I saw this picture in a 1940 yearbook and thought, “That looks a lot like Ol’ Blue Eyes, except for those jacked-up teeth.” Turns out it was Sinatra, and the best (teeth) were yet to come. The Chairman of the Board was not the big draw at the above 1940 Freshman Frolic; that honor went to Tommy Dorsey. Back in 1940, 25-year-old Frank was merely a “boy singer” in Dorsey’s band, earning sufficient funds to fix his teeth.
In fact, another six years would pass before Sinatra released his first studio album, The Voice of Frank Sinatra. He was lucky to get a mention in this partial review.
Don’t worry, Roscoe. He can’t put a hit out on you for saying this, although that does sound like his style. Confrontation he did not shy away from. And it was that spirit that sent him back for another round of dental work years later.
As Paul Anka recalls, a drunk Sinatra, upset that Sands Casino owner Howard Hughes had declined his credit, jumped up on a blackjack table and pitched a fit. When manager Carl Cohen tried to calm him down, Sinatra called him a “fat Jew bas****” and turned over a table. What could Cohen do? Turn the other cheek? Or punch him in the face and send Frank’s teeth flying across the room? He chose the latter.
“You may not realize it when it happens, but a kick in the teeth may be the best thing in the world for you”.–Walt Disney