
First of all, The Philadelphia Story—the non-musical version of this film—competes for my favorite movie of all time so my analysis of High Society is colored. The precedent for embodying the roles had already been set by a star-studded cast, complete with Katherine Hepburn, Cary Grant, and Jimmy Stewart. In High Society, Frank Sinatra played the role which had been Jimmy Stewart’s in The Philadelphia Story. Sinatra was a comfortable and witty character who was naive in his being oblivious to his love for the photographer and his quick plunge into love for the troubled yet beautiful socialite. This role reminds fans that Sinatra could balance his confidence and humor with his persona as the average guy who falls for a girl out of his league and is rejected. His confidence is highlighted especially when he sits down in the family room and witnesses the masquerade which the bride-to-be puts on and also whenever he relates to other people in the film. Sinatra lacks awkwardness. His confusion about his attraction towards Tracy Lord—played by Grace Kelly—seems to be one of his only moments when he doesn’t operate with as much social ease. That unstated confidence which Sinatra displays on the screen seems to match more closely the persona which he developed off-screen after his comeback.
Bing Crosby’s role in the film as the wise-cracking but loving singer who ultimately gets the girl reinforces his identity in relation to Sinatra. Bing Crosby was the original crooner and functioned as a sort of “godfather” in the industry when Sinatra was trying to emerge on the scene. His role in the film was much more dominant than Sinatra’s. Bing Crosby seemed more associated with a jazz singer role in the film, which made him more legitimate and more of an innovator. Sinatra’s function for singing was to croon and get the girl and also to play up the comedic portion of his role. When singing together, Bing seems older and more knowledgeable yet they both maintain a certain respect for each other. Bing tries to diffuse conflict whenever Sinatra and Kelly run into Kelly’s fiancé while scantily clad and very intoxicated. Even though Sinatra croons to Kelly in the bar and she nearly falls over and obviously struggles against her temptation, Crosby still ends up with her. The rivalry has changed by the time of the film and Sinatra has forged his own musical niche and identity that admitting defeat to Bing Crosby doesn’t create bad feelings. They are almost jokingly going through the motions of competing with each other.