My most distinct memory of this show is the wind howling on the lawn and the fact that a bunch of people in my group took some fake MDMA that made them feel absolutely awful both during and after the show. Upon relisten, there's few notable musical high points.

Six of the eight songs in the first set were two years old or less at the time, which may help explain the truncated versions. The second-ever Phish version of First Tube feels rushed. What’s the Use is nice as a standalone instrumental, but that song is always more powerful when it emerges from a deep, dark jam. Will it Go Round in Circles was only played twice by Phish – one of those TAB songs that never quite found a comfortably place in the Phish canon.

Disease opens the second set in promising fashion, with Trey driving the band into a high-speed frenzy at about the 11 minute mark. The pace is sustained into the reprise, with this standalone 13+ minute version ending on an energetic note.
After a short Moma Dance, we get Piper that ends abruptly. Too abruptly.

Fee was rare enough to get people excited, and has a nice ambient extension in the outro, with Trey repeating the same notes over and over again (a style we’d see throughout Fall 99).
The debut of Jibboo is completely straightforward, but I Saw it Again is dark and creepy. Melt meanders much more softly and gently. Other than the long intro, the Bowie is pleasant but not memorable.

Disease and Saw it Again or worth a listen, but this show is mostly the band slowly finding their way into the fall 99 style of ambient jamming, for better or worse.

Fall 1999 gets a bit of a bad rep but when you actually go and listen to the shows, even the non-Jamcharted tunes have a lot to offer. I'm speaking specifically about the 40+ minute Melt>Cavern>Bowie combo that provides the meatiest jamming of this show, but gets no love from the Jamchart gods. This show is also rated far too low; the fact that there are only two reviews of 9-10-1999 on .net should give you an idea of this show's reputation...which to me, it doesn't deserve. This is a very underrated show.

The Twist, Divided Sky, WTU?, Disease, Fee>Jibboo, Saw It Again, the aforementioned Melt>Cavern>Bowie, even the Squirming Coil are all performed capably and they poot forth quite a bit of energy from their instruments on this night at the Gorge. There are much better shows from 1999 to be sure, but don't be put off by the relatively low rating, lack of Jamchart entries, or short song lengths; this show has the spacy vintage 1999 sound in spades and is worth a listen.