Jumping off from the comment section:
A superb collection of images, inspired by this legendary paperback:
Example: Joey Bishop sings C&W – in an ill-fitting cowboy hat that he tilts at a rakish angle, as if he were his buddy Sinatra wearing a fedora.
“Joey not only can’t sing, he hardly even tries. His whispery, tentative voice is barely there … It’s like listening to a Ray Price concert, except that Price’s microphone has accidentally been set up at a dark corner table where a depressed, nebbishy accountant is drinking double martinis and singing along halfheartedly to the sad music to take his mind off the fact that his date didn’t show up.”
That book is a great read, by the way, and you can buy it for five bucks! (I have my own well-worn copy.)
Hollywood Hi-Fi update (it only took 16 years!)
Very entertaining: The Hollywood Hi-Fi Facebook Page