This is completely off the top of my head, and to me these shows were my top 3 even though I attended others that were considered "epic":
1. 12.7.98 Worcester Centrum: The next night was the 1st show picked for the Live Trax series I think (night 2 in Worcester), and it was a stunning show (I'll never forget that Last Stop closer), but I was 4th row for this show and had brought a DMB fan buddy without telling her how good our seats were going to be. It was 1st Charlie Brown "Christmas Time Is Here" and then they took forever tuning for the final encore which was "Halloween" which they didn't play much then and my jaw hit the ground and I actually could see Dave & Stefan laugh at my expression of total shock. Tim R & Bela onstage, and just so much about this show that was stunning & memorable.
2. 2.24.95 Roseland Ballroom: This was one of the 1st DMB shows I saw and it was incredible. Apparently the Watchtower from this is one of the all time highly rated ones (Trey A and John Popper on it, I listened again the other day and it iS epic), also they played past midnight and 2.25 is my birthday so... It all felt like quite the birthday present! After this show everyone went to a tiny venue called Fez to see TR3 which Dave announced to the whole audience at Roseland, and the whole band did actually go to the show. It was a memorable show, memorable night.
3. TIE: 7.31.98 Meadows Music Center & 9.3.95 Jones Beach: Even though I'd go on to see shows up until 2004, I just remember having the BEST TIME at these early shows when almost every song sent me into a trance or launched me into orbit. Danced my ass off (well did that for most shows through 2004) but REALLY just got lost in those performances.
All these shows also had other non-performance amazing aspects to them that make them stand out, but the shows alone were transformative.
For Dave & Tim shows:
1. 2.11.96 Amherst
2. 2.17.96 U Connecticut
3. 1.24.97 Syracuse
For all of them I just remember alternating the entire shows between blissful singing, jaw-dropped open at the incredible versions, laughing until I cried at the stories, and sometimes something totally unexpected, like Dave and Tim doing "Interpretive Dance" to a Soul Coughing song... They were just amazing shows.
And the last one Syracuse, I had a friend working at the theater who let me in before soundcheck, I was allowed ot walk around the theater but when Dave & Tim started soundchecking I sat on the floor behind the last seats, couldn't see them, just listened, and to hear them play off of each other and practice new things and talk quietly (but into mics) was priceless. And yes security knew I was sitting there!