To understand his impact, look no further than the music streaming service Spotify, where 4.8 million people listen to his music each month. Not bad for a guy who has been gone now for two decades.
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Ole Blue Eyes is back in the public eye, but in the hearts and minds of his fans, Sinatra never really left -- which is why he remains such a constant presence.
"He was the greatest entertainer of the 20th Century by far," former manager Eliot Weisman said at Patsy's Italian Restaurant, a favorite haunt. "The place the man was happiest, center stage with a microphone, and a 30 to 50 piece orchestra blaring away behind him."
Weisman has written a new book about "The Way It Was," so that Sinatra's many fans can understand the guy the manager knew for a quarter of a century.
His music came from a mercurial nature, a personality split between light and dark.
"He had periods when he'd get depressed, and that was the dark side," Weisman said.
Weisman also got to understand Sinatra's relationships with others.
"If he was your friend, you didn't need any other friends," Weisman said. "If you crossed him, he'd go out of his way to try and irritate you, or worse."
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In his lifetime, Sinatra was often accused of mob ties, especially after a 1976 photo taken in Westchester showing him with notorious mob boss Carlo Gambino.
"I knew that picture was gonna come back to haunt all of us, and it did," Weisman said.
Years later, it's become part of the Sinatra mystique. His brand of cool has proven to be timeless, his way of interpreting a lyric could never be properly imitated.
"The way he carried himself, you knew he was in charge," Weisman said. "He was the boss. You can't teach anybody that."
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