This is the movie with the longest name on our list, so we'll shorten it to 'To Wong Foo' for practical reasons. Released in 1995, this comedy has an all-star trio of men in the lead roles; namely Patrick Swayze, Wesley Snipes, and John Leguizamo. All three are playing against their usual roles as macho men; they're drag queens, embarking on a wild and wacky road trip which is all about a signed picture of Julie Newmar. As absurd premises for a movie go, that has to be somewhere toward the top.
There are a lot of fun cameos in this film, including Julie Newmar herself, as well as RuPaul and Stockard Channing. The road trip takes an unscheduled diversion when the three drag artists find themselves stuck in a backwater town, but while there they're forced to confront their own identities and insecurities.