7. High Society
The musical remake of The Philadelphia Story. Considering it'd be hard to top the epic cast of the original, (Jimmy Stewart, Cary Grant, and Katherine Hepburn) High Society does it. This cast is equally as epic, starring some of the greatest voices, and faces, in music. Bing Crosby, Frank Sinatra, Louis Armstrong, and Grace Kelly. Bing and Sinatra are two of my heroes. I love old films, especially old musicals, and my film reality bar is usually set at black and white. (Which is why seeing something like Tranformers 3 is like opening an awesome black hole of over stimulation.) So when I get to watch Crosby and Sinatra
duet, or Crosby and Armstrong play "
Now You Has Jazz" it's like stopping time from awesomeness. This is one of those rare films where legends are working together. The set up is cute and simple. Crosby's C.K. Dexter Haven is still in love with his ex-wife Tracy Samantha Lord (Kelly) who is set to marry George Kittredge (John Lund). So
Spy magazine sends its two top reporters, Mike Connors (Sinatra) and Liz Imbrie (Celeste Holm) to get the low down on the wedding. Hillarity ensues when it's clear the Liz is in love with Mike who falls briefly for Samantha who's still clearly in love with Dexter who can't stand George and certainly shares Samantha's affections. It's a classic screwball rom-com before the term even existed. Because the film is so much fun it's impossible not to love it. The singing, the dancing, the acting, everything about it is like a time machine made of glory and champagne. It makes you wish you were as suave as Sinatra, as brilliant as Bing, and (for the ladies) as gorgeous as Grace. Grace Kelly is also the kind of dame you'd drop everything for, and if you'd been married and divorced from her like like Dexter, you'd happily take that plunge again because she's the gal you want to get it right with. The film has so much star quality that you sort of forget it's a simple love story and it becomes like watching a group of people you feel are your friends. That's tough to do, feel undeniably connected to a cast of characters you've never, and will never know. But that's what classic cinema does best, there's a certain level of charm that connects to it on a level you couldn't with any other film.