Fender strat without question. And specifically the one Hendrix played at Woodstock. And then its a toss up between Tele and Paul but probably Paul. I'm a biased Fender guy.

:bowdown: For me it would have to be this one. Really just a gorgeous instrument.

I've heard that a good guitar can actually improve with age, but can a guitar with a hole in it help but sound at least slightly ****ty, no matter how aged-to-perfection it is?

Gonna throw this on the pile:

http://assets.rollingstone.com/asset...1373310472.gif

I personally cream at a unique sounding guitar that some might call ****ty so I'm kind of biased when I say it helps. It's a case by case basis that depends on a lot of things like the shape of the guitar, size of the hole, type of wood, where the hole is, etc. In Nelson's case it worked out.

...and this. Every shredder from the late 80's/early 90's wanted this:

http://www.vai.com/site-images/tm/originalpromo_87.jpg

I always thought the handle was a stupid gimmick, but a pretty cool stupid gimmick at that.

It's ergonomic.

While I'll jump at any chance to root for the Telecaster, being a biased Tele player myself, I don't think I'd be stepping out of line claiming that it may have been the most iconic guitar during the birth of rock and roll and the evolution of the electric blues. Muddy Waters is often credited as the godfather of the electric blues and possibly rock and roll, getting his first electric in 1945 and becoming one of the first blues musicians to regularly utilize the electric guitar in a full band configuration.

http://i.imgur.com/vG5tymO.png?1

The Rolling Stones, one of the first bands to really define rock music as it's own genre.

http://i.imgur.com/9xAUQcf.png

The Kinks, one of the first bands to really popularize distortion in rock music.

http://i.imgur.com/xz9haGp.png?1

Eric Clapton's Yardbird's / Blind Faith days.

http://i.imgur.com/zOYgW5O.png

Led Zeppelin's early days.

http://i.imgur.com/mhJogiI.png?1

That being said, many of these early Tele players picked up Les Pauls and Strats in the early 70's when rock music became more visceral.