They were all fans of modern art and thought they were making an anti-war statement that their fans would accept. This was at the same time they finally felt comfortable about giving unguarded interviews to the press about their opinions on politics, culture, drugs and religion. Those last two really bit them in the ass.
(So well worth noting, in fact, that @mikecurtis back in post #12 and @Johanna in post #26 already noted it.) 
This one from 1954 is pretty trippy-looking:
Yeah, it would have blown the minds of the folks at Haight-Ashbury in 1966.
Hmmm, I associate the style of that artist (Jim Flora) more with mid-century “pop surrealism”, with traces of cubism, folk-art traditions, etc., than with 1960s psychedelia. It’s also not a million miles from the contemporary cartoons of Saul Steinberg, especially pieces like “Three Liberties”.
But I feel like all such works still have too much, I don’t know? angularity and negative space? to really give that groovy 1960s psychedelic vibe.
Pretty much all of the pre-1960s examples are various takes on Surrealism and Expressionism. Psychedelic art should be inspired by an altered state of consciousness. The first true Psychedelic visual art may well be as late as 1964 and Ken Kesey’s bus, Furthur. I suspect that was the template quickly picked up by musicians and the rest of the 1960s counterculture around 1965. It wasn’t long until all contemporary Surrealism and Expressionism was being labeled “Psychedelic” even if it wasn’t inspired altered mental states.
I’m sure it’s unintentional but man what was this artist smoking?
This depiction of the devil is weird and over the top even for people that are Christians.
released in 1959
And you wouldn’t believe it, despite of the cover and the title, it’s a great album!
Ira Louvin had addictions and was deeply troubled. It’s surprising he was able to perform music. Died in 1965. Wikipedia reports Ira helped design the Satan album cover.
Charlie Louvin had a better life and started a solo career in 1963. He lived until 2011.
I think I read that the photo was taken in a junkyard full of smoldering tires.
Satan was pasted in later.
The head looks kinda South Parky
I remember burning stumps with tires. We lost trees after a tornado. The tires easily fit over the stumps. Add dry brush and kerosene.
It was a intense, hot fire that burned at least 15 hours. It would be illegal to burn tires now.
I can imagine the pit where they took that photo.
You mean he’s not real?
How about the Mothers of Invention’s Freak Out? Zappa had no use for hippies, but this came out in June 1966. That would have been a year before the Summer of Love.