Sinatra 10 years Later: To Young Stars, Ol' Blue Eyes Is an 'All-Timer'

As Bono once observed, Frank Sinatra didn't care much for rock music. But the U2 frontman spoke for many baby-boomer pop stars when he added, "The feeling is not mutual. Rock 'n' roll people love Frank because Frank has got what we want: swagger and attitude."

Now, 10 years after Sinatra's death (on May 14, 1998) at 82, the charts are littered with artists who hadn't yet launched careers by the time Ol' Blue Eyes shuffled off his mortal coil. To these performers, most of them in their 20s and early 30s, Sinatra is surely a relic of an ancient era: a booze-swilling, pinkie-ring-wearing crooner who just happened to cover many of the great American songbook's greatest songs before Rod Stewart got his chance to have at them.

Guess again.

"Frank Sinatra is an all-timer, the true definition of class and style," says Alicia Keys, 28, who in February performed a virtual duet with Sinatra on "Learnin' the Blues" — singing and playing piano while accompanied by footage of the late superstar — to commemorate the 50th anniversary of the Grammy Awards.

Rising singer/songwriter Sara Bareilles, also 28, says Sinatra "helped define a genre that I believe will be a staple of popular music forever. He is as 'cool' as it gets."

"He was always an icon to me," says John Legend, 29. "I always thought of him as one of the great singers. His voice was distinctive and magical."

John Mayer, 30, says he's "only now realizing how sophisticated (Sinatra's) work was." In fact, he's "seriously thinking about (making) my next album" a homage to 1955's "In the Wee Small Hours," one of Sinatra's classic collaborations with conductor and arranger Nelson Riddle.

Such admiration may seem ironic, or anomalous, at a time when many singers represented on commercial radio and "American Idol" appear more concerned with flaunting their technical prowess than mining the sometimes subtle emotions embedded in lyrics and melodies, whether their own or someone else's. Sinatra, who in concert was famous for introducing and praising songwriters, took the opposite approach: He always believed in the singer serving the song, rather than vice versa.

"The rock-bottom basis of Sinatra's fame was his extraordinary interpretive talent, his way of connecting with a lyric," says veteran musician and music historian Michael Feinstein, who worked with Sinatra and plans to release his own tribute — "The Sinatra Project," a collection of new interpretations of classic Sinatra tunes — in September. "He held the music, and the way it was performed, sacred."

Feeling the phrasing

If that reverence isn't shared by all contemporary singers, it's clearly appreciated by some high-profile representatives. "You felt every word he said," Keys says. "I appreciate his phrasing the most." Mayer, too, cites Sinatra's rhythmic intuition: "When you sing along to a Frank Sinatra record, you're always a little early in singing the words, you know? His delivery was so soulful."

Pop baritone Josh Groban, 27, considers Sinatra "the ultimate song stylist. He was telling stories with songs. He showed it was OK to let different nuances come through. No one has sounded like him before or since, and that's something every young artist would want to strive for."

But Sinatra's enduring influence, as Bono suggested, isn't purely musical. Says Keys, "He definitely had an impact on contemporary artists well beyond music — from his fashion sense to his 'crew,' the Rat Pack."

Season 6 "Idol" runner-up Blake Lewis recalls watching that legendary crew — Sinatra, Dean Martin, Sammy Davis Jr. and a few other buddies who held court in Hollywood and Las Vegas in the 1950s and '60s — "in classic movies" as a child and admiring Sinatra for his "camaraderie with his chums" and "because he seemed to have fun every time he took the stage. This is what I try to emulate."

Indeed, despite Sinatra's disdain for rock — which didn't, incidentally, prevent him from performing songs by George Harrison or recording duets with Bono and Chrissie Hynde — he arguably created the prototype for the modern pop star. Years before Elvis Presley, Sinatra appropriated African-American music (jazz, in Sinatra's case) for mainstream audiences that included swarms of swooning girls. Decades before Madonna, Sinatra started his own record label, Reprise, which spawned numerous name artists.

Singer/songwriter Gavin DeGraw, 31, notes that another jazz-based icon, Bing Crosby — one of Sinatra's idols — already had "the album sales and movie sales" that are "the criteria for pop success."

But DeGraw concedes that Sinatra "carried Bing's torch further into our contemporary culture," helping to "portray the artist as a man with a lifestyle, not just a performer. Our pop stars' private lives and lifestyles have become the main ingredient in most of their careers."

And just as Sinatra's singing, particularly from the '50s on, conveyed greater depths of sensuality and experience, his public image became more complicated, and more controversial. By various accounts, he loved women and liquor lavishly, if not recklessly. "And of course, there were rumors of him being connected to the Mob," Legend points out.

"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?"

If Sinatra had been a fledgling artist in 2008, "he would have been influenced by whomever came along today, just as he was shaped by Bing Crosby and Al Jolson and Louis Armstrong and other influences he heard as a kid," Feinstein says. "And he would have taken these new influences and, as he did with the older ones, moved them to another place."

And were Sinatra alive and recording, he might still be learning the blues — and teaching them. "I was at Sinatra's house for dinner one night when Dean Martin was not well and had stopped singing. And Frank said, 'They're going to have to put me in a box to get me to stop singing.' "

His music lives on

Radio personality Jonathan Schwartz — the son of traditional pop composer Arthur Schwartz, whose material Sinatra covered — knew the Chairman of the Board even longer, and insists, "Sinatra hasn't gone anywhere. He's still profoundly alive." His music "proliferates" on Schwartz's programs, simulcast on New York's WNYC and XM Satellite Radio, "and I feel that music is more deeply perceived than ever."

Schwartz won't speculate on how Sinatra, given his professional savvy and penchant for trailblazing, might have embraced new opportunities offered to musicians by the Internet and other changes in the music industry. Still, he notes, "there are massive displays of his (work) in stores that sell CDs. You can go online and find discographies that list the dates of each and every song he recorded. If you go on YouTube, you'll find him singing everywhere.

"He is born again and again every day. Just go outside and listen — you'll hear him."