A number of years ago a co-worker me asked me what swing is exactly. Taken aback a bit at first, I realized that for Boomers and younger, swing was never a popular form of music (and, no, the LA "Swingers" revival of the '90s doesn't count). But after a little thought I recommended the classic Billie Holiday sides with Lester Young et al. as the essence of swing. But now whenever I think about her question, and I still do, I think the best, most efficient way to start a journey into swing would be to listen to Frank Sinatra sing "Fly Me to the Moon" with the Count Basie Orchestra in 1964.
It has all the necessary elements: the walking bass moving up and down through the chord changes right on the beat, the light bouncing feel, the hip syncopation, the crescendos and decrescendos from the band. Fun fact: This arrangement was created by Quincy Jones, who was a full-bore jazzer in his earlier years. When Q finally connected with Michael Jackson, it's safe to say he knew about star power.
Watching the new HBO documentary "Sinatra: All or Nothing at All," I gained more appreciation for Sinatra's life and career. A kid from Hoboken, he was a working pro by the age of fifteen and never even finished high school. I knew he was an idol and sex symbol for the bobby-soxer girls, but I never realized that the mania was equal to Elvis and the Beatles. Ultimately, the heartbreaker got his own heart broken in the 50s by Ava Gardner, and his music took on a deeper, jazzier, hipper tone -- the Sinatra that lives in our imaginations. Personally I have a hard time seeing what all the fuss was about prior to this time.
Back to this business of swing falling out of favor. It's not just that the new generation in the 60s was indifferent to the music (other than blues and folk) that came before it (since everything was felt to be "new" and "unprecedented"), but that Sinatra was actively hostile toward rock. A man of incredible taste, he just couldn't appreciate the hippies -- at least in the plural; he did marry Mia Farrow after all. The upshot is that by the time the 1970s came around, everything Sinatra stood for was ripe for Bill Murray's devastating Saturday Night Live parody of an unctuous lounge singer.
In time, all things merge, and led by the late career success of the great Tony Bennett, who was never hostile to anyone, people of all generations came to love Sinatra and his new-era acolytes like Michael Buble' and Dianna Krall. Now that the dust has settled, I'll argue that Sinatra is the true King, not Elvis. The proof is in the singing.