Kind of meh, really. No where close to what I thought it would be after hearing how iconic of a movie it's supposed to be. I'm sure I'm missing context because it came out in 1969 and there probably wasn't anything like it before, but it felt amateurish to me, almost like a 90 minute experimental you'd catch at a film festival.
To its credit, the movie is definitely unique. We don't know what's going to happen from scene to scene because the characters themselves don't know. That's sort of the point of the whole thing, just a couple of dudes riding their motorcycles across the country (maybe to New Orleans for Mardi Gras), open to whatever comes their way, born to be wild, all that stuff. And it works out great for a while… until it doesn't.
It's, I think, trying to be a parable and social commentary at the same time. I think people from both sides of the political spectrum can claim it as “theirs,” which is probably why Easy Rider has been regarded as a decent piece of art for 55 years now. Both Peter Fonda and Dennis Hopper did well in the roles as Wyatt (aka Captain America) and Billy, but the movie got twice as interesting once Jack Nicholson joined the pair. There's something about Jack that is magnetic every second he is on the screen.
I won't tell you how it all ends, though you probably know by now. For me, it wasn't anything super special, but maybe I've just seen so many good movies… and endings… that I can't enjoy some of the originators.