Shrooms and Shenanigans: the night Woody Harrelson almost destroyed the Grateful Dead

When you think about the Grateful Dead and their live performances of epic proportion, you’ll often think about the crowds that used to frequent their performances and how dedicated they were to the cause of being Deadheads. An exhaustive knowledge of the band’s material and propensity for ingesting a lot of psychedelic and mind-altering substances are what immediately spring to mind when you think about fans of the Dead, and you can be guaranteed to find plenty of both of these at any one of their concerts.

While they might have been known for their stories of excess, there’s also a lot of adoration for the magic they made together as a group. So many of these devoted fans would probably have given anything for the opportunity to perform with them live or even be on stage at the same time as their favourite group.

Unfortunately, that’s a rite of passage reserved for only the most elite fans and probably not the sort of thing that the rest of the band would be willing to allow, considering how horrendously poorly it went the last time they invited one of their famous friends to accompany them on stage. Among one of the Dead’s most high-profile devotees is actor Woody Harrelson, and while he managed to befriend the group and charm his way into joining them on stage, his presence was something of a hindrance to the overall performance.

The Cheers star had got to know the group through his carpenter, who was already a friend of the band, and when he was invited along to go to a show with his friend, the two decided to ingest some psilocybin mushrooms before heading backstage to meet with the musicians. Evidently, this would have been enough excitement to handle, but considering how the drugs would’ve inhibited his judgement, he thought it would be a good idea to take the band up on the offer of being part of the performance.

His conversations with the band were quickly curtailed when they had to go onto the stage for their performance, but Harrelson was not willing to cease his discussions on the universe with Jerry Garcia or his chats with Bruce Hornsby about the Gulf War. When they took to the stage, he thought he would be able to sit down side-stage, but unbeknown to him, there was no chair to speak of.

What Harrelson unwittingly found himself sitting on was a live MIDI keyboard, which blurted out a number of dissonant notes over the sound system. The rest of the group looked around at Harrelson as if to suggest their disappointment in him, but the actor looks back on the moment with a small amount of pride.

“That was my first experience with them,” Harrelson later recalled on an episode of The Late Show with Stephen Colbert. “I jammed with the Dead.”

He might be able to loosely claim to have performed with his favourite band, but sadly for him, the musical career wasn’t his true calling. “If the acting thing hadn’t worked out,” Harrelson said when presenting the band with an award in 2025, “I truly believed I would have been an official member of the Grateful Dead. I’d settle for an honorary member, mascot, spirit animal, all of the above, if you’ll have me.”

Safe to say, they won’t be inviting him back as a keyboard player.

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