Perhaps Kelly mentions this, but Sinatra was desperate to be Bogart.
Bogart and his buddies were the original Rat Pack; Bacall coined the name.
After Bogart’s death, Sinatra courted his widow, and worked very hard to manufacture his own “pack.” If he hadn’t been so cool — and he was in, as Kelly notes, his own way — this self-conscious effort at gang-building (there were even rules) would have gone down like a goofy kid trying to get a nickname to stick, or form a doomed garage band or cook up some similar scheme in a Stand By Me type treehouse.
Sinatra pulled it off and the Rat Pack remains the epitome of cool for millions.
Hell, I buy it and I know all about his awfulness (as well as his legendary if mercurial generosity.)
As I said in a post of my own, Sinatra is one of those people who I’d probably forgive a Manson-style killing spree, figuring the victims probably asked for it.
He really really really could sing.