Each guitar is different, serves a different purpose.
I own a '51 Gibson ES-350, and it's a great jazz guitar (not as good as an L5, Byrdland, or Super 400), and good for blues of the jump era, or backing a harmonica.
I have a 56 Reissue Gold Top Les Paul with P-90's. Great pre-war blues guitar, again backing a harmonica and that sort of stuff.
I have a 98 335 reissue. Nice guitar, beautiful blonde finish, but the tone isn't that great. I took out the stock pickups, which are extremely bright and replaced them with Seth Lovers, and that helped, but overall I've never been really happy with it.
I have a custom made strat, which I made myself with parts I bought. Not really that great for the sound I want when I play a strat. It can have it's moments though.
By far my favorite guitar is my 63 Epiphone Riviera. Prior to Gibson buying Epiphone, the company made some great guitars. This is one of them, along with Sheratons and a few others. Mine has mini-humbuckers. This is my first wife, similar to SRV's number one. Whatever I hear in my head and want to reproduce, this guitar will do it and at the drop of a hat. I just know how to manipulate it perfectly.
Certain guitars have a feel to them, like an old pair of shoes. Sometimes, you get a sound that you hear in your head, and no matter what you do you can't do anything to get a good sound from a rig, then hear a tape of the gig, and it sounds exactly how you wanted it-completely different from what you heard on the gig.