Here's a couple real decent recent flicks I've really dug, and almost started a similar thread, but didn't, and also somehow didn't find this one.
They both coincidentally star Matthew McCaughna-however-you-spell-it, and are both worth at least 2 watches, in my opinion. I have, even though one was an unintentional re-rent, and I wasn't even mad when I realized it lol
The first one is from Guy Ritchie, called "The Gentlemen", and should be entertaining for our types especially...
The second is called "The Beach Bum", by Harmony Korine, the dude who made "Kids", and "Gummo", etc, back in the day... His character is now one of my inspirations, and I feel like I need to learn to write poetry lol
I could watch Up in Smoke every day and still laugh my ass off. The 80's are my wheelhouse so Breakfast Club, the Outsiders, 48 Hours, Trading Places. Stir Crazy killed me when I was a kid, loved that one too.