In the summer of 1966, Frank Sinatra passed a baton to Bob Dylan. Not literally, of course: it’s hard to imagine, at that point in their lives, the two men being in the same physical space. Sinatra had been the most important figure in American popular music for twenty-five years: from his bobbysoxer days with the Tommy Dorsey Orchestra in the early 1940s, through wide-ranging Columbia recordings under his own name, and finally through a remarkable series of LPs with Capitol and then Reprise. Those records of the late 1950s and early ’60s — and Sinatra’s appearances on television and in nightclubs — redefined the jazz concepts of “hip” and “swinging” for the broader culture.
But things were changing. It’s hard to be a swinger at fifty-one; you can get a sense of Sinatra’s struggle to keep up in Gay Talese’s 1966 Esquire profile, “Frank Sinatra Has a Cold.” His recording career was in a valley; he hadn’t released a top-ten single since “Witchcraft” in 1958. That’s a somewhat unfair statistic, since Sinatra’s main success had been with LPs for a decade or more, but his most recent album, “Moonlight Sinatra,” had more or less tanked, peaking at number 34 on the charts.
His follow-up was a different story: a single and an album, which shared a title, shot to number one and stayed there for weeks. But popularity came at the price of currency. To young listeners, “Strangers in the Night,” with its improvised “doo-be-doo-be-doo”s, came off as irreversibly cheesy. (Sinatra’s follow-up, “Somethin’ Stupid” — a duet with his daughter Nancy — was even worse.) The man nicknamed The Voice still had at least a couple of decades of fine singing left, but, post-“Strangers,” he would never again be considered hip.
Bob Dylan pretty much defined hip in the summer ’66 — and, as with Sinatra, there’s a document of his persona at the time, the cinema verité “Don’t Look Back.” His new album, the double LP “Blonde on Blonde,” was truly sensational, with a series of incandescent songs — “I Want You,” “Rainy Day Women #12 & 35” (with its refrain “Everybody Must Get Stoned”), “Just Like a Woman,” “Visions of Johanna,” and many more — that were like nothing any musician had previously written or produced.
“Strangers in the Night” and “Blonde on Blonde” were different in performance, instrumentation, and song structure, but one difference most starkly underscored the changing of the guard. Sinatra, in keeping with the earlier model of which he was the incarnation, hadn’t written any of the songs on the record. Dylan, in keeping with the new model that he and the Beatles had jointly introduced, had written all of the songs on his. Up through “Tempest” in 2012, that has been the case on all his albums, with two notable exceptions. His debut, “Bob Dylan,” was filled with traditional songs plus a few written by fellow early-‘60s folkies. The 1970 “Self-Portrait” was an experiment in cover songs, alternating between country-and-western classics (“I Forgot More than You’ll Ever Know”), Everly Brothers-style rockaballads (“Let It Be Me”), and compositions by fellow singer-songwriters (Paul Simon’s “The Boxer,” Gordon Lightfoot’s “Early Morning Rain”). There was one Tin old-line standard, the Rodgers and Hart chestnut “Blue Moon,” but it was likely there because Elvis Presley had covered it in 1960. Otherwise, aside from a few one-off cover songs he released over the years and the two folk albums he released in the 1990’s, (“Good As I Been To You” and “World Gone Wrong”) Dylan sang Dylan. Period.
In interviews, Dylan was generally disdainful of the Tin Pan Alley model that had prevailed since the turn of twentieth century — a songwriter turning his or her work over to singers and bands. By definition, it lacked the personal authenticity and conviction that lay at the heart of the new musical credo. In 1991, talking with Paul Zollo,) Dylan was caustic about the music that came over the radio when he was growing up:
“Like, you know, all those songs on the Hit Parade are just a bunch of shit, anyway…. You know, ‘If I give my heart to you, would you handle it with care?’ Or, ‘I’m getting sentimental over you.’ Who gives a shit?”
Dylan’s new CD, “Shadows in the Night,” therefore represents a true sea change. He didn’t write any of the ten tunes on it, and a lot of the lyrics aren’t much better than “I’m getting sentimental over you.” Try this from “Full Moon and Empty Arms” (1945): “The moon is there for us to share/But where are you?” Those last three words are the title of another track on the disk, a 1937 number with lyrics by Harold Adamson and music by Jimmy McHugh that contains this triplet: “Where’s my heart?”/Where is the dream we started?/I can’t believe we parted.”
Frank Sinatra made “Where Are You?” the title track of a 1957 Capitol LP, and, in fact, the thing that links the ten songs on “Shadows in the Night” is that Sinatra recorded them all. Dylan’s title, with its surely deliberate echo of “Strangers in the Night,” emphasizes the disk’s engagement with the earlier singer. To be sure, “Strangers in the Night” isn’t on it, nor is anything remotely uptempo or upbeat: the closest is the closer, a rousing “Ol’ Man River” descendant called “That Lucky Old Sun” (a bigger hit in 1949 for another Frankie — Laine). Otherwise, this is the Sinatra we spy under the streetlamp, the last man still drinking at the bar, the Sinatra of loneliness and despair. Such, of course, has more or less been Dylan’s musical mood from “Time Out of Mind” in 1997 through “Tempest” in 2012. And what better backdrop than sweet melancholy for the rapprochement, half a century on, between these two titans of American music?
In his admittedly scattershot public comments over the course of his career, Dylan has barely mentioned Sinatra at all. (The comment about “I’m Getting Sentimental Over You” was an indirect shot, as Sinatra recorded the song in his early years with the Tommy Dorsey Orchestra.) Up until now, Dylan’s most notable positive engagement with The Voice was a performance at Sinatra’s 80th birthday gala in 1995, where he was the only artist not to present a song associated with the honoree. Dylan closed the show with his own “Restless Farewell”; after finishing, he (touchingly) said, “Happy Birthday, Mr. Frank.”
Twenty years later comes “Shadows in the Night.” In a remarkable interview) he gave to AARP Magazine, Dylan explained how Sinatra got under his skin. He said that the older singer “had this ability to get inside of the song in a sort of a conversational way. Frank sang to you, not at you, like so many pop singers today. Even singers of standards. I never wanted to be a singer that sings at somebody. I’ve always wanted to sing to somebody. I would have gotten that subliminally from Frank many years ago. Hank Williams did that, too. He sang to you.
“I myself never bought any Frank Sinatra records back then, if that’s what you mean. I never listened to Frank as an influence. All I had to go on were records, and they were all over the place, orchestrated in one way or another. Swing music, Count Basie, romantic ballads, jazz bands — it was hard to get a fix on him. But like I say, you’d hear him anyway. You’d hear him in a car or a jukebox. You were conscious of Frank Sinatra no matter what age you were. Certainly nobody worshipped Frank Sinatra in the ’60s like they did in the ’40s. But he never went away. All those other things that we thought were here to stay, they did go away. But he never did.”
Elsewhere in the interview, Dylan says, “Well, a lot of these songs, you know, have been pounded into the ground over the years. I wanted to use songs that everybody knows or thinks they know. I wanted to show them a different side of it and opened up that world in a more unique way. You have to believe what the words are saying and the words are as important as the melody. Unless you believe the song and have lived it, there’s little sense in performing it.”
The key to the success of “Shadows in the Night” — for it is lovely, haunting piece of work — is that Dylan convinces us that he really does believe in the material. He’s accompanied by his regular touring band, with some horns added in now and again, but the only player who really counts is Donny Herron. His pedal steel guitar is a very versatile instrument, giving a high keening sound one minute and, the next, ably filling in for the Gordon Jenkins strings Sinatra turned to so often in his introspective ‘50s.
And Dylan — planted six inches away from the microphone, he tells AARP — sings to us, not at us, as full-throated as he’s been since “Love and Theft” (2001). The lyrics have their moments of triteness, but he mines the lyricism that’s in them as well, which connected listeners over the airwaves so long ago. The two words that come up most often on “Shadows in the Night” — more than kiss (6 times), moon (8) and love (9) — are variants of I (80 times) and you (53). Dylan takes that seriously and makes this record feel like a dialogue from the heart.
It’s an idiosyncratic, imperfect disk, as how could it not be? On “I’m a Fool to Want You” (one of the few Sinatra songs on which he took a co-writing credit) and “Autumn Leaves,” the tempo is so slow it sometimes seems to stop. “Where Are You?,” to these ears, feels a little undernourished. But at some point in all the songs, even the familiar “Some Enchanted Evening,” Dylan tunnels down and finds a heart that’s still beating, strong and true.
Dylan told AARP, “These songs have been written by people who went out of fashion years ago. I’m probably someone who helped put them out of fashion. But what they did is a lost art form. Just like da Vinci and Renoir and van Gogh. Nobody paints like that anymore either. But it can’t be wrong to try.”
Ben Yagoda is a professor of journalism at the University of Delaware and the author, most recently, of The B-Side: The Death of Tin Pan Alley and the Rebirth of the Great American Song.”