By 1938, Katharine Hepburn had been declared box office poison in the trades by theatre owners, who were pressuring studios not to use her in films. Her unconventional looks and her preference for playing strong women made her atypical of Hollywood starlets, and with a no-nonsense attitude refusal to play at celebrity (preferring to dress casually offscreen), she developed reputation of being mannish and arrogant. She left RKO and headed for New York, where Philip Barry wrote a play for her, basing the main character on her own personality. The Philadelphia Story ran for two years on Broadway.

She acquired the movie rights (thanks to buddy Howard Hughes), then turned around and sold them to MGM on the condition that she was the star and had the choice of director and co-stars. She'd take no salary, but 45% of the profits. George Cukor, who had directed her in 4 previous movies, was an easy decision. His work with women and matching stars' personalities with strong performances, was insurance that this movie would be a strong comeback for her, and it was a box office hit.

Two (of many) notable scenes:

  • Virginia Weidler launches into a spirited rendition of Lydia the Tattooed Lady;
  • An unscripted ad-lib caught on camera, when Cary Grant reacts to Jimmy Stewart's hiccup. If you look closely, you can see both actors start to break character and laugh, then contain themselves.
The movie won Oscars for best screenplay (to Donald Ogden Stewart), and Jimmy Stewart took home the Oscar for best actor (often thought to be a consolation prize for Mr. Smith Goes to Washington in 1939), Hepburn, nominated for best actress, lost out to Ginger Rogers. Also nominated were Cukor (Director), Ruth Hussey (Supporting Actress) and MGM (Best Picture).

The script was later remade into a Cole Porter musical, High Society, for Frank Sinatra, Bing Crosby, and Grace Kelly.