Hmm, I just watched the movie of High Society, and I have to say that Grant/Hepburn/Stewart beats Crosby/Kelly/Sinatra. I really enjoyed it, I just think I would have enjoyed it more if I hadn't seen The Philadelphia Story first, because the songs meant that some of the awesome dialogue got compressed. Also, The Philadelphia Story is definitely sexier. Bing Crosby is bit too granddad for my tastes.

I also think I'd have enjoyed it more if I'd actually seen it on stage, because some of the film blocking was a bit meh. Although, how do they do the Louis Armstrong bits onstage?

TPS is definitely less fluffy, particularly Dexter's character. For 'composer of charming jazz' read 'alcoholic'.

So see both, enjoy both, and each to their own. The genius of Cole Porter cannot be denied.