Romantic comedies are one of the oldest genres in movies.  They are often popular at the box office, but few stand out among the greatest films of all time.  The Philadelphia Story is an exception.  Not only was it instantly popular with moviegoers, it’s popularity has endured ever since. 

Tracy Lord (Katharine Hepburn) is a rich girl from one of the oldest families in Philadelphia.  She is about to marry George Kittredge, a man who has risen through the ranks of a company owned by her father.  As the wedding nears, her ex-husband C.K. Dexter Haven (Cary Grant) appears with reporter Macauley Conner (James Stewart) and a photographer Elizabeth Imbrie (Ruth Hussey) in tow.  The pair are from a Spy magazine, a paparazzi type publication that Tracy despises.  Under most circumstances, Tracy would never allow them anywhere near her wedding, but Dex reveals that the publisher of Spy magazine has a hit piece about her father ready to run unless the magazine is allowed to cover the wedding. 

We soon learn that things are a bit complicated with the Lord family.  Tracy seems excited about the wedding, but it does not take long for us to suspect that she is less than satisfied, as if she is doing what is expected of her or, more precisely, what she expects of herself.  Her fiancée George, who rose from a poor background, is pompous and protective of his prize.  Her ex-husband Dex, who comes from the same social class as Tracy, does not take himself or his background all that seriously and feels that his marriage ended because Tracy did.  The rest of the Lord family clearly adores Dex while tolerating George. 

When Mike Conner is thrown into the mix, things get even more complicated.  Tracy has never known anyone like him.  He is down to earth and unassuming.  He is honest and likeable.  A brilliant writer with a book to his credit, he works at Spy to pay the bills.  In her conversations with Mike, Tracy seems to be learning that there is another way to live.  Mike, on the other hand, soon forgets that he is there to report on the wedding.  They seem to be falling for each other, but we are never quite sure if it is the right match because Dex is clearly still in love with Tracy and photographer Liz is in love with Mike.  The one thing we are sure of is that George is not the right match. 

Despite having won an Oscar for Morning Glory (1933) and a second nomination for Alice Adams (1935), Katherine Hepburn’s career was on the decline in 1938.  It is hard to imagine that the screen legend was labelled “box office poison” after Bringing Up Baby (1938) flopped that year.  It is hard for this writer to imagine Bringing Up Baby flopping at the box office, but I will have to wait for another time to examine that.  In response, Hepburn bought out her contract with RKO Pictures and left Hollywood that year with hopes of resurrecting her career.  Her friend, playwright Philip Barry, had the perfect vehicle in play he had written with her in mind.  While initially skeptical, Hepburn agreed to play the role on Broadway in what turned into a very successful run.  Hepburn’s former boyfriend, Howard Hughes, bought the film rights to the play and gifted them to Hepburn.  With the means to control her own comeback, Hepburn sold the rights to MGM while keeping veto power over producer, director, screenwriter and cast. 

There are many reasons why The Philadelphia Story has endured and become one of few romantic comedies to also be considered one of the greatest films of all time.  The reasons can be boiled down to characters, cast and performances.  The three men in Tracy’s life reflect three sides of her that are in conflict.  George is the side that does exactly what her upbringing, wealth and status say she should do.  Mike is the side that wants to rebel and be just like anyone else.  Dex is the side that wants to take advantage of what she has been blessed with to chart her own course.   

These characters are expertly played by what seems the perfect cast.  Hepburn plays Tracy almost like she is portraying the same misunderstood person who was labelled box-office poison.  At first, we don’t really like her, but we sense there is more to her.  Stewart is the perfect actor to play the down-to-earth and endearing man who brings out a longing for normalcy in her.  Grant is also perfectly cast as the sophisticated gentleman who does not take himself too seriously and wants Tracy to see herself the same way.   

The supporting cast is also superb.  Ruth Hussey was nominated for Best Supporting Actress for her role as Liz.  Clearly in love with Mike, she sees something happening between him and Tracy but never seems all that worried.  Virginia Weidler, as Tracy’s precocious young sister Dinah, steals almost every scene she is in. 

The Philadelphia Story earned James Stewart his first and only Best Actor Oscar. Donald Ogden Stewart’s screenplay also won in the Best Writing, Screenplay category. The film was nominated in four other categories, including Best Picture, Best Director (George Cukor) and Best Supporting Actress (Ruth Hussey). Katherine Hepburn’s triumphant return to Hollywood earned her a third Best Actress nomination and the actress once labelled box-office poison went on to a total of twelve nominations and four wins – both records.