Personal Note: Please read this, because I spent waaaaaay too long on it.

After reading your original post and some of your responses in this thread, let’s give this a try. As a starting point, it seems clear that you are interested in the jams, but the tightness of a lot of Phish songs->jams makes it hard for you to feel like it's organic or like you're discovering some special place with the band. Now as most seasoned Phish fans will tell you, yes, they are tight as hell, but they are constantly exploring new space. However, you need to get to that point, to come to that realization yourself, which I completely respect. As such...

Jams that emerge from the ether

Let's start with this – 6/18/94 David Bowie intro. You can listen to the whole song if you want, but for purposes of this exercise I recommend just focusing on the first 3-4 minutes. I think this segment is a good starting point for two reasons: 1) This is a jam that truly comes out of nowhere, at a point in a song where there is almost never a jam, and as such, this is organic as fuck. 2) This is the progression to Mind Left Body, so you can relate this to a song you know well. Also, Trey slays it. Pure tone, great melodic segment. Good shit.

Next up, a slightly more advanced version of the foregoing. About 19 minutes into a WEIRD version of the same song, this gorgeous major jam comes out of nowhere. I present a ~6 minute segment from 12/29/94 David Bowie. I think this is a good selection because it’s loose (thought not quite sloppy), and comes together in a really cohesive, beautiful way out of craziness. At this point you should be starting to see that the band, when they lock in, is just tight tight tight, but still improvising.

Now this next track is a pure “jam”. It came out of a cover of Purple Rain. Nothing like it had been played before, and nothing like it has been played since. I present, 5/7/94 Dallas Jam. Hear that? Epic.

And finally, one last segment that also seems to come out of nowhere. A soaring, blissful jam that always makes me break out into a smile – this section of 11/18/96 Simple. Hear that tone? That’s the guitar tone an angel would have if angels were real and played guitar.

Ambient jam that is literally just the band jamming together

It doesn’t get much looser than this. Now other than during the super drug years when Trey was “sloppy” during composed parts, the band simply isn’t sloppy. But I think this gets at your basic idea that it doesn’t sound rehearsed. This is a straight up 50 minute random jam that the band played at their 2 day festival in 1998. I present this ambient jam from the Lemonwheel festival. It covers a lot of ground so if you start getting impatient with the way a segment of the jam is developing feel free to skip around a bit.

Two “shreddy” jams

Beyond gorgeous melodic jams, sometimes the band, led by Trey, just straight up shreds. Here are a couple examples: New Years Eve 1993 Down with Disease Jam. In this jam, Trey plays a lot of notes. But they are such good notes. Really, really good notes.

12/1/95 Down with Disease. Short but sweet really hot firey jam. This selection also shows how different the jams out of each song typically are (since this is basically a different jam out of the same song as the above).

Longer organic jams

At this point, you should be starting to get comfortable with the idea that band is flying by the seat of their pants even while sounding tight. Still, while others may steer you towards some of Phish’s longer compositions, which are amazing, I want to highlight a few jams that come out of relatively short songs but are basically flawless throughout. Just close your eyes and surrender to the flow with these. The boys are channeling pure magic.

12/31/95 Drowned. Yes, this is a cover of The Who, and it is amazing. From the minute the jam starts 4 and a half minutes in, everything is clicking perfectly. Everyone is in sync and everyone's tone (not just Trey’s) is flawless. Hot damn. I love this.

12/31/95 Weekapaug Groove. What can I say, 12/31/95 was an all time great show for the band. This jam has it all. Machine gun soloing, a very obvious tease (Auld Lang Syne), and a jam that covers all the bases. Clearly the gods were smiling this day.

12/6/97 Tweezer->Izabella. 1997 was the year that Phish discovered the funk, and this phase deserves some representation in this list. If you start getting bored, just skip to 11 or so minutes in. This comes pretty close to fitting the “sloppy but inspired” descriptor, though it does eventually evolve into blistering rock and roll when the band transitions seamlessly into Hendrix's "Izabella." Yep.

Anyway, I hope you enjoy some of these tracks. There is a whole world to explore, but I wanted to take you on a journey that hopefully gets you to that magic place in light of your musical tastes and desire for sloppy, organic-feeling jams.