Sinatra's Second Act

Benjamin Schwartz at The Atlantic:

Frank Sinatra, the greatest vocalist in the history of American music, elevated popular song to an art. He was a dominant power in the entertainment industries—radio, records, movies, gambling—and a symbol of the Mafia’s reach into American public life. More profoundly than any figure excepting perhaps Elvis Presley, Sinatra changed the style and popular culture of the American Century...

...the 1950s—more precisely, the period from 1953 to the mid-1960s—was clearly the era of Sinatra’s supreme artistic achievement and deepest cultural sway. It amounted to the most spectacular second act in American cultural history. In the early 1940s, following his break with the Tommy Dorsey band, Sinatra had emerged, thanks largely to swooning bobby-soxers, as pop music’s biggest star and a hugely popular Hollywood actor. By the end of the decade, he was all but washed up, having lost his audience owing to shifting musical tastes and to disenchantment over his reported ties to the Mob, and over his divorce, which followed a widely publicized affair with Ava Gardner, whom he married in 1951... But in 1953, his harrowing, Oscar-winning performance as the feisty, doomed Maggio in From Here to Eternity made him a star again.

More important, in that year he also signed with the trendsetting, L.A.-based Capitol Records, a move that afforded him his greatest role: his own musical and stylistic reinvention. The 16 concept albums that followed, his most remarkable achievement and among America’s enduring cultural treasures, defied public taste and redirected it toward what would be known as the Great American Songbook. With his key collaborator, the arranger Nelson Riddle, Sinatra jettisoned the yearning, sweet-voiced crooning of his Columbia years in favor of a richer voice, greater rhythmic invention, and more knowing and conversational phrasing. He had always said that Billie Holiday was his most profound musical influence, and at Capitol, accompanied by Harry Edison, the former trumpeter for Count Basie, he was even more deeply open to jazz influence, as he invested up-tempo songs with a tough, assured swing...