Bad Sneakers Steely Dan
I know: Donald Fagen looks like an aging vampire and his voice has one of the weirdest registers, somewhere between your low-rent aunt with the smoker's cough and Woody Allen impersonating Ray Charles. But he is what he is; it's hard to find any trace of pretentious affect. He has that cool that only comes from not caring about being cool, from knowing that to try to be cool is to achieve being a fool, and it's hard to imagine anyone else singing his songs with convincing conviction.
When one adds to this the pearly luster of the band performing the song live and sounding better than the studio, what remains is Walter Becker's guitar solo. His sound straddles the divide between the wild tone of a vintage Stratocaster and pure jazz clarity.
For early photographic proof that Donald and Becker (the two on the right) were, if anything, so anti-hipster that they were literally too cool to be uncool, look at this photo from the early days of Dan: