Jazz guitar has always fascinated me, ... and intimidated me too.
When I was first starting out on guitar, it was enough for me to grasp the minor pentatonic scales in a couple of positions. The feeling was incredible at first: just to be able to actually SOLO, play LEAD guitar! I used to record backing tracks of three chord rhythm parts for about five minutes on C90 cassettes, then 'shred' blistering solo's over the top. Well, that's not strictly true; I used to enjoy slow noodling really, playing little fills with the harmony always dominant.
It is an amazing feeling though, as most guitarists will probably tell you, when you first hear yourself creating your own signature within a track, making it up on the spot so-to-speak. I guess that's the spirit of jazz right there: improvisation.
I also fell in love with the Ionian scales and modes as I got more experienced, and this gave me an even greater ability to mindlessly fanny about on a guitar for hours on end. I know I haven't got the technical virtuosity of a Joe Pass, or George Benson, but I absolutely know I have a jazz heart.
Jazz has a sophistication and bohemianism that never fails to draw me in. It has it's very own mythology, codes, subcultures, genres. It is a smokey, nocturnal netherworld inhabited by junkies, existentialist's, crazy loners, Beat writers and poets - what Jack Kerouac would call 'The Subterraneans'.
Jazz guitar can be complex but its also got a danger to it, a constant stepping off (or jumping off) the path most travelled, and charting new paths, or just creating beautiful little improvisational moments of sound like sonic dada or Situationism.
Jazz guitarists like George Benson take up Heraclitus' proclamation that you can never step into the same river twice, everything is always changing and you must be prepared to change with it - take that old riff somewhere new.