Walker 1987 is probably the last actual left wing movie that got made by a major studio in Hollywood. It basically ended the directors career.

It's about early colonisation in Central America and starts off as a traditional American pro colonisation movie and then descends into madness, the timeline randomly breaking with anachronistic objects like coke bottles and cans (central Americas new coloniser - see Coke anti union death squads in Colombia), or cars and helicopters. The credits roll real footage of Americans committing war crimes. I wont lie, it's kind of a slog at points, but still quite cool. Soundtrack by Joe Strummer of The Clash too.

Otherwise, for another wacky one - Accidental Death Of An Anarchist - originally by playwright Dario Fo about Italian fascists, it got adapted for British TV with seemingly zero supervision. The result is sort of a very blatant left wing monty python. You might have to stick with it a little bit - I think the first 10 minutes aren't as strong as the rest of it. The best part: https://youtu.be/kllonwGMTfw It's free on YouTube.