First time was as a sophomore at U.C. Santa Barbara, playing a party in front of our house on Del Playa Drive -- I had been playing guitar and piano for a few years before that, but bass maybe only six months or so. I would describe myself as an advanced beginner at the time.
We played a lot of covers (ten or fifteen) and a few originals. The covers -- CCR, Santana, Pink Floyd, Allman Bros., Eric Clapton. We had two guitarists, sax, a keyboardist (with a Hammond B3 and a leslie cab; owch, my back still hurts thinking about that thing), myself and drums. It went over fairly well, all told. Not our best moment, but not our worst, either.
The crazy part of this was that shortly thereafter -- within a few months -- we played a Friday night at the Whisky A Go Go, which actually went over very well. We were much tighter by that time.