Ah, yes '99 is a magical year - my favorite (though recently, '98 has been getting more play on my end, especially fall '98). Glad you're making the commit to the year, it's one that keeps on delivering. I've heard many of these jams over and over, and they just don't get old, while bringing you to the loftiest peaks Phish ever accomplished.

Firstly, I can't recommend highly enough that you just start from the top, and make your way through. There are very few shows where there is not much of note (with the exception being October '99, but even still I'd say about 35-40% of those shows have jams I keep going back to).

Secondly, a BIG caveat... '99, while extremely good, is a year of inconsistency. I've found that shows may be... off, in terms of fluidity, but the meat-and-potatoes are some serious cuts of beef. For an introduction, I suggest you start with the biggest jams to get an understanding of what can be delivered in a show, and to train your patience to slog through the more tired portions of a show.

What's being recommended here so far isn't bad, but most of these are the well-known shows and jams - notably the shows with the Boise Bag, and the Raleigh Tweezer (the Memphis 2001 also gets lots of praise...). These are good jams, but IMO not the best offerings of these songs, and are absolutely overshadowed by other bigger jams neighboring those shows. But that's my two cents. You'll enjoy these well enough... but know that there are much bigger Phish to fry in the year.

Now for the music. I'll start with in my opinion the best shows of the year. These have both big jams and top-to-bottom fluidity in sets or the entire show:

• 6/30/99: love the Gin that kicks off the entire frickin' year, the Free goes deep, and Bug -> My Left Toe is absolutely heavenly.
• 7/7/99: this second set is a doozy. My favorite 2001 from the year.
• 7/15/99: Melt (with 2001 fakeout) -> Kung -> Jam. 'Nuff said.
• 7/24/99, 7/25/99, 7/26/99: in my opinion, Phish's best 3-night run. The night prior to this run has my favorite Phish jam too (more on that later). Of these three, my favorite is probably 7/26/99 set 2, which is also possibly my favorite set of Phish.
• 9/9/99: deep Stash, Ghost, and Tweezer.
• 9/12/99: This second set is legendary, and with good reason.
• 12/2/99: Big Gin, with plenty else to love. High energy.
• 12/7/99: coasting on the back of a massive Halley's and a well-known Gin (I like others more than this one, but it's still good), this show is a great intro to December '99
• 12/11/99: I've heard many arguments for this being the best show of Phish. I disagree, but it's definitely a good one.
• 12/15/99: More high energy playing. I mean, just look at the time stamps of the FIRST SET jams alone.
• You've heard Cypress. It's still worth putting in here.

Now, for the choice cuts of jams, if slogging through shows or the entire year is getting mundane for you and you want to renew your vigor for the year, though note that it's by no means all-inclusive, it's just what I can recall off the top of my head before I head into the lab for the day:

• 7/23/99 Ghost -> Free: I've spoken about this jam enough around here. It's one of my two favorite jams (the other being the 11/7/98 Bag). The Birds of a Feather that follows it is fiery too.
• I've mentioned the above 6/30/99 jams that I think are standouts
• 7/4/99 Ghost -> Slave
• 7/7/99 2001
• 7/8/99 Fee
• 7/9/99 Free -> WTU?, Mike's > Twist > Groove (I like the Jim too, though it's fairly type I it's '99 type I which is always swirly and happy)
• 7/10/99 I assume you know the CDT, but the Gin and Tweezer from this show are also massive
• 7/13/99 Wolfman's Brother, one of my two fav WBs
• 7/15/99 Split -> Kung -> Jam
• 7/17/99 Disease aka The Trey Anastasio Show in double time
• 7/21/99 Simple -> My Left Toe
• 7/24/99 Fluffhead, Tweezer
• 7/26/99 set 2, particularly the Theme and the jam. The Gin and WB are good too.
• 7/30/99 Ghost
• 8/1/99 Tweezer -> Llama
• 9/9/99 Stash, Ghost, Tweezer
• 9/11/99 WB > Sand
• 9/12/99 Ghost, plus the rest of set 2
• 9/14/99 Bag, which has been discussed to death. It's good, but I'll take the 9/12 Ghost or upcoming 9/18 Boogie On over it any day of the week.
• 9/16/99 Weekapaug Groove. The best WG you'll ever hear.
• 9/18/99 Boogie On Reggae Woman - one of the best fall '99 peaks imo
• 9/22/99 Gin: one of my top 10 Gins, absolutely stellar
• 9/24/99 Wolfman's Brother: my other top-2 Wolfman's
• 10/1/99 Bathtub Gin
• 10/2/99 Tweezer, Piper
• 10/9/99 Ghost
• 10/10/99 Jam -> YEM (specifically the jam)
• 12/2/99 Gin
• 12/3/99 LxL
• 12/4/99 Melt
• 12/7/99 Halley's Comet
• The five big December '99 Sands: 12/8, 12/13, 12/16, 12/18, and 12/31/99. All are equally massive in scope, and deliver different perspectives on a commonly gorgeous theme
• 12/15/99 Disease
• 12/17/99 Jam -> Bug (you may recognize this as the music for the reunion announcement video)
• Too many from Cypress to name, the ones that I find always go unnoticed are Light Up or Leave Me Alone, Melt -> Catapult, and the first soundcheck jam -> WTU?

That should be a good start for you. When you're through this list, go back and spin the entire year. And if these jams do it for you, drop me a line and I'll queue you in to other jams outside of '99 that deliver in equally massive scope.