Start with Junta, their first album. Very proggy and will give a laugh at times.  It is some of their most complex and best material. Every track is a highlight but "Union Federal", "Icculus", & "David Bowie" are my favs. Also considering you can sit through Unfold the Future you will appreciate that there is an hour of material on each disc, so buy it now!!! & dig in!!!!! A progger must have.

If you like junta check out their next 4 albums (RIFT).  While I haven't heard "A Live One" I have heard a lot of them live and that is where they REALLY shine (& make you laugh like on "Hampton comes alive" where they do Beastie boys "sabatage" & "gettin' jigy wit it") at least compared to latter albums, although "Round Room" & "Story of The Ghost are really good too!

Oh yeah, lets not forget that Trey Anastasio can play anything with almost always the same guitar sound.

Man Overboard wrote: Heard a few songs from various albums, much better than I was expecting...  any Phish fans know where a progger ought to start?

Personally, I feel their best work is scattered amongst several albums.  Songs like "Maze" from Rift, "Birds of a Feather" from Story of the Ghost, "Mike's Song" live from Slip, Stitch, & Pass, great live covers of "Bold as Love" and the late Son Seals' "Funky Bitch" too name a few.  So you're probably going to have to weed through some silly junk to get to the gems...but they are there.

BTW - Nine days ago you posted that you prefered Ronnie Stolt to Trey Anastasio (a perfectly reasonable opinion).  But now I'm wondering just how much Phish you had really heard before making that assesment...  Sorry MO, I just had to jab ya a little.  I would like to think maybe we inspired you to give Trey Anastasio and Phish a closer listen...and THAT is the kind of open-mindedness that makes this forum great!

I enjoy the live album that they released that has Quadrophenia in its entirety on it. I think they are superb live.

Dick Heath wrote: The Beatles White Album

I think Phish's covers are close to awful.  Don't get me wrong, I love Phish to death.  I've seen them live a ton and love it when they cover stuff, but it's more for the thrill of seeing them cover something classic than it actually sounding good.  After a listen or two it's time to shelve it.  They're best when they're hot and playing those great prog-ish songs from the first few albums:  Reba, Bowie, YEM, Foam, etc. 

The albums are good and all, but phish is all about the live scene.  If you want recommendations, just ask.  I've got a ton of 'em.

My favorite album is either Hoist (for a more electric sound) or Billy Breathes (for a mellower acoustic vibe).  These are, however, less "prog" and more "jam."  So if you're looking for the "proggiest" Phish album (a mistake in my opinion: they owe much more to the Grateful Dead than anybody ever labeled "prog") you should get either Junta or Rift, but if you're looking for the best Phish album period, get one of these two.

But really, the best way to introduce yourself to Phish is to go here (bt.etree.org) and use bitttorrent to get a free (and legal!) bootleg audience recording.