I'm going to have to chime in and say "all of the guitarists who can play like they SOUND like they're making 'mistakes' but are purposely playing loose and can also take control when they need to." To me it seems that requires an alternate level of "cleanliness", it's not metronomic and one-sided, it's all encompassing, and I think that's what makes those players unique, as well.
A lot of the players mentioned here are amazing guitarists, but I wonder if they could really break off of the metronome and loosen up for a while, and then go back to playing technically.
I really admire the players like Fripp and Howe (Steve) who can do both; convince you that they've only been playing guitar for a week, and then on the next track, or even a moment later in the same track, do things that don't even seem possible on a guitar, cleaner than seemingly possible (with no hair ties or "hands-over", either!). Holdsworth does it pretty excellently, too, especially on the older I.O.U., Velvet Darkness, Soft Machine, etc. stuff.
He's the cleanest sounding guitarist out there IMO.
AAAnd then there's this guy known as Alex hutchings. He's just amazing in general. He has some of the best sounding phrases and he just tames that guitar like a smooth butt!
Lol i was about to post that but you beat me to it, and hell yes Jason is definitely my pick, i'm hoping to get a lesson with him next time he's doing online lessons