Brow Beat

On His New Album of Sinatra Covers, Bob Dylan Pays Tribute to an Era He Once Derided

Bob Dylan performing in 2011.


In his memoir, Chronicles: Volume One, Bob Dylan wrote, “Things were pretty sleepy on the American music scene in the late ’50s and early ’60s. Popular radio was sort of at a standstill and filled with empty pleasantries.” In an interview a few years earlier, he was a bit more 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?

Those comments are just one reason why the contents of Dylan’s new record, Shadows in the Night (to be released Feb. 3), are surprising. The disc might appear to be just another entry, following Linda Ronstadt, Rod Stewart, and many others, in the long-established genre of an aging rocker putting out an album of standards from the Great American Songbook. But Dylan always does things his own way, and his songbook has none of the George Gershwin or Cole Porter chestnuts one might expect. It’s made up, instead, of 10 torch songs and ballads, many of them in a minor key, most of them rather obscure, and all of them recorded, at least once, by Frank Sinatra. And that’s the second surprising thing about the record. It was Dylan, along with the Beatles, who turned the Sinatra performance model—a singer interpreting songs written by other people—on its head.

Most of the tunes on Shadows in the Night (a reference to “Strangers in the Night,” the 1966 record that marked Sinatra’s definitive passage from cool to cheesy, just as Dylan was reaching his ascendance) come from an era of popular music that’s long been derided, and not only by Dylan. After World War II, a two-and-a-half decade torrent of great popular songs by Gershwin, Porter, Jerome Kern, Irving Berlin, Richard Rodgers, and a few dozen other luminaries slowed to a trickle. They were replaced by pseudo-country songs like “Riders in the Sky,” novelty numbers like Patti Page’s “The Doggie in the Window,” and sentimental laments like one of the songs Dylan referred to in his interview, Doris Day’s “If I Give My Heart to You.” (The other, “I’m Getting Sentimental Over You,” was a staple of Sinatra’s early performances with the Tommy Dorsey Orchestra.) In 1948, Variety called the current crop of songs “tripe,” and Sinatra told an interviewer: “I’ve been looking for wonderful pieces of music in the popular vein, what they call Tin Pan Alley songs. You can not find any. Outside of production material, show tunes, you can’t find a thing … ”

The one show tune on Shadows in the Night is “Some Enchanted Evening.” Sinatra’s 1949 record of the South Pacific song reached the Billboard top 10, though it didn’t do as well as versions by Bing Crosby, Perry Como, or Jo Stafford. Some of the rest of the lineup will be familiar only to hardcore Sinatra fans. The opening number, according to the sequence listed on Dylan’s website, is “I’m a Fool to Want You,” one of a handful of songs on which Sinatra indeed has a songwriting credit. He initially recorded it in 1951, while in the throes of his tortured and ultimately doomed relationship with Ava Gardner; the self-flagellating (“Take me back, I love you/ Pity me, I need you”), minor-key soliloquy is commonly viewed as directly reflecting the affair. (Rather amazingly, the B-side of “I’m a Fool to Want You” was the hokiest record of Sinatra’s career, much more so than “Strangers in the Night”—“Mama Will Bark,” on which he teamed up with the TV personality Dagmar and Donald Bain, who provided dog imitations.)

It’s unlikely that Dylan became acquainted with “I’m a Fool to Want You” from the 1951 single. For one thing, he was 10 years old when it came out, hardly an age to respond to a cri de coeur about a doomed love affair. For another, Sinatra included a version of the song on a 1957 LP, Where Are You. This was one of a series of Capitol albums that constituted the most sublime expressions of loneliness and melancholy in 1950s America, and it could be expected to have made an impression on 16-year-old Bobby Zimmerman. The other Where Are You tunes on Shadows in the Night are “The Night We Called It a Day,” a Matt Dennis-Tom Adair ballad Sinatra had originally recorded with Tommy Dorsey in 1942; “Where Are You?”, a 1937 standard by Jimmy McHugh and Harold Adamson; and “Autumn Leaves,” a French pop song given English lyrics by Johnny Mercer in 1947.

Two of the other songs on Dylan’s CD can be found on No One Cares and All Alone, Sinatra’s equally introspective follow-ups to Where Are You. They are lovely and simple ballads: Berlin’s “What’ll I Do,” from 1923, and “Why Try to Change Me Now,” an early composition by Cy Coleman (1929-2004), who was probably the last songwriter to fruitfully ply the tradition that Berlin started. (Fiona Apple has a knockout version of “Why Try to Change Me Now” on a Coleman tribute album, The Best Is Yet to Come.)

The final three cuts on Shadows in the Night are novelties—not novelty numbers, like “Mama Will Bark,” but truly obscure Sinatra releases. The best known is “That Lucky Old Sun,” a sort of ersatz folk anthem, in the mold of “Ol’ Man River”—but it’s well known mainly because of Frankie Laine’s chart-topper, the second best-selling record of 1949. Sinatra’s version peaked at No. 14.

Then there’s “Stay With Me,” the theme from the 1963 film The Cardinal, which Sinatra put on a compilation album two years later. The singer delivers the unapologetically religious lyrics (“I find to my wonder every path leads to Thee,/ All that I can do is pray, stay with me”) with affecting sincerity. On his autumn U.S. concert tour, Dylan—no stranger to matters of faith—used “Stay With Me” as an encore number. YouTube clips show him eschewing the barking deviations he customarily favors in live performance and taking the song completely straight; while taking his bow at a Beacon Theatre show, he appears to wipe away a tear.

Finally, “Full Moon and Empty Arms” is a theme from Rachmaninoff’s Piano Concerto No. 2 that a couple of Tin Pan Alley tunesmiths put words to in 1945. Sinatra’s recording, released the following year, topped out at No. 17. In May, Dylan put the song on his website—presumably the same version that will be on Shadows in the Night. Once more, it’s straightforward and affecting, with Sinatra’s strings replaced by a plaintive pedal steel. And Dylan gives himself over, in full voice, to lyrics like “The moon is there/ For us to share,” which make “I’m getting sentimental over you” look like Keats.

In a statement on his website, Dylan said, “I don’t see myself as covering these songs in any way. They’ve been covered enough. Buried, as a matter a fact. What me and my band are basically doing is uncovering them. Lifting them out of the grave and bringing them into the light of day.” The statement doesn’t mention Sinatra, but “uncovering” is an excellent metaphor for what he and such other superb interpreters as Mabel Mercer, Ella Fitzgerald, and Tony Bennett spent their whole careers doing. (In Bennett’s case, he’s still doing it.) Welcome to the club, Bob.