https://en.wikipedia.org/wiki/Trey_Anastasio" rel="nofollow - Trey Anastasio (most well known as guitarist and lead vocalist of Phish) is a very eclectic solo artist. He's produced a variety of content over the years and delivered a multitude of different genres to the forefronts of his albums. He's done neo-classical progressive rock, jazz rock, experimental rock, the whole shebang. His bands include  http://www.progarchives.com/artist.asp?id=1483" rel="nofollow - Phish , http://www.jazzmusicarchives.com/artist/surrender-to-the-air/" rel="nofollow - Surrender to the Air , Phil Lesh & Friends,  and his very own https://en.wikipedia.org/wiki/Backing_musicians_for_Trey_Anastasio" rel="nofollow - Trey Anastasio Band (originally known as Eight Foot Fluorescent Tubes). Many of these different bands have eclectic, progressive juices (Phish is on this website of course), and this transpires into all of his work. I believe that all of these progressive tangents he's done, he has made a few significant progressive rock albums over the years under his solo name. 

Below is Anastasio's discography and links to the most progressive songs on the albums. If you wish to peruse the rest, the link to the full album / playlist of the album will be there. Any incomplete playlists there that are unfinished are created by me and consist of all of the available YouTube tracks from said album. The albums are only those released under "Trey Anastasio" and "Trey Anastasio Band". 

-One Man's Trash (1998)- (mostly unavailable on YouTube, here's some https://www.youtube.com/playlist?list=PLLDfqwHSy5FKtKIMz3c9fx9tUu-eQ63gQ" rel="nofollow - tracks , and some http://www.allmusic.com/album/one-mans-trash-mw0000970926" rel="nofollow - samples )

1. Happy Coffee Song (2:39)

2. Quantegy  (2:59)

3. Mister Completely (2:41)

4.  A Good Stalk (0:50)

5. The Dream Machine (1:30)

6. The Way I Feel (2:55)

7. Rofa Beton (2:40)

8. For Lew (My Bodyguard) (1:39)

9. At The Barbecue (2:01)

10. Tree Spine (0:50)

11. Here's Mud In Your Eye (1:11)

12. The Real Taste of Licorice (2:33)

13. And Your Little Dog Too (4:00)

14. Jump Rope (fast version) (0:36)

15. Jump Rope (slow version) (2:19)

16. Kidney Bean (0:33)

1. Alive Again (4:39)

2. Cayman Review (4:16)

3. Push On 'Til the Day (7:37)

4. Night Speaks to a Woman (4:01)

5. Flock of Words (4:32)

https://www.youtube.com/watch?v=_HP19OISg4M" rel="nofollow - 6. Money, Love and Change (4:07)

7. Drifting (3:42)

8. At the Gazebo (3:11)

9. Mister Completely (4:35)

10. Ray Dawn Balloon (3:29)

https://www.youtube.com/watch?v=gMdyyRRnDQg" rel="nofollow - 11. Last Tube (11:22)

https://www.youtube.com/watch?v=Rw7xkd3rMIA" rel="nofollow - 12. Either Sunday (3:40)

- https://www.youtube.com/playlist?list=PL7EBxC3X_FJTArAZTRv2mbsDArkv6DyKE" rel="nofollow - Seis De Mayo (2004) - (with lineup of Anastasio and 66-piece orchestra)

https://www.youtube.com/watch?v=9jMTMU8V350" rel="nofollow - 1. Andre the Giant (3:42)

2. Prolouge (Pebbles and Marbles) (2:40)

3. The Inlaw Josie Wales (3:47)

4. All Things Reconsidered (3:01)

https://www.youtube.com/watch?v=B6ifuZKeLp0" rel="nofollow - 5. Coming To (2:50) 

6. Discern (intro) (1:50)

7. Guyute (11:46)

- https://www.youtube.com/playlist?list=PL7EBxC3X_FJTWp_CsCkZnuDSW6F69XzpS" rel="nofollow - Bar 17 (2006) -

1. Host Across the Potomac (6:05)

https://www.youtube.com/watch?v=QGd75-SgM0M" rel="nofollow - 2. If You're Walking (5:47)

3. Dragonfly (3:52)

https://www.youtube.com/watch?v=5q9-RJokT14" rel="nofollow - 4. Bar 17 (8:52) **

5. Mud City (4:04)

6. Let Me Lie (3:15)

https://www.youtube.com/watch?v=F2wXakOLsb8" rel="nofollow - 7. What's Done (5:43)

https://www.youtube.com/watch?v=sEo7jXYYGtc" rel="nofollow - 8. Goodbye Head (7:05) **

9. A Case of Ice and Snow (4:42)

10. Empty House (3:57)

11. Gloomy Sky (5:56)

https://www.youtube.com/watch?v=8VyOzVaeMXU" rel="nofollow - 12. Shadow (5:26)

https://www.youtube.com/watch?v=A5bM6hy8HdY" rel="nofollow - 13. Cincinnati (6:31) **

- https://www.youtube.com/playlist?list=PL7EBxC3X_FJTX2zdrP8pP0OyzBvzCCwlP" rel="nofollow - The Horseshoe Curve (2007) - (this one is one with the most jazz-rock on it)

https://www.youtube.com/watch?v=qZc7z8SLa-Y" rel="nofollow - 1. Sidewalks of San Francisco (4:06)

2. https://www.youtube.com/watch?v=TnwSlVC946g" rel="nofollow - Olivia (8:22)

https://www.youtube.com/watch?v=87Ft1zYJXmE" rel="nofollow - 3. Burlap Sack & Pumps (6:58)

4. The 5th Round (6:19)

5. The Horseshoe Curve (6:20)

https://www.youtube.com/watch?v=Rkg9Yvieo5M" rel="nofollow - 6. Noodle Rave (5:14)

https://www.youtube.com/watch?v=Z_om1i59xp0" rel="nofollow - 7. Tube Top Tony (3:34)

https://www.youtube.com/watch?v=F2yUakQXpQg" rel="nofollow - 8. Porters Pyramids (2:53)

- https://youtu.be/j4BxvqpbpSs" rel="nofollow - Time Turns Elastic (2009) - (this is the real stand-out and possibly the most progressive release Anastasio's done. I can't find the original studio recording on YouTube, but there are several live performances with the New York Philharmonic, linked in-title)

1. Time Turns Elastic (29:38)**

-a. Song at Dawn (5:23)

-b. Ruby Shaded Sea (4:02)

-c. Submarine (3:33)

-d. Landslide (8:35)

-e. Rays of Blue Light (7:23)

-f. Silver Sound Shower (2:03)

-g. Hailstorm (2:39)

-h. Funnels (7:01)
-i. Carousel (2:28)

2. Time Turns Elastic (Original Acoustic Demo) (13:29)

- https://www.youtube.com/playlist?list=PLduNMAHGtVNSfv6Fn0tOLtZIiQITECxuZ" rel="nofollow - TAB at the Tab (2010) as Trey Anastasio Band - (this one is a live album but features very progressive renditions of other songs)

https://www.youtube.com/watch?v=KGSXlFcfVVE" rel="nofollow - 1. Money, Love & Change (10:35)

2. Words to Wanda (5:02)

https://www.youtube.com/watch?v=2Ly_MaUc97A" rel="nofollow - 3. Alaska (8:21)

4. Valentine (7:05)

https://www.youtube.com/watch?v=gpzyr2WwY00" rel="nofollow - 5. Sand (12:01) **

https://www.youtube.com/watch?v=kTlUqJbhOoo" rel="nofollow - 6. Windora Bug (8:27) **

7. Drifting (7:33)

https://www.youtube.com/watch?v=XIZHUt8IJAE" rel="nofollow - 8. Goodbye Head (6:54) **

9. Show of Life (5:27)

https://www.youtube.com/watch?v=Zkv4WX9EYBY" rel="nofollow - 10. Black Dog (6:07)

https://www.youtube.com/playlist?list=PL7EBxC3X_FJTMX42-B5Tm9fEUlcH-u9_0" rel="nofollow - -Traveler (2012)-

1. Corona (3:35)

2. Let Me Lie (3:23)

3. Frost (3:57)

https://www.youtube.com/watch?v=HF5K6x55-Uo" rel="nofollow - 4. Land of Nod (3:32)

5. Pigtail (3:55)

https://www.youtube.com/watch?v=2oJUkVKeFJw&index=6" rel="nofollow - 6. Scabbard (6:02)

7. Clint Eastwood (3:45)

https://www.youtube.com/watch?v=KL-KZhhDbcQ" rel="nofollow - 8. Architect (4:05)

9. Valentine (6:14)

10. Traveler (6:37)

11. Greyhound Rising (4:41)

- https://www.youtube.com/playlist?list=PL7EBxC3X_FJRZi-umFJOBZwzY8i-0A5Sm" rel="nofollow - Paper Wheels (2015) - (really not that prog of an album at all, so no recommends here)

1. Sometime After Sunset (5:42)

2. The Song (3:26)

3. Never (6:01)

4. In Rounds (5:47)

5. Flying Machines (4:07)

6. Invisible Knife (4:39)

7. Lever Boy (4:17)

8. Bounce (5:52)

9. Liquid Time (6:18)

10. Paper Wheels (4:47)

11. Speak to Me (4:33)

12. Cartwheels (4:02)

So this is pretty much it. I just spent two hours making a overly-long post that'll just get rejected. Thought I'd bring some of it to PA's attention just for a bit of checking out. Cheers. 

EDIT: I forgot Anastasio's 2005 album https://en.wikipedia.org/wiki/Shine_%28Trey_Anastasio_album%29" rel="nofollow - Shine . It's not really that progressive of an album but the playlist is https://www.youtube.com/playlist?list=PL7EBxC3X_FJRcuwp3epTcfOZdxjdXfrr6" rel="nofollow - here .

Other links:

http://trey.com/" rel="nofollow - http://trey.com/

https://en.wikipedia.org/wiki/Trey_Anastasio" rel="nofollow - https://en.wikipedia.org/wiki/Trey_Anastasio

To get an artist accepted into Prog Related these days he or she firstly has to be a well-known name who has influenced prog on a wider scale in some tangible way or other, and you will then need to find a Special Collaborator to make a case for them on your behalf and present it before our admins, who might then take it to the private area off the forum where they discuss such matters, but Prog Related is a bit of a contentious issue around these parts just lately, and some high-ranking members of the site are in favour of scrapping the category altogether as far as new additions are concerned.

If Trey Anastasio is to be included on the site at all, it would have to be in one of our 'proper' subs, and suggesting him would almost certainly open up the Phish debate all over again.