Easy Rider (1969)

  Well, at least nobody committed suicide this time.  Jesus this movie was depressing.  Not quite City of God depressing, but still.  And I will fully admit, I didn't get it.  I wasn't alive in the 60's (or 70's), so I have no contextual reference.  I've never been interested in the counterculture movement so I don't relate to the drug use.  Everything just seemed pointless and arbitrary.  Maybe Dennis Hopper (may he rest in peace) was going for that in a philosophical nihilistic sense, that life is meaningless except for the relationships formed with the people around you, but I'm just spitballing.

I will say the scene where Hopper, Fonda, and Nicholson are sitting around the fire smoking a joint and talking about UFOs reminds me of the horrible house parties I attended in high school.  Here's how much of a nerd/square I am:  I would get up and leave the room if someone lit up.  Not because I have a moral objection to marijuana.  I don't.  If you want to do it, knock yourself out.  I would leave because I thought it smelled disgusting and it gave me a headache.

Really, the only thing that kept me going were the cameos.  Phil Spector has no speaking part, but he's the dude in the Rolls buying coke from Dennis Hopper and Peter Fonda.  And Toni "Oh Mickey, you're so fine" Basil plays a prostitute named Mary.

And let's not forget that Jack Nicholson won an Academy Award for Best Supporting Actor for his role as the alcoholic lawyer.  He is easily the most accessible character.
Oh, and it has a seriously bitchin' soundtrack.