86 Years Later, Rare Photos From 1940’s ‘The Philadelphia Story’ Capture the Trio Who Made Movie Magic

See behind-the-scenes photos of Katharine Hepburn, Cary Grant and Jimmy Stewart on set of the classic comedy!

By Abbey Bender January 13, 2026

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View gallery Cary Grant, Katharine Hepburn and Jimmy Stewart in a promotional photo for 'The Philadelphia Story'

Cary Grant, Katharine Hepburn and Jimmy Stewart in a promotional photo for 'The Philadelphia Story' Everett Collection

In ’30s and ’40s Hollywood, screwball comedy reigned supreme, and The Philadelphia Story, with its charismatic cast, witty dialogue and “comedy of remarriage” story structure, is one of the most iconic films of this genre. The film stars Katharine Hepburn as Tracy Lord, a Philadelphia socialite who is set to marry George Kittredge (John Howard) following her divorce from the memorably named C.K. Dexter Haven (Cary Grant). When reporter Mike Connor (James Stewart) comes to cover the high society wedding and Dexter reenters the picture, complications ensue, as Tracy finds herself at the center of a hilariously chaotic romantic situation and must choose which of the three men she wants to be with.

It’s no spoiler to say that The Philadelphia Story ends with Tracy and Dexter getting back together, and the road to remarriage is filled with laughter. Hepburn, Stewart and Grant make for one of classic Hollywood’s most delightful trios, and 86 years after the film debuted, it remains charming as ever. Read on to see rare photos that show how the cast and crew of the 1940 romantic comedy made movie magic.

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1. The director and his muse

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In this snapshot from the set, Katharine Hepburn smiles as the film’s director, George Cukor, runs through the script. Cukor, who blazed a trail as one of the few gay directors of the era, was a key figure in Hepburn’s storied career, as he directed her very first film, A Bill of Divorcement (1932). In addition to The Philadelphia Story, he also directed her in Little Women (1933), Sylvia Scarlett (1935), Holiday (1938), Keeper of the Flame (1943), Adam’s Rib (1949) and Pat and Mike (1952). They later reunited for the TV movies Love Among the Ruins (1975) and The Corn Is Green (1979), and their impressive creative collaboration endured for over 45 years.
2. She wears the trousers

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Here, Hepburn wears her signature trousers as she receives direction from Cukor. Hepburn sparkled in The Philadelphia Story, and with good reason—the film was an adaptation of a 1939 Broadway play in which she starred, and the role of Tracy was written specifically for her. Interestingly, the actress had been in a string of financially unsuccessful films prior to The Philadelphia Story, leading her to be branded as "box office poison," and the 1940 comedy marked her triumphant comeback and earned her an Oscar nomination
3. Poolside couture

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While she was known for her trailblazing embrace of menswear, Hepburn also looked lovely in a gown. Here, she wears a gorgeously draped number from the legendary Hollywood costume designer Adrian (who worked on well over 200 films, including The Wizard of Oz) as she stands with Cukor at the film’s elegantly appointed swimming pool set.
4. Smoke break

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Smoking was commonplace in Golden Age Hollywood, and here, Hepburn happily offers her gilded cigarette box to her costars, Jimmy Stewart (who won his only Oscar for his Philadelphia Story role) and Ruth Hussey (who played Stewart’s photojournalist colleague in the film) while Cukor looks on.
5. Diving board beauties

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Some of The Philadelphia Story’s most memorable scenes take place by the swimming pool, and here, Katharine Hepburn and Cary Grant look fabulous as they hang out at the diving board in between takes. Hepburn and Grant also starred together in Bringing Up Baby (1938) as well as George Cukor’s Sylvia Scarlett and Holiday, and their onscreen chemistry was the stuff that cinematic dreams are made of.
6. Giving pointers

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Here, Hepburn, Grant and their costar, John Howard, look serious as Cukor guides them through a scene. Looking back at the many times he worked with Hepburn, Cukor said, “With Kate Hepburn, I have to discuss all the minutiae: She's an extremely intelligent woman, full of horse sense, and she requires full explanations of every little thing she is doing before the camera.”
7. A casual interlude

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In this candid, a barefoot Hepburn takes a smoke break while flanked by Stewart (who looks quite spiffy in his suit and hat) and Cukor. Hepburn and Stewart were friendly both onscreen and off, and Hepburn said that the actor possessed “integrity that is most unusual.”
8. Just one of the guys

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Hepburn could always hold her own with the guys, and even once said, “In some ways I’ve lived my life as a man, made my own decisions. I’ve been as terrified as the next person, but you’ve got to keep a-going; you’ve got to dream.” Here, she reclines on the floor as Cukor and his crew gather around their equipment.
9. Rom-com on the radio

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The Philadelphia Story had a long afterlife. In 1956, it was adapted into High Society, a Technicolor musical starring Grace Kelly, Bing Crosby and Frank Sinatra, and the play was adapted for TV and radio broadcasts. Here, Hepburn, Grant and Stewart read their parts for a radio production of their film. At one point during their recording sessions, Grant and Stewart donned skirts in a playful homage to Hepburn’s penchant for wearing trousers.

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