How others will see it. High Society is famous for all the wrong reasons. That is, its remembered not for its quality, but as an apex of events. It marked the end of Grace Kelly, Hollywood A-List Actress, and the beginning of Princess Grace, benevolent ruler of Monaco. High Society was the pinnacle of Armstrong's film career, his momentum already stolen by the rock 'n' roll movement. The movie was the only screen pairing of old hand Bing Crosby and resurgent Frank Sinatra, two of the biggest selling American artists this side of Elvis Presley. "True Love," from High Society, was Crosby's last big pop hit, as well as the first (and last) for Grace Kelly. Crosby knows his career is on a downslope, but characteristically, he doesn't seem to care. He can afford to pay greens fees. Good for him.
How I felt about it. But what about High Society as a movie, rather than as a gathering of interesting actors, musicians, and future royalty? It's a dud. It's much more interesting as a cultural milestone than for the script and its overly familiar plot.
In the first scene, Louis Armstrong practically tells us what's going to happen. Bing Crosby, still gracefully mooning over lost hottie wife Kelly, wants to win her (and her spectacular body) back. We like Bing, even though he has played the same character in every film except The Country Girl. Cutie pre-teen Lydia Reed also likes Bing, a further confirmation of his inevitable re-conquest of Kelly.
We know that Kelly isn't going to marry George, because it's obvious (and increasingly so) that George is an uptight jerk who wants Grace not as a woman, but as the princess that Kelly would soon be in real life. We also know that wild card Frank Sinatra won't win Kelly either, because he's burdened with a sympathetic girlfriend, Celeste Holm.
Hence the only suspense comes in exactly how the engagement will break. This requires George to become even more of a prick than we thought was possible, while Kelly changes from a hypocritical and vindictive ice queen into drunken frat party jailbait. Was it because Daddy Dearest (a.k.a. Seth Lord, not to be confused with the evil emperor in Star Wars) told her to loosen up, or is it because Sinatra aimed his bedroom voice at her? Or was it because a film only lasts about two hours? I'm siding with the latter.