this film!

3. Holiday (1938)

• Genre: Romance / Comedy
• Starring: Katharine Hepburn, Cary Grant, Doris Nolan, Lew Ayres
• Directed by: George Cukor

3rd Grant-Hepburn Movie Ever Made 

Holiday is such (SUCH) a good movie. It’s crazy that it comes second to last on this list — but that’s just a testament to how great the other two movies are. This romantic comedy is so fun, and that’s mainly because of the wonderful chemistry that Cary Grant and Katharine Hepburn have.

In Holiday, Hepburn plays an unhappy wealthy young woman who ends up falling in love with her sister’s new, free-thinking, fiance (Grant). As Grant’s character struggles to adjust to his fiancee’s wealthy family, he also begins to realize that Hepburn’s character is the only one he truly enjoys being around. It’s grand fun.

Holiday is also a part of the Criterion Collection (spine #1009)!

Related — 6 Movies Similar to Holiday (1938)

2. Bringing Up Baby (1938)

• Genre: Comedy
• Starring: Cary Grant, Katharine Hepburn, Charles Ruggles
• Directed by: Howard Hawks

2nd Grant-Hepburn Movie Ever Made

Bringing Up Baby is one of the best screwball comedies ever made. It is absolutely delightful. It also happens to be one of the best Cary Grant and Katharine Hepburn movies ever. How could one not immediately fall in love with this amazing film?

Bringing Up Baby brings two polar opposite characters together: a flighty, hysterical socialite (Hepburn) and a serious, nerdy paleontologist (Grant). At first, both get on each other’s nerves. But when a leopard named Baby gets loose, the two stick together with each new hurdle sent their way.

Bringing Up Baby is also a part of the Criterion Collection (spine #1085)!

Related — Best Films From the 1930s: ‘Bringing Up Baby’

1. The Philadelphia Story (1940)

• Genre: Romance / Comedy
• Starring: Cary Grant, Katharine Hepburn, James Stewart, Ruth Hussey
• Directed by: George Cukor

4th (and Last!) Grant-Hepburn Movie Ever Made

The Philadelphia Story is the best Grant and Hepburn movie ever made. Really, it was quite hard to choose between the top three films on this list… but The Philadelphia Story is iconic. The dialogue is biting and hysterical — and when Grant and Hepburn act like they absolutely despise each other, it’s a joy to watch.

The Philadelphia Story opens as a socialite (Hepburn) prepares for her upcoming wedding… only two society reporters (Stewart and Hussey) crash the wedding for the inside scoop. Plus, her ex-husband (Grant) arrives for all the fun. It’s a joy to watch. An absolute joy.

The Philadelphia Story is also a part of the Criterion Collection (spine #901)!

Related — The Best Movies From the 1940s: ‘The Philadelphia Story’ (1940)

What’s Your Favorite Grant-Hepburn Collaboration?

Alright, now we want to hear from you! What’s your go-to Cary Grant and Katharine Hepburn movie collaboration? This list is a great list of comfort movies, isn’t it? Hit the comments below with all your thoughts and opinions!