Classic Movie Duos: Katharine Hepburn and Cary Grant

Katharine Hepburn and Cary Grant only made four movies together, but each one is worth watching for the formidable duo and the ways in which they are markedly different from one another. Two of their collaborations, Bringing Up Baby (1938) and The Philadelphia Story (1940), are highly regarded and much beloved, but their other two pictures, Sylvia Scarlett (1935) and Holiday (1938), are less celebrated, and, in fact, three of their four movies together were originally box office duds. With only four films to get through, it's a worthwhile project to sit and down and watch all of these movies as a group in order to appreciate the ways in which the stars work together and the career trajectories that they were charting when these pictures were being made.

Hepburn and Grant in Sylvia Scarlett (1935)

Hepburn and Grant first worked together on the most obscure of the four films, the gender-bending dramedy, Sylvia Scarlett (1935), in which Hepburn takes the title role and Grant plays the English conman who becomes her mentor and travel companion. George Cukor, who directed all but one of the pair's collaborations, is at the helm here, too. This is the only one of the four movies in which Hepburn and Grant do not play romantic partners, and in retrospect it seems odd that they don't get together here, especially since Sylvia's partner of choice, an egotistical painter played by Brian Aherne, seems just as problematic a mate as Grant's slippery but ultimately compassionate con artist. For Grant the movie was a step along the way to stardom, but for Hepburn it came during a troublesome slump that saw her cast in one flop after another. It's not a perfect movie, but Hepburn's cross-dressing provides a delightful opportunity for the star to show off her athleticism and escape the glamorous trap of a typical leading lady role. 

Bringing Up Baby (1938)

The second outing, Bringing Up Baby (1938), switches to Howard Hawks for direction, but that change did not save the screwball comedy from a bad box office showing on its release. Hawks thought that the movie flopped because all of its characters are crazy, but it has since soared to the status of a beloved masterpiece of its genre. The wacky story of a free spirit socialite (Hepburn) who wrecks the measured life of a paleontologist (Grant) casts our two stars in very different roles from their previous collaboration, and each gives a fantastic performance. Hepburn makes the leap to full-blown comedy and is simply hilarious, while Grant embodies a meeker personality driven to distraction by the outrageous obstacles he faces. While the movie didn't immediately pull Hepburn's career out of its slump, it has become a favorite film for her fans, and it set the two stars up for more romantic pairings in their next two films.

Holiday (1938)

Holiday (1938) came out shortly after Bringing Up Baby but found the two stars and director George Cukor at Columbia instead of RKO, which had made the two previous films. Once again the movie failed to gain traction with audiences, although the critical response was more positive. Adapted from a hit play by Philip Barry, the story once again put Hepburn and Grant into a mix of comedy and drama but this time set them up as characters who are obviously destined to get together, never mind that Grant's upwardly mobile protagonist, Johnny Case, opens the movie as the intended groom of the wrong sister. Hepburn once again plays a free spirit socialite, but this time family pressure has kept her penned in and unhappy until Grant arrives as a breath of fresh air in the oppressively lavish mansion. Edward Everett Horton and Jean Dixon also liven up the place as Johnny's friends, and Grant gets to show off a little of his acrobatic skill with Hepburn very game as his partner. While it's not as hellbent for hilarity as Bringing Up Baby, Holiday deserves attention for its compelling performances and its artful casting of the two leads, who are each just right for the parts they play.

The Philadelphia Story (1940)

Hepburn fans already know that the last of the duo's collaborations, The Philadelphia Story (1940), proved to be her big comeback. The romantic comedy from MGM picked up six Oscar nominations, including nods for Hepburn, Cukor, and supporting actress Ruth Hussey, with Jimmy Stewart winning for Best Actor and Donald Ogden Stewart taking home the award for Best Screenplay. Like Holiday, this movie was adapted from a play by Philip Barry, but in this case the original role had been written specifically for Hepburn, who also owned the film rights thanks to Howard Hughes. The story opens as if it might be a sequel to Holiday, with Hepburn and Grant's romance gone sour and the lovers now divorced, but Grant's character, C.K. Dexter Haven, isn't willing to give up his ex-wife to a new groom without a fight. Tracy Lord is another of Hepburn's socialite roles, beautiful and smart but rather spoiled, although Tracy is not about to be bossed around by anyone, especially her wayward father. 

Although only the final film proved to be a box office success, each of the Hepburn-Grant collaborations contributed to that last production in different ways, whether by building the relationships between the stars and their director, refining the character types the stars played, or establishing that Philip Barry's work was a good fit for the pair. Hepburn would make one more film adapted from a Barry play, Without Love (1945), which was also originally written for her, but in that picture her costar would be her longtime companion and collaborator, Spencer Tracy. While Hepburn and Grant would each make many more films, their work together ended on a high note with The Philadelphia Story.