The Philadelphia Story delivered one of the most star-studded love triangles ever

My favorite exchange in The Philadelphia Story demonstrates the power of a comma. Upon learning that his fiancée isn’t entirely apologetic about the drunken flirtations she indulged in the night before their wedding, rigid George Kittredge (John Howard) and glamorous Tracy Lord (Katharine Hepburn) stumble into a couplet: “But a man expects his wife… to behave herself, naturally.” Tracy’s reformed ex-husband C.K. Dexter Haven (Cary Grant) turns those last words on their head, countering, “To behave herself naturally.” Though on the surface The Philadelphia Story is a story about class, its most poignant ideas center on the baggage we place onto women, the pedestals we put them on, and the pedestals they sometimes unintentionally climb onto themselves. The Philadelphia Story sees the notion of the flawlessly strong “woman who has it all” for the impossible standard that it is and instead champions space for human vulnerability—for women to behave, well, naturally.

In this case, the woman on the pedestal is Tracy, arguably the most iconic character of Hepburn’s six-decade career, and certainly the most important in terms of ensuring she had a career of that impressive length. Tracy is a Philadelphia Main Line socialite, and her upcoming wedding to a nouveau riche “man of the people” is the event of the season. But since she wants to keep the press out, Spy magazine reporter Macaulay “Mike” Connor (James Stewart) and his photographer girlfriend Liz Imbrie (Ruth Hussey) have to slip in incognito, using Dexter as their cover. Tracy almost immediately susses out what’s going on and forces Dex to reveal his true motives: Spy magazine is ready to print a story about her dad’s affair with a dancer and the only way they’ll hold it is if they can get an even bigger scoop about her wedding. Tracy reluctantly agrees, and soon sparks are flying as fast as the fake identity hijinks. The Philadelphia Story becomes not so much a love triangle as a love pentagon, with Tracy as the object of desire for Kittredge, Dex, and Mike, all while pragmatic Liz patiently waits for her boyfriend to realize he’s gone off the deep end.

Hepburn herself could be considered the auteur force behind The Philadelphia Story. After burning bright in the early 1930s, her career was on the rocks by the latter part of the decade. Following a series of commercial flops (including the now-renowned screwball comedy Bringing Up Baby), she was labeled “box office poison” by the Independent Theatre Owners Of America. Public perception turned against her too, the actress accused of being haughty and unlikable. So Hepburn bought out her RKO contract and set about shifting the course of her career with a tailor-made Broadway role.

Playwright Philip Barry wrote Tracy Lord with Hepburn in mind, using his friend and real-life Philadelphia socialite Helen Hope Montgomery Scott as his other influence. Hepburn financially backed the production and The Philadelphia Story was a smash-hit success on Broadway. More importantly, she accepted the film rights as a gift from then-beau Howard Hughes. She later quipped to biographer Charlotte Chandler, “I slept with Howard Hughes to get The Philadelphia Story. He was a brilliant man, and going to bed with him was very pleasurable. But the pleasure of owning The Philadelphia Story lasted longer.”

With every studio in town desperate to capitalize on the play’s success, Hepburn chose the one that gave her the most creative control. MGM agreed to let Hepburn star as well as bring on director George Cukor, who had directed her in her very first film and remained a close friend ever since. (They eventually made a total of 10 films together.) Clark Gable (as Dex) and Spencer Tracy (as Mike) were Hepburn’s first choices for co-stars, but they weren’t available at the time—probably for the best, considering that Gable had potentially contributed to Cukor getting fired from Gone With The Wind. Still, it was hard to complain about Cary Grant and Jimmy Stewart as replacements. Grant joined the project on the condition that he get top billing, then donated his entire $125,000 salary to the British War Relief Society.

If Bringing Up Baby sees Grant and Hepburn riffing on Shakespeare’s A Midsummer Night’s Dream, then The Philadelphia Story is their take on Much Ado About Nothing: a heftier but no less hilarious comedy of manners with a screwball edge. The character drama is buoyed by the comedy, and the comedy is given heft by the air of poignant melancholy that hangs underneath it all. Screenwriter Donald Ogden Stewart was charged with keeping the best bits of Barry’s play while streamlining its characters and expanding its world beyond the confines of the stage.

Everyone involved, but particularly Hepburn herself, had a keen sense that audiences wanted to see her taken down a peg. So the film opens with Grant literally pushing Hepburn flat on her back during the silent squabble that ends Tracy and Dex’s whirlwind marriage. Over the course of the next 112 minutes, Tracy is belittled, insulted, and embarrassed so many times it’s impossible not to empathize with her—and with Hepburn by extension.

Every man in Tracy’s orbit feels entitled to comment on exactly what they think of her, directly to her face. Her father (John Halliday) cruelly blames his infidelity on her lack of loving daughterly affection. Kittredge calls her a “marvelous, distant” queen in a way that feels like a threat; Mike calls her a “radiant, glorious” queen in a way the feels like the most romantic thing anyone has ever said. Only Dexter sees her icy demeanor for the act that it is. He comes the closest to accurately analyzing Tracy, which just makes his assessment ring harsher. She finds imperfection unforgivable, both in herself and in others. So she seeks out relationships where she’s worshipped as a goddess rather than loved as a true equal.

All that male entitlement can be frustrating to watch, especially because Barry’s script doesn’t deliver a ton of moral comeuppance. Tracy forgives the men who’ve cut her down, even though they haven’t particularly atoned for what they’ve said. Ultimately, however, that lack of didacticism is a virtue. The film’s plot eventually ties itself up in a neat bow, but the emotional undercurrent feels unresolved—a portrait of how things are rather than how they should be. Part of the experience of being an opinionated, outspoken woman is having the world constantly condemn you for it, all while you try to figure out which critiques are fair and which aren’t. Watching Tracy navigate that is bittersweet and honest, even if it doesn’t come with a big moral lesson at the end.

Notably, however, the women in The Philadelphia Story are much kinder to Tracy than the men are. Her mother Margaret (Mary Nash) largely shares Dex’s assessment, but doesn’t use it as a cudgel. Instead, she privately observes that “Tracy sets exceptionally high standards for herself, that’s all, and other people aren’t always quite apt to live up to them.” Tracy’s kid sister Dinah (Virginia Weidler, delightful) is an ally too, even when she disagrees with Tracy’s choice of a second husband. And the wonderfully magnanimous, endlessly practical Liz seems to have nothing but empathy for the situation Tracy is in—even when that situation involves turning her boyfriend’s head. Though she’s not billed alongside the three headlining stars, Ruth Hussey emerges as the secret heart of The Philadelphia Story, not to mention one of its biggest comedic scene-stealers.

Nearly eight decades later, there’s still an Avengers-like thrill in seeing Hepburn, Grant, and Stewart team up together in one film. Hepburn is, of course, absolutely flawless. Her voice seldom wavers and her impossibly statuesque physicality never slouches, but she always makes it clear that on some level Tracy’s carefree demeanor is an act, whether she fully realizes it or not. Hepburn is glamorous, appealing, and utterly heartbreaking all at once, particularly as she quietly admits, “I don’t want to be worshipped. I want to be loved.”

Grant has the trickiest acting challenge because Dexter has to emerge as the ultimate romantic hero while seemingly playing a passive role right up until the very end. It works because he projects a sense of intelligence and decency that implies Dex has spent his two years away from Philadelphia social life maturing into a better person (not to mention learning to manage his alcoholism). He comes back to help Tracy kickstart her own self-actualization journey, not expecting any reward for it, but still happy to get one in the end.

It’s also a treat to watch Stewart play against what was fast becoming his usual wholesome type. Snobbish, cynical Mike is about as far away from George Bailey as you can get, even if both characters wind up wandering in the moonlight with beautiful women. Stewart won his first and only competitive Oscar for the film—much to his own surprise, even after delivering arguably the best drunk acting ever captured on screen. (He’d voted for Henry Fonda in The Grapes Of Wrath and felt he won the award solely to make up for not winning for Mr. Smith Goes To Washington the previous year.)

Mike is sexy in a way not usually associated with Stewart. A flirtatious scene of Tracy and Mike undressing in adjacent poolside changing rooms highlights the creativity that emerged from the limitations of the Hays Code. And though their drunken affair may consist of nothing more than “two kisses and a late swim,” it’s as sexually charged as any romantic comedy scene has ever been. It also feels notable that the next morning, when asked why things didn’t go further between them, Mike explains, “You were a little the worse—or better—for wine, and there are rules about that.”

Later remade as the 1956 musical High Society starring Bing Crosby, Grace Kelly, and Frank Sinatra, The Philadelphia Story is what philosopher Stanley Cavell dubbed a “comedy of remarriage”—a subgenre of 1930s and ’40s films that got around the rigidity of the Hays Code by having characters divorce, flirt with other people, and then remarry, rather than carry out extramarital affairs. Even without a Production Code, however, romantic comedies of any era have to handle extramarital flirtations rather gently, if only to keep the romantic heroes likable. But Cavell’s larger point is that these films ultimately celebrate the idea of marriages of love and equality, in which two people agree to grow and mature together. Unlike in their impulsive, idealistic first marriage, Tracy and Dexter approach their second one with their eyes open, willing to accept that they’re both flawed human beings.

In comparison, the movie’s class commentary is fairly toothless, characterized by the way Mike’s disdain toward the rich melts into unadulterated love within less than 24 hours. At best, The Philadelphia Story offers a “let’s all come together!” sentiment to round off the Great Depression. At worst, it feels like a treatise on how the classes should just marry within themselves, thank you very much. In either case, Kittredge’s self-made millionaire doesn’t come across very well. On the whole, the class commentary is mostly just there to provide a comedic backdrop to what’s ultimately a character study, which is fair enough when it leads to hilarious scenes like Mike’s standoff with a suspicious butler or his encounter with an absurdly prim and proper librarian.

In addition to Jimmy Stewart’s acting win, Ogden Stewart won for Best Screenplay, and the film was nominated for four more Academy Awards, including one for Hepburn. Though she didn’t take home the trophy, she won her career back. The Philadelphia Story was a critical and commercial smash hit and exactly the game-changer Hepburn hoped it would be. The Time review opened with the line, “Come on back, Katie, all is forgiven.”

Which is fitting, given that The Philadelphia Story values empathy and forgiveness above all else. It isn’t interested in simplistically rosy happily-ever-afters. It ends with a final snapshot that messily freezes things mid-action. The film is often remembered for Mike’s quote, “The prettiest sight in this fine, pretty world is the privileged class enjoying its privileges.” But maybe a more fitting sentiment is the one Liz expresses in Tracy’s defense: “We all go haywire at times, and if we don’t, maybe we ought to.” The film is a rallying cry for embracing imperfections and tearing down pedestals. Ironically enough, that’s exactly what earned it a spot in the pantheon of all-time great romantic comedies.

Next time: Jennifer Garner is 30, flirty, and thriving in 13 Going On 30.