I'm somewhat sad nobody has mentioned Mystery Science Theater 3000. They have a few classic episodes available to watch, but the new season that was brought back through Kickstarter is labeled as The Return. Some of the best comedy out there, IMO. If you're not familiar, the main part of the show revolves around a guy and his two robot friends riffing just terrible, terrible movies. Give it a chance, trust me.

Also, with the passing of Tom Petty, I can't recommend Running Down A Dream enough. It's a 4 hour documentary about his life and it is superb. One of the best I have ever seen.