The Night The Grateful Dead Channeled Beat Generation Icon Neal Cassady

On Valentine’s Day 1968, the Grateful Dead took the stage at the Carousel Ballroom in San Francisco, their first performance since their show on February 4, 1968, the same night Neal Cassady tragically died at age 41. The band’s members were close to Cassady – an unforgettable force of human and artistic expression who was a prominent Beat Generation figure – and they dedicated the second set of the concert held 56 years ago to their beloved friend.

Cassady served as the inspiration for the character Dean Moriarty in the 1957 book, On The Road, which fellow Beat icon Jack Kerouac wrote. On The Road told the epic tale of Kerouac’s character Sal Paradise’s cross-country journey through America that captures the essence of the era. The book and its author had an important impact on Grateful Dead guitarist Jerry Garcia, who often spoke of his affection for the book he read as a teen shortly after its release.

“Kerouac became so much a part of me that it’s hard to measure,” Garcia reportedly said. “I can’t separate who I am now from what I got from Kerouac. I don’t know if I would ever have had the courage or the vision to do something outside with my life, or even suspected the possibilities existed, if it weren’t for Kerouac opening those doors.”

In the mid-1960s, Cassady encountered author Ken Kesey, who wrote another influential novel, One Flew Over The Cuckoo’s Nest. Kesey and Cassady were central components of the counter-cultural collective known as The Merry Pranksters who were responsible for the psychedelic-enhanced Acid Tests featuring performances by the Grateful Dead. Cassady, who was a notoriously adventurous driver, was behind the wheel of The Merry Pranksters’ kaleidoscopic bus known as Furthur for the 1964 trek from San Francisco to New York.

“It is this time-frame’s version of the archetypal American adventure,” Garcia said in a 1993 interview when asked to compare Deadheads touring with the Grateful Dead to On The Road. “It used to be that you could run away and join the circus, say, or ride the freight trains. One of the things that was fun about the early hippie scene was, all of a sudden all those people were around and you could meet them. I mean, Neal Cassady, meeting him was tremendously thrilling. He was a huge influence on me in ways I can’t really describe.”

Grateful Dead guitarist Bob Weir was also influenced by Cassady. Weir namechecked “Cowboy Neal the wheel” in his song “The Other One,” which was played on February 14, 1968. Weir described Cassady’s relationship with the Grateful Dead while being interviewed alongside Garcia for Interview Magazine in 1991.

“From what I can see, our family situation is more or less modeled after old style big families, like you would find in Mexico or in Spain or in Europe or something like that, where you have a paterfamilias,” Weir explained. “In our case, I would say the paterfamilias would probably be Neal Cassady. He’s gone now. There was this myth, this icon that’s come up that Jerry here is. But it doesn’t really work like that. Our group dynamics are we’re brothers, we’re all siblings, we’re all underlings to this guy, Neal Cassady. You know, if anything, he was a father figure to me and for the rest of us.”

Cassady’s death deeply affected Grateful Dead bassist Phil Lesh, who like his bandmates, held Cassady in high regard. Lesh shared memories of his emotional state when the band took the stage for the first time following the death of his friend. In his memoir, Searching For the Sound, Lesh recalled his experience on February 14, 1968, writing:

“We opened the Carousel on St. Valentine’s Day 1968, an event that was clouded for us by the loss, 10 days earlier, of Neal Cassady. Neal, apparently in response to a wager about the number of railroad ties on the track between Nogales and San Miguel, had died of exposure while walking the tracks and counting. It hardly seemed credible that a life force like his, so generously endowed with the rhythm of motion through time, could be smothered and shut down at such an early age (he was [41]).

“When I told a friend we’d lit a candle for Neal, his response was, ‘Did you light it at both ends?’ My reply: ‘No, in the middle; it gives off more light that way.’ That’s how Neal lived: giving off more light than heat, ceaselessly interacting with the multitudinous cast of characters (including everyone he’d ever met and some he hadn’t) living inside his head, infinite waves of probability dancing around him like a cloud of cherubs — ‘Over here, Neal!’ ‘Me!’ ‘No, me!’ — or snuggling up to him as if they were warm puppies.

“On opening night at the Carousel, we dedicated the second set to Neal’s memory and played the full sequence of new music we’d been working on. That performance led us to settle on the particular sequence of songs that would appear on the album [Anthem Of The Sun]. I truly believe we were channeling Neal that night.

“The music was such a living thing: growing and changing from bar to bar, with his turn-on-a-dime responsiveness to context and novelty. More than once I thought I saw, out of the corner of my eye, a nine-pound sledgehammer describing a graceful arc through my field of vision. When we listened back to the show, it was spectacular — vivid, protean, and relentless.”

Garcia led the dedication to Cassady before the start of the second set of the band’s show which also featured Country Joe & The Fish. Posters for the Valentine’s Day ‘68 concert, designed by acclaimed artist Stanley Mouse, read “Be Mine” alongside an image of cupid.

After the dedication to Cassady, the Dead started the second set with the potent “That’s It For The Other One” suite, beginning with Garcia singing the heavy “You know he had to die” lyrics. Weir then shouted out “Cowboy Neal” within an emotionally charged “The Other One.”

The Cassady-inspired set continued with “New Potato Caboose,” “Born Cross-Eyed,” and one of the early appearances of the “Spanish Jam.” The subsequent “Alligator” saw Weir invoke tongue-in-cheek alternate lyrics referencing other local venues by singing, “Burn down The Fillmore, gas the Avalon” and Garcia quoted Donovan’s “There Is A Mountain” (well before The Allman Brothers Band made it the basis for “Mountain Jam”).

The set ended with a free-spirited “Caution (Do Not Step On Tracks)” bleeding into a extensive “Feedback” segment. The encore was keyboardist Ron “Pigpen” McKernan leading a cover of the R&B classic “In The Midnight Hour.”

Listen to the full Grateful Dead concert from Valentine’s Day 1968 featuring the second set dedicated to Neal Cassady, released as Road Trips Volume 2 Number 2, below:

Setlist (via JerryBase.com)

Set One: Morning Dew, Good Morning Little Schoolgirl, Dark Star > China Cat Sunflower > The Eleven > Turn On Your Lovelight

Set Two: Cryptical Envelopment > The Other One > Cryptical Envelopment > New Potato Caboose > Born Cross-Eyed > Spanish Jam, Alligator > Drums > Alligator > Caution (Do Not Stop On Tracks) > Feedback

Encore: In The Midnight Hour