AT A PARTY a friend and I were having a conversation about our favorite Sinatra songs. I chose “I’ve Got You under My Skin” (1956) and he countered with “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 maybe “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? All were composed by Cole Porter, whose urbanity and wit made him perhaps the ideal composer for Sinatra, with Jimmy Van Heusen a close second, followed by Jule Styne, the Richard Rodgers of Rodgers & Hart, George Gershwin, Harold Arlen, Jerome Kern, and Irving Berlin. Sinatra is the exemplary interpreter of the Great American Songbook because he can shade his emotions: his joy is edged with irony and sometimes with rue, with melancholy, and sometimes something more, a heartbreak bred in the bone.
Perhaps even more important, all four songs were arranged by a former trombonist with the Dorsey band, a genius named Nelson Riddle. Riddle was one of the best things that ever happened to Sinatra. During the singer’s eight years on the Capitol label, the period of his best work (1953–61), it was Riddle who defined the Sinatra sound. 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.
Critic 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.”
Oh, yes—you wanted to know the meaning of “swing,” the word that recurs so often in Sinatra’s album titles? Listen to “All of Me” (music, Gerald Marks; lyrics, Seymour Simons) on Swing Easy (1954). This is a song Sinatra had frequently sung in the 1940s, each time experimenting a little more with the phrasing and with how he exits from the song. Here he sings the final stanza with such exuberance as to undo the actual sense of the words. Where the line as written would require him to sing, “can’t you see / I’m no good without you,” he sings “can’t you see / I’m just a mess without you.” The emphatic “mess” sounds more like a triumphant declaration of independence than like a suitor’s plea. The lyrics say one thing, the delivery says another, and the style makes it cohere. That’s one way swing works.