@stuartk: For me, the Telecaster starts with James Burton. He made a huge impression on the very young me, smiling as he stood behind Ricky Nelson on The Ozzie & Harriet TV show. His solo on Ricky's "Young World" is a favorite of mine, and George Harrison's solo on "Nowhere Man" sounds like it was modeled on the YW solo.
Steve Cropper was the second Tele player for me, his playing on "Green Onions" as good as it gets (good songwriter, too). I had that song as the ring tone on my cell phone for years. It always got a great reception from those who heard it playing on my phone in public. ;-)
As for Brad Paisley: As talented as he is, I have to admit I have mixed feelings about his playing. I take very seriously the notion of the musician's priorities as being in service to first the song, second the singer, third the ensemble, and lastly his instrument. I'm not sure Brad sees things that way.
It's interesting how the guitar a guy has in his hands affects his playing. For years Dave Edmunds was an ES335 player (he has two dot-neck 58's!), and when he switched to a Tele it just wasn't the same. I witnessed that with Bill Pitcock IV (Dwight Twilley's guitarist) too.
I lived in San Jose when Robben Ford moved south (from very northern California) with his brothers, stopping in town for a coupla years and playing around the Bay Area. The bassist in my senior year High School band joined The Charles Ford Band (named after the boys father) for a while, so I saw Robben live a lot. All the San Jose guitarists had to re-evaluate their playing after seeing Robben live ;-) . He worked with Charlie Musslehite for a while, playing a 335 back then. Next thing I knew he had moved to L.A. and was playing with Joni Mitchell, then Miles Davis. All it takes is talent.