The guitar that has taken me a long time to come to like is the Strat. I was too young to catch Buddy Holly, but a lot of the early-60's Surf guitarists played a Strat, and I had all The Ventures and Astronauts albums. Then it kind of disappeared until Hendrix appeared (hope I'm not forgetting anyone in between. Wouldn't want to make any more ridiculous statements ;-). I don't really care for Jimi's tone (that's being polite---I actually really dislike it. His playing as well, but I won't go there), finding it too "barbed-wirey", if you know what I mean (it sounds to me the way chewing on tin foil feels).
The Strat sound seemed to be kind of in between the thin, no sustain single-coil sound of the Tele, and the thicker, lots of sustain Humbucker sound of Gibson's, etc., having neither the charm nor character of either (I did however appreciate it's versatility). But so many of my favorite guitarists (Ry Cooder, Richard Thompson, even Robbie Robertson after being a Tele player for so long, to name a few) played a Strat that I just accepted it.
It has taken until fairly recently for me to be won over by the Strat's own subtle personality, but I finally get it. It's still a Fender, not providing much help to it's player or obscuring his lack of technique, style, or ideas. But, in the hands of the right player, is a very expressive guitar. I just love that chimey, harmonics-overtone sound that can be coaxed out of it's upper register!
