High Society and Second Chances: The Philadelphia Story

Released in 1940 and directed by George Cukor, The Philadelphia Story is a quintessential romantic comedy starring Katharine Hepburn, Cary Grant, and James Stewart. The narrative centers on Tracy Lord (Hepburn), a proud, strong-willed Philadelphia socialite preparing to marry a wealthy but remarkably dull self-made man, George Kittredge. Her upscale wedding plans are suddenly upended by the simultaneous arrival of her charismatic ex-husband, C.K. Dexter Haven (Grant), and a cynical tabloid reporter, Macaulay “Mike” Connor (Stewart), who has been blackmailed into covering the high-society event alongside photographer Liz Imbrie.

As the wedding festivities commence, tension builds between Tracy and the three very different men vying for her affection. Her rigid, high-minded exterior begins to crack under the dry wit of her ex-husband and the unexpected poetic charm of the middle-class reporter. A night of heavy drinking and a late-night swim with Mike lead to a series of classic misunderstandings, forcing Tracy to confront her own vulnerabilities, her harsh judgments of others, and what it truly means to be a compassionate human being rather than an untouchable goddess.

On the morning of the wedding, the romantic chaos reaches its peak. Will Tracy go ahead with her marriage to George, or are Mike and Dexter a better fit for Tracy?

 

Ruth Hussey, James Stewart, Cary Grant, and Katharine Hepburn

George Cukor (1899–1983) was one of Golden Age Hollywood’s most sophisticated and enduring directors, celebrated for his elegant visual style, literary adaptations, and extraordinary skill at guiding actors to career-defining performances. Often labeled a woman's director due to his brilliant collaborations with fierce leading ladies like Katharine Hepburn—with whom he made ten films, including Little Women and The Philadelphia Story—Cukor possessed a sharp comic wit and a deep empathy that transcended gender, making him equally adept at handling sharp screwball comedies, lavish musicals, and intense dramas. Over a career spanning more than fifty years, he earned five Academy Award nominations for Best Director, finally winning the Oscar for the 1964 musical masterpiece My Fair Lady, and cementing his legacy as a master craftsman of classical American cinema.

Born Archibald Leach(1904 – 1986) in England, Cary Grant overcame a deeply traumatic childhood to become the definitive archetype of the debonair, sophisticated Hollywood leading man. Known for his impeccable comic timing, mid-Atlantic accent, and effortless physical grace, he moved seamlessly between screwball comedies like Bringing Up Baby and intense suspense thrillers directed by Alfred Hitchcock, including North by Northwest and Notorious. Grant remained one of Hollywood’s biggest box office draws for over three decades, famously retiring from acting in 1966 to focus on raising his daughter.

Katharine Hepburn (1907 – 2003) was a trailblazer whose fiercely independent spirit, sharp intellect, and unconventional style redefined femininity on and off the silver screen for over sixty years. Her career was a masterclass in resilience; she repeatedly defied studio executives, wore trousers when it was considered scandalous, and successfully revived her career whenever the industry tried to write her off. With a record-breaking four Academy Awards for Best Actress across six decades for films like Morning Glory, Guess Who's Coming to Dinner, The Lion in Winter, and On Golden Pond, Hepburn stands as one of the greatest legends in cinematic history.

Beloved for his distinctive drawl and slow, deliberate delivery, James Stewart (1908 – 1997) embodied the quintessential decent, honorable, and relatable everyday American man. His early career thrived on idealistic, vulnerable roles in Frank Capra classics like Mr. Smith Goes to Washington and It's a Wonderful Life, but he later displayed remarkable dramatic depth in darker Westerns and complex Hitchcock psychological thrillers like Vertigo and Rear Window. A decorated World War II bomber pilot who rose to the rank of Brigadier General in the Air Force Reserve, Stewart’s enduring integrity made him one of the most respected and cherished figures in American culture.

 

The Philadelphia Story trivia

• Before making the film, Katharine Hepburn had been labeled box-office poison by theater owners after a string of commercial flops, prompting her to return to Broadway to star in the stage version of this story. She wisely purchased the film rights to the play with the financial help of Howard Hughes, allowing her to control her Hollywood comeback by handpicking the studio, director, and co-stars.
• James Stewart won his only competitive Academy Award for Best Actor for his role as Mike Connor, a victory that surprised him because he felt Henry Fonda deserved the award that year for The Grapes of Wrath. Stewart famously sent the Oscar statuette back home to his father in Pennsylvania, who proudly displayed it in the window of his hardware store for many years.
• The famous scene where Mike Connor visits Dexter Haven’s house while heavily intoxicated features a completely improvised moment when James Stewart lets out a sudden, genuine hiccup. Cary Grant, caught off guard but staying perfectly in character, ad-libbed the response, asking him to clear his throat, which George Cukor loved so much he kept the unscripted interaction in the final cut of the movie.
• Katharine Hepburn originally wanted Clark Gable to play the charming ex-husband Dexter and Spencer Tracy to play the reporter Mike, but prior film commitments kept them from signing on. Cary Grant was then brought in, demanding top billing and a massive salary of $137,000, which he entirely donated to the British War Relief Fund.

 

Click HERE to watch the movie on The Internet Archive.

Click HERE to join the online discussion on July 13, 2026, 6:30 p.m. Central Time. Once you RSVP, you will receive an invitation with a link to join the discussion on Zoom.

 

Publicity photo with Hepburn, Grant, Steward, and John Howard

Discussion questions

1. How does Tracy Lord’s character arc challenge the concept of the idealized, flawless woman, and what does the film say about the danger of putting a romantic partner on a pedestal?
2. In what ways does the movie use the contrast between the wealthy Main Line elites and the working-class journalists to critique or defend the American class system of the era?
3. Do you believe Tracy made the right choice by returning to Dexter in the end, or did she have more genuine growth and compatibility with Mike?
4. How does George Cukor’s directing style and the snappy, fast-paced dialogue of the screenplay shape the balance between broad comedy and deeply personal drama?