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THE LINKAGE OF Sinatra and Marlon Brando at the top of the ticket in Guys and Dolls marks a confluence too rich to go unremarked, because Sinatra is to singing what Brando is to acting: a performer who doesn’t just sing a song but lives it. I am not the first to say so. Pete Hamill: “He inhabited a song the way a great actor inhabits a role”—the way Brando inhabits the roles of Stanley Kowalski in A Streetcar Named Desire, the rebellious biker in The Wild One, Terry Malloy in On the Waterfront, and Don Corleone in The Godfather. “One of the writers at the time [the 1940s] said, with more than a touch of condescension, that Sinatra sang those love songs as if he believed them,” Gene Lees reports. “But of course. That was the secret. And far from manifesting a callow gullibility on Sinatra’s part, this was a striking advance in the art of singing.”

Take “One for My Baby (and One More for the Road),” the music by Harold Arlen, the words by Johnny Mercer, as recorded by Sinatra in June 1958. It was written for Fred Astaire, who introduced the song in the movie musical The Sky’s the Limit in 1943. Listen to Astaire do it. It’s good. It’s damn good. Mel Tormé lauded Astaire as a terrific jazz singer, and he wasn’t kidding. Or listen to Perry Como do it, or Etta James, or even Ella on her Harold Arlen Songbook. Both the song’s composer and lyricist recorded the song; they both sang well, and it’s a special pleasure, always, to hear a songwriter sing his own tune. Arlen called it a “wandering” song, a “typical Arlen tapeworm,” a “tapeworm” being industry slang for any song exceeding thirty-two bars. “One for My Baby” is half again as long, at forty-eight bars.

“One for My Baby”: the singer embodies the role.

Sinatra not only sings but acts the song. He becomes, for the next four minutes and four seconds, a guy whose girl has just left him—left him in the rain with an extra train ticket, stood up like Rick Blaine at Paris’s Gare de Lyon train station in Casablanca, feeling as if he’s just been punched in the gut. On television, Sinatra sings it in raincoat and fedora, dressed just like Bogie. He enters a bar, takes his stool, corners the bartender. It’s just before three in the morning, and the place is empty except for the two of us, so set ’em up, Joe, you’ve got to listen to me spill my guts. This glass is going to get me through the night.

Throughout the song, the bartender is silent, “true to his code”—the perfect listener, part witness, part therapist, part priest. The song promises to tell “a story,” but the details are vague. The singer never does explain exactly what happened. This is deliberate. The song can apply to any romantic postmortem. Also, how much coherence should we be expecting from a guy who’s half soused?

Sinatra sings to the piano accompaniment of Bill Miller. The piano sounds distant. Otherwise there is silence, except for soft strings when the first chorus concludes, and that broken saxophone solo near the song’s close. When Sinatra sings it on television, the main props he needs—besides bar, bar stool, and bartender—are a cigarette and ashtray. Without taking off his hat and coat, he takes his seat and gives Joe his order. He lights a match when beginning the line “We’re drinking, my friend” but doesn’t bring it to the cigarette until he gets to the “end of a brief episode,” which I cite because the phrasing here—the rubato—is exemplary. The words convey that he is a friendly drunk, alternately self-pitying (lamenting a too-“brief” love affair) and self-glorifying (describing himself as a “kind of poet”). Mercer’s lyric entrusts him with a dead metaphor brought violently to life, a “torch” that must be “drowned” or it may “explode.” Otherwise he drifts, as a drunken man might, into sentences that come to a period but lack true closure: “Well, that’s how it goes.” The music is subtle enough for Sinatra to sing it as if he’s having a conversation with you. He sings softly, in a way that approximates speech but remains utterly faithful to Arlen’s melody. The lyrics are the words of the last man standing at the bar.

Is it a stretch to compare our experience of the song with that of the Hemingway story set in a Madrid café at closing time, “A Clean, Well-Lighted Place”? The waiters are exchanging a few words on shutting down the place. First they have to shoo out an old man who has been drinking brandy. The old man had tried to kill himself the previous week. “Why?” “He was in despair.” “What about?” “Nothing.” “How do you know it was nothing?” “He has plenty of money.” One of the waiters is unselfconscious and goes his merry way, but the more sensitive man, the one whose mind we enter, lives in a condition of terminal religious doubt. In this famous riff, Hemingway uses the Spanish word for “nothing” to subvert the Lord’s Prayer and the Hail Mary: “Our nada who art in nada, nada be thy name thy kingdom nada thy will be nada in nada as it is in nada. Give us this nada our daily nada and nada us our nada as we nada our nadas and nada us not into nada but deliver us from nada; pues nada. Hail nothing full of nothing, nothing is with thee.” As a stay against confusion, a shield against the force of that “nada,” the waiter has the café where he toils, which is, at least, a “clean, well-lighted place.”

This song, that story, and the image of Bogart in the rain at the Gare de Lyon station—this, you might say, is what American existentialism, as a mood or an aesthetic condition, is all about.

In my favorite of several excellent studio takes, Sinatra ends “One for My Baby” by not ending it. Instead of the terminal phrase (“that long, long road”), he fractures it into fragments of farewell (“the long,” “so long,” “the long,” “very long”) trailing off into a never-ending ellipsis . . . (In the TV appearance, he sings only “the long . . . ,” then walks off into the dark.) I am not sure why he changes Mercer’s “dreamy and sad” to “easy and sad” as adjectives to modify “the music,” but that is a query not a quibble. The crucial thing is the sensual way he stretches the “ea” of “easy.” (Maybe his fondness for “easy” goes back to his treatment of “uneasy in my easy chair” in “It Never Entered My Mind,” which he recorded three years earlier.) In 1947 he sang “One for My Baby” in B-flat ascending to D. Now, ten years later, despite the darkening of his voice, he raised it up to C and E, a whole tone higher, with the effect of accentuating the fragility of the singing. You will find the song on the 1958 album Only the Lonely, arrangements by Nelson Riddle. “One for My Baby” was the last song on the record and the highlight in a group of saloon songs that includes “Angel Eyes,” “Good-bye,” “Blues in the Night,” and “Guess I’ll Hang My Tears Out to Dry.” But the version to get is the previously unreleased take on the three-CD set The Capitol Years (1990).

Only the Lonely: the clown on the album cover is a self-portrait of the singer with a pink tear flowing from a sparkling blue eye. The first time Sinatra won a Grammy, it wasn’t for singing. It was for the cover design of Only the Lonely.