I don't remember the exact moment I became a Sinatra fan. I started listening to his work in the early 90s, inspired by more contemporary singers who looked up to him than by any sense of music-history know-how. Having been raised to an eclectic diet of opera, Elvis, Abba, Olivia, and country gold (Cash, Jennings, and Cline, mainly), there was something vaguely ... dangerous about Francis Albert. I couldn't put my finger on it but his voice, even at its sweetest, had a hint of something that both scared and delighted me. Only many years later did I understand that quality to be sex appeal -not the smooth, suave, safe sort, but the rough-and-tumble variety, where passion came before pronouncements.
Sinatra never had to be smutty to seduce through song; it could be a slight pause, a tiny added grace note, a lingering phrase. He deeply understood how tied up creative power was with sexual power (and vice-versa), and he used it, grandly, carefully, proudly and loudly, as he got behind the wheel of The Great American Songbook, flashing a smile, a dark stare, a cocked eyebrow, cruising by, leaving a wispy trail of cigarette smoke in his wake, and enough baritone reverb to echo through eons. Since his passing that Songbook has been reduced to a series of pieces that are mere vehicles for a bland, safe, PC-style seduction, souped up in a red hot convertible and tinkling horn. Sinatra would never be so obvious.
Though he had an undoubtedly operatic approach, and knew a thing or two about a romantic tune, Sinatra's sound let in the darkness through time; his voice became full of shadow, of color, of subtlety and suffering and self-doubt. It reflected life experience, of course - and what a life it was. James Kaplan's exhaustive 2010 biography of Sinatra's early-to-middle years is a mighty tome that rivals Ulysses in sheer size and detail. Until Kaplan publishes the companion piece, we won't know about Sinatra's final years - but I have my own specific memories of today, involving comforting older women in a shoe store, whose lives, memories, and perhaps even passions, were so tied up with the man and his music.