Podcast recommendation! Tucker Diedrich is a Wisconsin-based comedian. His friend Ross realized that Tucker has seen virtually none of the movies that anyone ever talks about, so they started a project wherein every week they watch a movie that Tucker should have seen, but didn't; and then they record a podcast episode where they talk about that movie.
I've listened to this podcast a while and have always enjoyed it, but I feel like they've really stepped up their game recently. Their taste in movies is different than mine, their analysis isn't particularly insightful (though occasionally Tucker will come up with a great question, like when he asks Ross about 2/3 of the way through their discussion of "The Rocky Horror Picture Show": 'Does anything happen in this movie?') But many of the episodes have unexpected moments that are hilarious in hard to describe ways, and I always find them to be entertaining, even if (or because) I disagree with their opinion of the movies.
You could start with the most recent episode, a discussion of 'Once Upon A Time In Mexico' that makes it sound like some kind of hallucinatory fever dream, or you could go back a half dozen episodes or so to 'Children of the Corn' or 'Rocky Horror Picture Show', which I think marks the beginning of a recent run of really good episodes; after that, you can go back and listen to the earlier ones if you get hooked.
I should note that all the episodes contain major spoilers, so you may only want to listen to ones that are about movies that you've never seen, or never plan to see. Or, like me, you may throw caution to the winds and listen to all of them.