There are a lot of different kinds of psychedelic record. At least a thought experiment or historical gauge, I would differentiate between music that is explicitly psychedelic, involving actual ingestion by the musicians or overt expression of them, and music that is just psychedelia, more of a style or an approach, which I think manifests both as a certain kind of whimsy with an emphasis on wordplay, like Sgt. Pepper's or Smile, but also in a sense of free form open-endedness, either through improvisation or tape collage or other technique that somehow breaks out of the standard-time of pop.
"The first LP of the Grateful Dead's ‘Live/Dead’ surely acted as a star map for many more heads' spaces over the years, giving it an edge in the popular vote."
In that the musicians were tripping constantly while writing and recording the material, and the music is a pretty self-conscious and successful articulation of psychedelic thinking, I’d make the argument for the 13th Floor Elevators’‘Easter Everywhere’, very much the product of LSD philosopher Tommy Hall. But as an album, the first LP of the Grateful Dead's ‘Live/Dead’ surely acted as a star map for many more heads' spaces over the years, giving it an edge in the popular vote.
It's hard to be sure if the Dead were actually tripping that night. Some probably were, surely many in the crowd at the Fillmore West were, too. But the Dead's writing and approach to improvisation – and especially that suite of music – really came from a long term engagement with LSD. Both the lyrics and the modal improvisation in ‘Dark Star’ very consciously evoked the flow and feelings of a psychedelic trip, with really detailed interplay between Jerry Garcia and Phil Lesh, especially, becoming especially vivid with eyes closed. The lack of tangible structure in the jam was (and is) a perfect place to let the mind wander, and get some thinking done, whether on psychedelics or not.
Jesse Jarnow (@bourgwick) is the author of Heads: A Biography of Psychedelic America and Big Day Coming: Yo La Tengo and the Rise of Indie Rock . He maintains @HeadsNews and a regular Heads News email bulletin. Since 2008, he has hosted The Frow Show on WFMU, the long-running freeform New Jersey radio station. He lives in Brooklyn.