Pete Drake and His Talking Steel Guitar
Via BoingBoing, this is one of the few things I've ever seen called "Lynchian" that truly lives up to the concept:
The song, "Forever," is actually quite good. According to the comments and Wikipedia, Drake was a big session player in Nashville during the sixties (this track dates from 1964), and the talk box technology he's using dates as far back as 1939! Like a lot of TV appearances, it seems this was a lip-synch job. I don't know what the TV show is nor the identity of the emcee.