Living between Boston and Burlington meant that I usually needed to travel for music, and though I had email in 1988, this was mostly Before Internet and that meant I didn't hear about Phish shows much.
During September of 1991 the Dead played six nights in Boston, and I saw a bunch of those, staying with friends for some, and commuting back and forth for others, keeping my day job. On one of the rides back home I met Donni, and in the course of the drive learned he was a big Phish fan. Told him what Marla had told me, and he said, "Gimme your number, I'll let you know."
So it came to pass that one day Donni called and said, "Phish at Dartmouth, next Sunday?" And I said, "Sure." I didn't know any of the music, hadn't heard any of it. I went in as a fan of concerts, knowing nothing of the band other than the raving recommendations of several friends.
I think it was Donni, Dave, and I who went together, and it was the first time I'd been to Webster Hall, which was tiny -- a seating capacity of only four hundred people. Open floor, U-shaped balcony with 5 rows of seats around the ring. Webster Hall is now the Rauner Special Collections Library. I think Phish was one of the last shows in the venue.
The show started, and halfway through the first song, The Sloth, I'm thinking, Uh, okay, WTF does this metal band have to do with Zappa or the Dead? I remember the lighting for Sloth being very black and white, emphasizing the metal character.
Then Paul and Silas: Everyone is bopping and I'm like, Ok, I actually like bluegrass, but what's up with the flow here? Where are we going? Maybe I need another smoke?
After Stash I looked at Donni and said, "Ok, THAT was good. More like that."
At the end of the first set -- killer Bowie -- my general reaction was, Excellent musicianship, some great songs, some ok songs, and some stupid filler weirdness that was distracting.
When the second set started I was still getting my bearings during Tube (because YOU MAY LEAVE AND RE-ENTER THE VENUE WITH YOUR TICKET STUB AND A HAND STAMP, WOOT!), but the Divided Sky had my undivided attention, and I remember thinking it was gutsy and rare for a band to trust the audience such that they could have so much quiet early in a second set.
Second set was better than the first, for this newbie. I knew "A Train" and liked their version and that they played it; loved the YEM. Golgi was a good closer. Then back to the Americana sorta-bluegrass for the encores.
Debriefing over a beer, decided that the Zappa influence was about the virtuosity and the hijinks, the Dead influence was about the jamming and flow within the songs. But really these guys are their own thing. Decided I needed to know the songs better to grok the flow between the songs -- because AFAICT it was random. "I could see them again," I said.
Little did I know how many shows I attend (though the Dead kept a lot of my budget for the early '90s) and how much I'd come to love the band's attitude, their approach to their craft, their infectious fun attitude, and their sophisticated non-trendy songs. In retrospect, a great first show.