Today, Katharine Hepburn is celebrated as a trailblazing icon of Hollywood’s golden era—a fashion rebel with an androgynous (and possibly queer) style whose record four Best Actress Oscars remain unmatched. But in 1938, just six years into her illustrious career, she was famously labeled “box office poison.”
Ahead of her time, Hepburn’s commanding screen presence struck audiences as abrasive and haughty by the late 1930s. After the commercial failures of Bringing Up Baby and Holiday—now considered rom-com classics—she left Hollywood and starred in The Philadelphia Story, a play written by her friend Philip Barry.
Like its later film adaptation, Barry’s script follows Tracy Lord, a high-society snob (widely seen as a stand-in for Hepburn) preparing to marry a wealthy politician—until her ex-husband, C.K. Dexter Haven, and a tabloid reporter, Mike Connor, disrupt the wedding.
The play was a Broadway smash, and Hepburn quickly took control of the film version, bringing in director George Cukor (A Star Is Born, My Fair Lady). Her first choices for co-stars—Clark Gable and Spencer Tracy—were rejected, but the final pairing of Cary Grant and James Stewart as Dexter and Mike proved magical.
Hepburn and Grant, in their fourth and final collaboration, perfected one of rom-com’s greatest duos. Hepburn’s sharp-talking, strong-willed heroines often overpowered lesser male leads, but Grant matched her with effortless charm. As sparring exes, they needle each other’s flaws—Dexter’s drinking, Tracy’s icy facade—yet share undeniable chemistry.
But it’s Stewart’s Mike who delivers the film’s most swoon-worthy moments (and sets a high bar for drunk acting). The night before the wedding, his poolside flirtation with Tracy builds into a breathtaking confession of love, fueled by Stewart’s raw sincerity. “You’re lit from within, Tracy. You’ve got fires banked down in you, hearth fires and holocausts,” he pleads. Cukor’s dreamy direction captures them in moonlit close-ups, Hepburn’s eyes and beaded gown shimmering—every inch the goddess Stewart sees.
Yet the film doesn’t let her stay untouchable. The Philadelphia Story thrives on Tracy’s humbling—she must shed her arrogance to find love among mere mortals, satisfying audiences eager to see Hepburn knocked down a notch. Some, like Kazuo Ishiguro, have criticized the film as “a really nasty piece of work,” especially given how screwball comedies often focus on deflating male egos.
But the script deserves praise for its depth: each character in the love triangle is flawed, hiding behind defenses. Tracy’s happy ending is entirely her choice—she only surrenders to love when she finds someone who truly sees her.
Among screwball heroines, Tracy Lord stands out as one of the most layered. She’s spoiled, arrogant, and emotionally guarded—yet undeniably captivating. Under Hepburn’s command, you can’t help but fall in love.Under Hepburn’s spell, you’ll be utterly charmed.
The Philadelphia Story is streaming on HBO Max in Australia and available to rent in the UK and US. For more Australian streaming suggestions, click here.
