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. Though the popularity and success of these movies varied when they were released, all of them are known as classics and are highly influential in modern-day cinema. While most of these films cast the actors as a romantic couple, their shared comedic timing is what stands apart.

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.

Many of Katharine Hepburn's best movies were part of a collaboration with Grant, as both of their stars rose around the same time. This allowed the pair to work on similar projects as audiences were eager to see them individually but even more excited to watch them work together. All of their projects are from the early part of their careers, as their last film together, The Philadelphia Story, was released in 1940. However, the late 1930s were an interesting time for film, and the narratives behind their work pushed boundaries in unexpected ways.

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. They were just as important and enjoyed equal levels of respect and importance onscreen. Additionally, they each demonstrated the ability to deliver sharp-witted dialogue with ease.

4 Bringing Up Baby (1938)

Directed by Howard Hawks

Bringing Up Baby and other classic screwball comedies from the early days of Hollywood paved the way for the best enemies-to-lovers rom-com movies of the modern day. Rom-coms, in general, owe a lot to screwball comedies and amazing acting duos like Hepburn and Grant. In the film, Grant plays David Huxley, a paleontologist who gets swept away by the chaotic life of Susan Vance (Hepburn), who's fallen in love with him. Throughout the film, David tries not to be charmed by the devil may care attitude of Susan, but it's impossible for him and for the audience.

There are also compelling themes of gender role reversal, even if the movie is first and foremost a comedy.

There are also compelling themes of gender role reversal, even if the movie is, first and foremost, a comedy. For a long time, Hollywood considered Bringing Up Baby a major misstep, and it was a box office bomb at the time of its release. Time has been kind to Bringing Up Baby, and the critical reception to the film has warmed considerably, as it's considered a classic by contemporary standards. Part of the reason that Bringing Up Baby was so different from other romance movies of the time is that it was far less concerned with realism than with entertainment.

It's fair to say that the madcap plotting and improbable storyline might put off some audiences, but viewing Bringing Up Baby through an absurdist lens is a way to see past the silliness. Unlike their other collaborations, Bringing Up Baby isn't as in conversation with relevant social and political issues and doesn't push cultural boundaries as some other works. However, this doesn't change the fact that Bringing Up Baby is pure fun and doesn't waste a moment. Every minute is chock-full of jokes and physical comedy that modern comedies emulate.

3 Sylvia Scarlett (1935)

Directed by George Cukor

Probably the least well-ed 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. However, for film in the 1930s, it was quite boundary-pushing. Tonally, Sylvia Scarlett is a bit all over the place, as there are moments of comedy, but there are also dark aspects of the script, with deaths and betrayals.

Sylvia Scarlett was the first movie Hepburn and Grant worked on together. Though it's not as seamless and familiar as their later work, it's incredible to see their bond developing onscreen. Surprisingly, though it's a romance, Hepburn and Grant don't end up together by the end of Sylvia Scarlett. Sylvia's true love interest, Michael, is played by Brian Aherne. However, it's obvious that Grant and Hepburn have superior chemistry, and most of their scenes together capitalize on the humor they share. Sylvia Scarlett allowed the pair to be the character actors they are.

Both critically and commercially panned at the time, Sylvia Scarlett has gone through a massive reevaluation by critics and audiences. At the time, Hepburn's string of box office flops, like Sylvia Scarlett, hurt her career and could have prevented her from ever becoming the iconic star she was. While Hepburn didn't go on to play characters like Sylvia, she still gave a fantastic performance. She leans into the masculine traits that afforded her such strong and independent female roles throughout her career. Similarly, Grant isn't the suave leading man of his later years but a deceptive con man.

2 Holiday (1938)

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. Hepburn's Linda feels similarly, as even though she belongs to this wealthy family, she has never asserted her independence because of her father's influence. Johnny's appearance in her life is the catalyst for change.

The budding romance between Johnny and Linda is forbidden, as Johnny is engaged to Linda's sister, Julia, even though Julia has nothing in common with the free-spirited Johnny. Grant is at his best as a representation of the younger generation who wanted to change the world, coming into conflict with the traditional sensibilities of the older generation. This dichotomy exists in the films of every decade, and it's interesting to see the specifics of this dynamic played out in the late 1930s. The social commentary aside, it never gets old to see Grant and Hepburn fall in love.

Grant and Hepburn are sweet and charming throughout the film, capitalizing on their physical chemistry with comedic stunt work.

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. However, there's also an air of longing that they perfectly capture, as the love between Linda and Johnny is one they can't act on for most of the story.

1 The Philadelphia Story (1940)

Directed by George Cukor

For the last collaboration between Hepburn, Grant, and Cukor, the three creatives gave everything to the screen adaptation of The Philadelphia Story. Jimmy Stewart s them as another one of the many suitors clamoring for Tracy Lord's (Hepburn) affections. Based on the Broadway play of the same name, The Philadelphia Story also starred Hepburn on the stage, and there was no one else who could so perfectly capture the snobbery, beauty, and comedic timing of Tracy Lord. Grant plays her ex-husband, C.K. Dexter Haven, who hasn't gotten over Tracy and attends her remarriage to win her back.

The movie was so popular that the movie musical High Society was made in 1956 starring Grace Kelly, Bing Crosby, and Frank Sinatra. While the musical is enjoyable and features excellent songs, the movie remains the definitive version of the story, and a large part of this is thanks to Grant and Hepburn. In the early 1940s, divorce was still taboo, and The Philadelphia Story comments on the societal expectations of people with money and high social standing behaving with flawless moral integrity. Dexter behaves as he likes and isn't concerned with what people expect of him.

Conversely, Tracy tries to hide the imperfect parts of herself to maintain this illusion of control. However, it soon becomes clear that their characters need the other to balance them. After Hepburn starred in a series of movies with poor reception, The Philadelphia Story was her triumph and helped her turn the corner in her career. The film was a box office smash and saw Hepburn and Stewart both nominated for Academy Awards for their performances, with Stewart winning. Additionally, the script was just as important as Hepburn and Grant, as the actors shine with strong dialogue to deliver.