A proposed double-bill: Slava Tsukerman's Liquid Sky (starring Anne Carlisle) and Kathryn Bigelow's The Loveless (starring Willem Defoe), both from 1982. Liquid Sky, to me, is the cooler movie, in that I respond more to its sci-fi signifiers than The Loveless' rockabilly aesthetic, but both are essentially movies looking at subcultures, eroticizing them, and using fairly spare dialogue. Both are really cool, highly recommended, pretty weird, etc. I feel the only real piece of insight I have is noting their similarities to each other. The Loveless looks backward in time while Liquid Sky, while not set in the future, is a science fiction piece set in the time in which it was made. While The Loveless was probably shot somewhere in the south, Bigelow would've recently left Columbia University, in New York, and the fifties bikers look like punks in a lot of ways: Notably, the presence of swastikas tattooed on hands makes me view its nostalgia through that lens. Liquid Sky is made by Russians, but the cast is New Yorkers- Carlisle's other most notable role seems to be a small part in Desperately Seeking Susan.
Another NYC-oriented double-bill would be to watch A Thousand Clowns, directed by Fred Coe and starring Jason Robards, and follow it up with Little Murders, directed by Alan Arkin. Two movies about struggling with male adulthood, both adapted from plays (by Herb Gardner and Jules Feiffer, respectively), both of which are pretty exhausting to watch. All the dialogue absent from the previously suggested double-feature is present here, and while it's all pretty funny, either movie by itself is a bit much to take in one sitting. Both of these movies are really relatable, and while A Thousand Clowns sort of has hope, Little Murders is a bleak point of view to contend with.
While the first set of movies proposed are all about style and subculture, the characters in the second set of movies are alienated from society to such a degree that subculture would not be a respite. Great stuff all around.