Thinkin' about this thread reminded me of the film "The Wackness." If you havn't seen it check it out. Everybody has seen the popular ones; Up In Smoke, Half Baked, Harold & Kumar, How High, etc. That one was a sleeper.
Music from the 90's, dope dealer who sells to a weed smoking suicidal psychiatrist played by Ben Kingsley of all people. Throw in Olivia Thirlby and you got a coming of age romance story. It's got more of an East Coast vibe to it. Cameos by Method Man and Mary-Kate Olsen.
Rep if you seen this. After, I'll give another recommendation.