All Night Long (1962)
Patrick McGoohan and Charles Mingus walk into a bar...
I'll admit it. I watched this film because of the jazz and fact that it was released by Criterion. I kept watching because I was sucked into the plot of Shakespeare's Othello set in a 1962 London jazz club.
The film mixes actors and jazz musicians on the same stage. And it quite successfully sets the scene of a private jazz club on the Thames owned by ultra-wealthy Richard Attenborough in the role of Roderigo, or in the hipster parlance of the jazz scene, just "Rod." Dave Brubeck shows up and everyone stops and says, "Hey, it's Dave Brubeck!" exactly the way that they would have in 1962.
All Night Long is definitely worth your time. It contains some amazing performances from both actors and musicians. Whenever I watch an old film like this, I invariably end up on imdb and Wikipedia reading about the lives of the actors and directors. In this case, Betsy Blair, former wife of Gene Kelly and American ex-patriot who left America because of the Hollywood blacklist, was one of the more interesting paths of discovery.