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I only saw Strangelove recently (much to my chagrin and great shame), but this one is really, really tough. Both from the 60s, both indisputably classics. They both run on elements of drama and comedy, although the latter is darker, deeper, and (at the same time) sillier in Strangelove. Sundance has more fully developed characters, more warmth, and a stronger human bond, less satirical as it is. It's difficult, but I don't think Strangelove - for all its many strengths - is enough to topple Sundance.
Sundance is more of a popcorn movie, brainless adventure escapism. Strangelove had a darker message but laughs at our impending doom at the same time.
BUTCH AND SUNDANCE is a great film, one I have seen many times, but you have to get up pretty early in the morning to beat Stanley Kubrick when he sets out to conquer a genre. I would vote DR. STRANGELOVE the funniest movie ever made.
I respect Dr. Strangelove. It has a lot of things going for it. Peter Sellers' performance(s) was all that left any sort of indelible impression upon me, though. And I never enjoyed Dr. Strangelove quite as much as Butch Cassidy and the Sundance Kid. It might be fluff by comparison, but I'll be darned if it's not superb fluff.
I LOVE both of these, but Strangelove is one of the most perfectly made comedies of all time.
Butch and Cass get my vote.