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The Story of the Ghost cover is a painting by George Condo, a decade before he did Kanye's MBDTF cover.
Round Room (bottom row, 2nd from right) is an image of the "Barn Ball" by New York sculptor and conceptual artist Lars Fisk (who is pictured inside it), BA UVM, MFA Columbia, and represented by Marlborough, who from the mid-'90s acted as creative director for the band's music festivals and some other special arena performances before becoming studio and facilities manager at Socrates Sculpture Park for the better part of the last decade (he's no longer involved).
Rift (top line, right) is the creation of New York artist David Welker, an early fan who worked with the band to create a piece for the conceptual album that embeds references to all of the its songs save one, "The Horse"...
...Hence the cover art for the follow-up, "Hoist" (second row, left), which the band passed on titling "Hung like a" etc. The horse in question belonged to the band's "first fan," who several years earlier had hosted their eighth anniversary and arguable first big end-of-summer gig, a forerunner to their much bigger festivals, at her farm near Portland, ME.
Junta (top line, left) is the creation of the keyboard player's college roommate Jim Pollock, who now mostly engages in printmaking in his noted-children's-book-author wife's native Chicagoland, and whose work, like that of many artists associated with the band, is much sought after by crazy Phish fans who will line up out the door for occasional gallery exhibitions of his poster art etc.
A Picture of Nectar (top line, second from right) is a picture of Nectar Rorris, owner of still-extant Nectar's bar in Burlington, VT, the band's Cavern Club cognate (the song from which the album title is derived is entitled Cavern), superimposed upon an orange for reasons I don't remember and may not exist
I have no idea who did the Lawn Boy (top line, 2nd from left) cover, and note only the turf-embedded appearance of the vacuum cleaner that the drummer had begun occasionally "playing" in the year prior.
Farmhouse (bottom row, 2nd from left) is an image of a carving on the door to an outhouse adjacent to the 200-year-old Burlington-area barn that Trey Anastasio restored and turned into the studio and living space in which the band recorded the album. "The Barn" continues in use by the band and sometimes other acts, though it has been turned over for much of the past decade to city-funded arts education and short-term visual-artist-in-residence programs. The outhouse itself is not 200 years old, but was created as a prop for a film made by the bass player and starring the late Col. Bruce Hampton of the Hampton Grease Band, et al, who had earlier appeared in Sling Blade and an episode of Space Ghost.
Crimes of the Mind (middle row, 2nd from left) is not a Phish album per se, but rather a Phish-backed effort by a slightly nutty college/prep school friend (now a public school teacher in the Bronx) that either label and/or band likely released to move contract satisfaction along, as may be true of the live double that followed (middle row, next over). I know nothing about the cover art (and am not sure I've ever heard the album).
The Billy Breathes cover is a fisheye photo of the bass player's already-enormous nose, selected on the spur of the moment late in the recording process. I have no idea if it's a King Crimson reference, but at least some of the band are big Crimson fans, and it wouldn't be the only cover to be referential in that fashion. For instance...
Undermind (bottom row, right), the band's last album before they broke up (and then un-broke up and released several more albums not picture above), is an image of the four band members arranged in what may be taken as a nod to a certain other well-known band's last album before they broke up
― Moo Vaughn, Sunday, 18 March 2018 18:14 (six years ago) link
Here are some of those not pictured or mentioned yet...
Slip Stitch and Pass, a live album that Christgau has deemed their best, whose cover was designed by the late Storm Thorgerson of Hipgnosis who designed dozens of album covers and more for Pink Floyd (DSOTM among many others), Led Zeppelin, Genesis, ELO, UFO, Wings, and many others
http://phish.com/wp-content/uploads/2010/03/SlipStitchPass.jpg
Joy, the reunion album, was designed by New York "psychedelic" artist Fred Tomaselli, represented by James Cohan in the US and White Cube in the UK, and whose work has also been included on Magnetic Fields, Eleventh Dream Day and Laura Cantrell album covers, as well as in The Wilco Book
https://upload.wikimedia.org/wikipedia/en/7/74/Joyphish.jpg
Fuego, the follow-up, was designed by partly SVA-trained and LA-gallery-repped contemporary Spanish surrealist Paco Pomet, whose work is currently in a Murakami/Juxtapoz-curated group show in Vancouver
https://images-na.ssl-images-amazon.com/images/I/51clijc%2B9UL._SY355_.jpg
Big Boat, the most recent album, was designed in-house by long-term band creative director/management member Julia Mordaunt, who is I believe the stepdaughter of a member of a smalltime New England jam band and Phish influence who plays with the bass player's side project
https://images-na.ssl-images-amazon.com/images/I/511zG6WKkZL.jpg
― Moo Vaughn, Sunday, 18 March 2018 18:15 (six years ago) link
five years pass...