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How others will see it. Classic film fans should eat this up. After all, it stars two legendary actors, Grant and Hepburn, has an affecting supporting role by Lew Ayres, and charming supporting roles by like-minded Edward Everett Horton and Jean Dixon. The happy ending is easily guessed midway through the film, and machinations to get there are a bit contrived. The characters have unaccountable discrepancies. We'll get into all this shortly. The truth is, though, most classic film lovers won't care a whit about any of my objections.
Many viewers won't watch it, though, simply because it is a "creaky" "dated" black and white movie. If they happen to stick with it out of curiousity, they might develop a nagging suspicion that it is better than Shrek 3, not that they'll consciously admit it.
How I felt about it. Holiday is a good movie. I recently viewed The Philadelphia Story, a much better known and more acclaimed film that is reminiscent of Holiday. Both films star Grant and Hepburn, and are directed by George Cukor with a screenplay by Donald Ogden Stewart. And, both use the tried-and-true plot device of a pending marriage that a third party secrety wants to spoil, for all the right reasons. One of the would-be newlyweds, you see, has it all wrong, and is thus not right for the other (and assuredly not good enough.)
I like Holiday better than The Philadelphia Story, probably because it generates warmth during its more intimate scenes. The Philadelphia Story is instead an exercise in frustration, watching a potential home run batter sending pitch after pitch into foul territory. Holiday, at least, has pleasant early moments, before Daddy Oldbucks enters stage left and lets us know the tide has turned against the movie.
Once that happens, we learn that our affable Mr. Grant has been leading a (nearly) full time double life as a rising securities dealmaker, the equivalent of a nighttime vaudeville comedian spending his days as a brain surgeon. We also learn that the unheralded Doris Nolan, who has seemed so nice all this time, actually has an aloof mindset like her captain of industry father. Her newfound hardened nature opens the door for Kate Hepburn to take over the movie and get her man, something we suspected (to an increasing decree) would happen all along. After all, she's top billed.