A lot of people will say to start with the most well known stuff - Naked Lunch, On the Road. I never liked Naked Lunch much, but On the Road is still probably the best gestalt depiction of the post-war America that was smack in the middle of transitioning from post-depression NYC jazz to California hippie. Once you have a feel for what that time and context was, then the poetry makes more sense.

It's been a while, but I remember enjoying a lot the very early writings that were collected posthumously in Atop an Underwood, very easy to pick up arbitrarily. Other good ones - Desolation Angels, Dharma Bums, The Town and the City, Subterraneans, Satori in Paris. Those are all formative. There was another posthumous release And the Hippos Were Boiled in Their Tanks which was just a funny and ridiculous retelling of a murder of a friend.

Of course, lots of fun stuff from Bukowski, Gregory Corso, Gary Snyder, Phil Lamantia, John Clellon Holmes, Richard Brautigan, short stories and poems. Neal Cassady Collected Letters, 1944-1967 was probably my single favorite book back then. I'm sure I'm forgetting lots of stuff.

Oh and Dog https://www.youtube.com/watch?v=Hk8cMyCUnoo

Dharma Bums is my favorite Kerouac book, and I've read most of his. Bonus points if you have even a passing interest in Zen.

I can remember that one being my favorite too but I can't remember anything about it. It's been 35 years, probably time for a re-read.

I remember liking the subterraneans quite a bit.

Junkie by William S Burrough, while not of the beatnik genre is an excellent read.

It's set in the exact same time and place, and I think parallels the destructive nature of the Road in a more a direct way.

I think the Road is actually best read once as a teenager, once at midlife. The perspective change is enormous.