Moby Grape was formed in late 1966 in San Francisco and is known for being perhaps the best band to completely fail to succeed commercially (there were other, like scene originators The Charlatans (whose first album didn’t come out until 1969 when they had become irrelevant). As described by Jeff Tamarkin, "The Grape's saga is one of squandered potential, absurdly misguided decisions, bad luck, blunders and excruciating heartbreak, all set to the tune of some of the greatest rock and roll ever to emerge from San Francisco. Moby Grape could have had it all, but they ended up with nothing, and less." The “less” was a bad contract that their manager negotiated to own the name Moby Grape.
As songwriters, Moby Grape blended straight-ahead rock & roll, smart pop, blues, country, and folk accents into a flavorful brew that was all their own, with a clever melodic sense that reflected the lysergic energy surrounding them without drowning in it. Their first album was universally acclaimed but crushed by a marketing stunt: Columbia Records released five singles at once so DJ’s did not know what to promote and as such no song picked up enough momentum to make the Top 40. Personnel breakdowns, pot busts, bad managers and other calamities followed, but you won’t be disappointed listening to the first album (“Moby Grape”).
UPDATE: Having read the book, "What's Big and Purple and Lives in the Ocean?," I can report with more detail. Here's what went wrong.
Moby Grape's heralded first album was released on June 6th, just 4 days after the Beatles Sgt. Pepper - so much for airplay. The 5 simultaneously released singles were also drowned out by the avalanche of music surrounding the Summer of Love. Their record company, Columbia, flew all of LA rock and critic royalty up to San Francisco for a launch party at the Avalon that featured special purple orchids flown in from Hawaii, Moby Grape wine, and custom purple velvet boxes containing the five singles. This created the impression that the band was overhyped - the San Francisco equivalent of The Monkees.
Meanwhile, that night, three members of the band were returning to home in Marin County but instead decided to climb a hill and catch the breeze with some young ladies they had met and got busted for consorting with underage women. The next 18 months were laced with stress and efforts to avoid jailtime. The next week was the Monterey Pop Festival where many of the performers became huge stars by being part of D.A. Pennebaker's terrific documentary of the event. The Grape's manger, Mathew Katz, demaned a million dollars from the promoters to perform on film which resulted in them being moved from Saturday night just before Otis Redding, to Friday afternoon when the crowd was still filing in and of course they were not in the movie.
Concert dates outside of the SF Bay Area later that year were few and far between and took the band to obscure venues in smaller cities paired with the Mamas and the Papas and the Buckinghams. Katz never mounted any semblance of a proper tour. In 1968 they released a double album April 3, "Wow/Grape Jam" which reached #20 only because it had an extra low price for a double album.
Finally, during 1968 one of their founders, Skip Spence, got way too involved in destructive drug-addled behavior culminating in trying to break down the drummer's door with an axe and he ended up in The Tombs and later Bellevue Psychiatric Ward. The others contined on for a while but Katz, had arranged for the ownership of the name Moby Grape to belong to him and at one point created a completely different band - called Moby Grape - that toured the country, confusing and disappointing concert-goers and even the original band themsleves who discovered the ruse by seeing themsleves billed in a different city at the same time .