"From all the stories you hear, he was a tough guy," Mayer says. Landon Pigg, 24, another troubadour and Sinatra fan, has gleaned that as "generous as he may have been with his friends, (Sinatra thought) the world revolved around him."
None of that diminished his influence. "Whether leaving the label that was largely responsible for his success to begin a label of his own, successfully wooing four wives or drinking a greater percentage of alcohol than the annual precipitation of Los Angeles," says Pigg, "Frank helped to define the pop-star cliché as we know it today."
Hip-hop hero
In recent years, Sinatra's raw charisma and edgy glamour have fascinated the hip-hop community in particular. Jay-Z, 38, has called himself "the Sinatra of my day" in his lyrics; Ne-Yo, 25, is a "big fan."
"He's got an image that so many rappers appropriate," Legend says. "He was part of the establishment, but rebellious at the same time. You knew this was a guy you didn't (mess) around with."
One of Legend's favorite tracks is a "mashup" of recordings by Sinatra and the late Biggie Smalls, aka the Notorious B.I.G., called "Everyday Struggle" or "Blue Eyes Meets Bed Stuy." "If you have any doubts about Sinatra's effect on hip-hop, you have to check that out."
Jazz guitarist, singer and composer John Pizzarelli, who toured with Sinatra later in his life, says Sinatra had a more fundamental flair that all young pop stars can appreciate, a quality shared by great vocalists and inveterate ladies' men — by no means mutually exclusive groups. When Sinatra sang, "he could convince you that he was the guy without the girl — even though, of course, he never was," Pizzarelli says. "If he were still around, everyone would still be kneeling to him."
Tony DeSare, another jazz-influenced singer/songwriter who at 32 is a more obvious inheritor to Sinatra than most of his pop peers, says "it's hard to know what would happen" to a young artist who might come along today with Sinatra's particular gifts.
"The climate is so different," says DeSare, whose recent stint at New York's Cafe Carlyle drew George Clooney, Stella McCartney, Kate Moss and Victoria and David Beckham, all in one night. "Would he be a cabaret singer, or would that tremendous personality and talent still make him a mega-star?"