The plots are very similar, so I’ll just try to go with the common points of the story. Tracy Lord (Katharine Hepburn, PS or Grace Kelly, HS) is getting married again. Her ex-husband, C.K. Dexter Haven (Cary Grant, PS or Bing Crosby, HS) is back in town, hoping to get her to come back to him. Tracy also has to contend with a writer, Mike Connor (James Stewart, PS or Frank Sinatra, HS) and a photographer, Liz Imbrie (Ruth Hussey, PS or Celeste Holm, HS), who are there from SPY magazine to cover her wedding. Tracy feels pressure from her father and Dexter, who are trying to remind her that nobody is infallible, including her, which increasingly confuses her, and leads her to start drinking too much champagne, almost getting her into an affair with Mike Connor.
Not really much to say here on the similarities, since High Society is a remake, and does make use of a good fraction of dialogue from The Philadelphia Story, so we’ll just dig into the differences. Obviously, one big difference is the fact that PS is a comedy/drama, whereas HS is a musical. The setting also changes, with it being Philadelphia in PS, whereas it is in Newport, Rhode Island (which may have been because the film was planned as a combination of two films projects, one was a remake of PS, and the other was planned on the Newport Jazz Festival).
The actors’ portrayals are also different. With Cary Grant, I’m left with the feeling that he is bitter over the divorce, which is why his words feel like they have a little more venom, while Bing Crosby’s Dexter is not quite so bitter, and almost seems to have come to terms with the idea of her remarrying (although he obviously wishes it could be him). With Katharine Hepburn, I can’t help but feel like her Tracy Lord has always been a bit of a snob, looking down on other’s faults, while Grace Kelly’s Tracy seems like she wasn’t always so bad (as shown through her flashback when she is reminded of Dexter’s ship the “True Love”), mainly changing as the result of when her father cheated on her mother. And as to the two reporters from SPY magazine, James Stewart and Ruth Hussey’s characters seem more like they wish they could do what they want, but their necessity for money dictates that they have to work for SPY, while Frank Sinatra and Celeste Holm’s characters are doing this as a normal job.
As to my own opinion as to which movie I consider the better movie? That would be High Society. I do enjoy both movies very much, but I usually prefer musicals and I like Bing Crosby as an actor. My opinion of The Philadelphia Story has definitely improved (and being able to see it restored on Blu-ray helps a little), but that opening scene still bothers me. I understand how it was done partly for audiences of the time who didn’t like Katharine Hepburn and wanted to see her knocked down, but it still bothers me, since I still don’t have that frame of mind. If not for that scene, I do think it would be a lot closer for me, but I still prefer High Society. However, both movies are wonderful, and I would certainly recommend watching either of them and making up your own mind!
The Philadelphia Story (1940)
My Rating: 9/10
High Society (1956)
My Rating: 10/10
The Winner (in my opinion): High Society