Sinatra has, one could say, narrative ability. He turns a song into an intimate, seemingly autobiographical short story, usually a love story as told from the heights of romantic excitement (“I’ve Got the World on a String”) or the depths of romantic despair (“I’m a Fool to Want You”). At an academic conference devoted to Sinatra at Hofstra University in November 1998, the year of his death, Julius LaRosa (who sang on Arthur Godfrey’s TV show in the 1950s) chose Sinatra’s version of “I Get a Kick Out of You” to illustrate the singer’s narrative approach. “He sang the song not as it is written, not as a band or dance song, but as a song with a story to tell,” LaRosa said. On another occasion LaRosa remarked that Sinatra could “turn a thirty-two-bar song into a three-act play.”

It happened fast. In 1939 Sinatra began the year singing at the Rustic Cabin in Englewood, New Jersey. In the years since, maybe a million people claim to have heard him perform there. One person who really did hear him was handsome Harry James, of the mustache and trumpet, who signed the singer to a oneyear contract at $75 a week. With the James band Sinatra sang “It’s Funny to Everyone but Me” in August and “All or Nothing at All” in September. The voice was creamy, smooth, with a vulnerable edge. Sinatra, Pete Hamill writes, “created a new model for American masculinity,” and this was apparent from the start. So was the singer’s countervailing confidence, even defiance. James (whose signature song was “You Made Me Love You") wanted his new boy singer to change his name to Frankie Satin. Screw that. His mother would kill him. He was Frank Sinatra, and he would stay that way. Years later, when the subject of the proposed name change came up, Sinatra cracked, “If I’d done that, I’d be working cruise shins today.”

Sinatra is to singing what Brando is to acting. He doesn’'t just sing a song but live it.

“When Frank joined the band,” James said, “he was always thinking of the lyrics. The melody was secondary. If it was a delicate or pretty word, he would try to phrase it with a prettier, softer type of voice. … He could sing the wrong melody, and it would still be pretty.” By the end of 1939 Tommy Dorsey, “the sentimental gentleman of swing,” had heard Sinatra on the radio and hired him away from James for his own vastly more successful band. He raised Sinatra’s salary to $125 a week. Sinatra would replace Jack Leonard, a fine crooner (“Marie,” “In the Still of the Night”), who had left the Dorsey band to strike out on his own and had flopped. Sinatra had just turned 24.


Sinatra hated leaving the James hand. The last night was in Buffalo in January 1940, and Sinatra never forgot it. “The bus pulled out with the rest of the guys after midnight. I’d said goodbye to them all, and it was snowing. I remember there was nobody around, and I stood alone with my suitcase in the snow and watched the taillights of the bus disappear. Then the tears started, and I tried to run after the bus.”

At a party, I was having a conversation with a friend about our favorite Sinatra songs. I chose “I’ve Got You Under My Skin” (1956), and he countered with a different Cole Porter tune, “At Long Last Love” (1957), although he said he was tempted by “I Get a Kick Out of You” (1953), because of Sinatra’s marvelous riff on the final you , or “Night and Day” (1957), which has another of those amazing Sinatra moments, when he stretches the word through in the phrase “and this torment won’t be through / until you let me spend my life making love to you.”

What do all four of these songs have in common? They were composed by Cole Porter, whose urbanity and wit made him perhaps the ideal composer for Sinatra, with Richard Rodgers of Rodgers and Hart a close second, followed by George Gershwin, Duke Ellington, Harold Arlen, Jerome Kern, and Irving Berlin, possibly in that order. Sinatra is the exemplary interpreter of the great American songbook because he can shade his emotions. His joy is edged with irony and also sometimes with rue, melancholy, and something more, a heartbreak bred in the bones.

Perhaps even more important, all four songs were arranged by a former trombonist with the Dorsey band, a genius named Nelson Riddle. Working with Riddle was one of the best things ever to happen in Sinatra’s career. Riddle helped define the Sinatra sound during the eight years he sang on the Capitol label, the period of his best work, 1953 to 1961. If you’re a newcomer to Sinatra, I recommend beginning with The Capitol Years , a three-CD anthology set, and then going on to these indispensable individual albums, all of them with Riddle arrangements: Songs for Swingin’ Lovers!, In the Wee Small Hours, A Swingin’ Affair, Swing Easy, Nice ’n’ Easy, Only the Lonely, Close to You .

Will Friedwald: “It remained for Riddle to develop both the ballad side and the swinging side of Sinatra, or rather to extend the legacies of Axel Stordahl and George Siravo and, before him, Sy Oliver. And the Sinatra-Riddle sound has since become what we think of when we think of Sinatra; the pre-Riddle period can be reduced to a prelude, the post-Riddle era to an afterthought.”