"Man Bites Dog" - quite controversial when it came out, actually was banned in 33 countries or thereabouts. Still legal in the U.S.
"Romeo is Bleeding" - always nice to see Gary Oldman go over the top
The uncut version of "True Romance" - Oldman over the top again, the legendary "dueling Brandos" scene with Dennis Hopper and Chrisopther Walken, and Val Kilmer as the hallucinated image of Elvis... Now that's a movie. Even Balkie from "Perfect Strangers" and a young Brad Pitt are along for the ride.
"The Way of the Gun" - a bleak picture, but you get to see the proper and slick use of the 1911.
"The Thing" from 1982, rapidly becoming a legendary "guy status" film. Have a bottle of J&B while you watch.
"Natural Born Killers" - "Be your dad Woody" was what Oliver Stone told Harrelson during the production. At the time Harrelson was best known as the doofus bartender on Cheers. His father was actually a contract killer, and may have shot JFK. The always strange Juliette Lewis was along for the ride and Tommy Lee Jones shows up as well.
"Love and a .45" - just an amusing little film
"Bottle Rocket" - got the Wilson brothers their start and got James Caan out of retirement.
"Surf Nazis Must Die" - once legendary for its strangeness, now just a foot note, but still a compellingly strange film.
"Caligula" - you'll never look at Malcolm McDowell the same way again.
"A Clockwork Orange" - just to complete your Malcolm McDowell experience.
The 1970s "Dillinger" with Warren Oats and Ben Johnson, where John Milius ("Red Dawn" et al) did his best to recreate the magic ambience of the "Wild Bunch".
And if you haven't seen it, "The Wild Bunch". William Holden's last great movie. "If they move, kill 'em".