I think "best" is not a good angle to approach guitarists or any other musicians. To quantify all the things that makes musicians great and rank them on some phony scale is just not something I generally do. I'm more fond of "favorite" than I am of best, but all that aside ..
First off is an obvious mention perhaps, but you can't go wrong with the guitar trio - Al Di Meola, John McLaughlin and Paco De Lucia. Paco is generally described as a flamenco guitarist, but some of the music he's played is regarded as flamenco jazz. My favorite of the bunch is Al Di Meola. Everything about the way he plays is brilliant, I think.
For gypsy jazz, you'd have to mention Django, of course, but my favorite gypsy jazz guitarist is Jimmy Rosenberg who is just a ferocious player. In other jazz genres, I'd also like to mention Bill Frisell whose more ambient sounds I very much like and, although he's relatively unknown, I quite like the very much unique style of english jazz guitarist Phil Miller - for reasons that I sometimes wonder about. He played these squeaky melodies, but I always thought they sounded absolutely great in their musical context. He also was great with chords.
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Originally Posted by spiderhammer
Does Allan Holdsworth count as Jazz?
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Even if he's definitely in a style of his own, I think Allan Holdsworth counts as he's generally known as a jazz fusion guitarist. His presence really gave a lift to some records back in the 70s, like Soft Machine's Bundles, Gong's Gazeuse! and Jean-Luc Ponty's Enigmatic Ocean. Great player indeed!