@tablejockey: You are so right about Redd Volkaert (for those who don't know, Redd took Roy Nichols' place in Merle Haggard's band after Roy's passing, and won a Grammy in the 2000's for best instrumental performance). A bassist partner of mine and I drove to Austin in 2008 to look for a house to buy (we were going to hire ourselves out as a rhythm section to all the singer/songwriters in that town), and after checking into the motel went to a bar on 6th Street for a beer. There were a coupla amps and a drumset on the bar's small low stage, but no band playing. Turns out they were on break, and when they returned and the guitarist stepped on up who did we see? None other than Redd! A world-class guitarist, playing at a local bar when he wasn't on the road with Merle. That's a real musician.
Another Telecaster great is (or rather was) Danny Gatton, whom Vince Gill nicknamed "The Humbler". OMG what a player! Another is a guy who was a bandmate with Danny when they both lived in Virginia, Evan Johns (who did three albums for Rykodisc, and a bunch on smaller labels) I did an album with Evan in the late-90's in Atlanta (entitled Moontan), and during recording Evan told me Danny was the best musician he ever worked with. Danny never came West, so I never saw/heard him live. Evan's dead now too.
And how about Kenny Vaughan? He's been playing in Marty Stuart's band The Fabulous Superlatives for years now, but I first saw him live when he was in Lucinda Williams' road band. I saw/heard Al Anderson playing in NRBQ a coupla times, another favorite Tele player of mine. He left the band to concentrate on songwriting, lives in Nashville now.
When it comes to the Strat, we have to start with Richard Thompson (after Ry Cooder, of course ;-) !
But back to watches. I was in the band of a singer/songwriter who insisted no one wear a watch on stage. He wanted he and his band to look as far removed from everyday normal life as possible. Hey, the songwriter gets to write the rules ;-) .