Withnail and I (1986)
Loved this, so many good lines and nice subtle humor. I enjoyed all the main performances and loved the script. Definitely not a movie for everyone, but if you enjoy British humor then you really owe it to yourself to give this one a viewing if you haven't already.
Earlier Richard Linklater film that is very much like his later work, specifically the movie
Waking Life (2001). More of a look at Gen X in the early '90's with no real connectivity or plot. Definitely a film to watch if you're a movie buff or enjoy Linklater's work, but definitely not for everyone.