Not quite the same thing, but the movie Wrecking Crew covers a lot of backup musicians that made the 60s hits what they are, including Frank and Nancy's stunning Something Stupid and the drumming in Elvis' Vegas shows and music for his movies.
Read an interesting piece re Frank vs Bing Crosby who was much more successful than Frank - but Frank stays fresher, cooler. Tom Waits credits him for inventing the album concept in the 50's, forget which album, but the perfect one for making love (roughly that generation's Stairway to Heaven). Would be interesting to rate loss of virginity according to soundtracks throughout the years.

Edit: Tom Waits' complete list here.

Nice article!  In the early '30's, Bing Crosby and Russ Colombo were responsible for popularizing the Bel Canto style of singing.  Sinatra was the young kid who came along ten years later to usurp the title of King of the Crooners.   It's fascinating to compare all three.  Each had their strengths.   Sinatra's phrasing is impeccable and at times, even breathtaking.  I don't think you can overstate how much these three changed the style of singing in popular music. 

I was never a particular fan and never, before, had much of an opinion one way or another of him as a person, but here s a great tribute to Sinatra. 

https://consortiumnews.com/2015/12/13/the-complex-legend-of-frank-sinatra/