Not a fan of any of these guys but I love their guitars:
Trigger - Willie Nelson
He's had it forever and will keep it forever and that's why it's a sweet guitar.
Frankenstrat - Eddie Van Halen
Eddie made it himself and it's been on multiple world tours which is why it's awesome.
Most of Woody Guthrie's guitars
Legendary because he almost always put "This Machine Kills Fascists" on his guitars. It's punk before punk, protest rock before protest rock, Dylan before Dylan.
And that little phrase instantly makes most guitars sound better.