All 4 Cary Grant & Katharine Hepburn Movies, Ranked Worst To Best

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All 4 Cary Grant & Katharine Hepburn Movies, Ranked Worst To Best
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Mary Kassel is a Senior Lists Writer at Screen Rant and a contributor to the site's Reviews section as well. Kassel studied film and television in college and emphasizes theory and analysis in their work. Additionally, they focus this analysis on intersectionality and the experience of artists from all walks of life.

It's difficult to determine who the most famous stars in Hollywood history are, but Cary Grant and Katharine Hepburn are undoubtedly on the list. Like most actors of their generation, Grant and Hepburn partnered on several projects throughout their career, four total, as the studio executives took notice of their onscreen chemistry.

Throughout their careers, the actors were highlighted for their strengths and weren't defined by their costars. Cary Grant's best movies with Alfred Hitchcock show that he had chemistry with almost anyone he worked with. However, the fact that both Hepburn and Grant were forces of nature on their own meant the dynamic of their characters was often approached through a more contemporary lens. The women Hepburn played weren't secondary to Grant's characters.

There are also compelling themes of gender role reversal, even if the movie is first and foremost a comedy. 3 Sylvia Scarlett Directed by George Cukor Probably the least well-remembered of all of Grant and Hepburn's collaborations, Sylvia Scarlett was revolutionary for its time. It revolves around Hepburn's character, Sylvia Scarlett, who dresses as a boy to accompany her father on his clandestine journey across Europe. This gender-bending performance has roots in the theater and isn't an uncommon trope in older romantic comedies.

2 Holiday Directed by George Cukor The same year as Bringing Up Baby, Hepburn and Grant reunited with the director of Sylvia Scarlett for a more straightforward rom-com, Holiday. Holiday focuses on the differences in wants and aspirations between social classes, as Grant's character, Johnny, is about to marry into a wealthy family with high expectations, but he wants to travel the world and discover what he wants out of his life.

Critics were much more interested in Holiday than audiences, and this is why it's not as famous as other collaborations between Hepburn and Grant. It's no wonder that Holiday would appeal to cinephiles, as the central thrust of the plot is about imagining a better world and exploring creative possibilities. Grant and Hepburn are sweet and charming throughout the film, capitalizing on their physical chemistry with comedic stunt work.

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