Some Like It Hot (1959), produced and directed by Billy Wilder.
After witnessing a gangland massacre, two musicians hide out in a girl band. It's a classic: nonstop quips and sexy situations. In the second half Marilyn Monroe is the nakedest-looking dressed woman I have ever seen.
I think you have to be in a certain mood for this one. It's the Monty Python formula for comedy: put on dresses and shriek a lot. How much you like it depends on your opinion of: how funny is Jack Lemmon? How roguishly charming is Tony Curtis? How comically alluring is hard-drinking Marilyn Monroe? None of these points have unanimous agreement.
I'd forgotten the big ugly gangsters, including Mike Mazurki, last seen in Night and the City (1950).
The Blu-ray is a big upgrade over my old non-anamorphic DVD and is available for rent from ClassicFlix. Netflix doesn't have it.