Bob Dylan Does Sinatra and It’s Actually Good
Is this the strangest tribute album of all time? Dylan singing relatively obscure Sinatra songs over a pedal steel back-up? Weirdest of all? It’s pretty compelling.
“Rock and roll smells phony and false,” Frank Sinatra told music fans back during the Age of Elvis. “It is sung, played, and written for the most part by cretinous goons and … is the most brutal, ugly, desperate, vicious form of expression it has been my misfortune to hear.”
Okay, but what do you really think, Frank?
Sinatra softened his stance somewhat in later years, and even recorded an occasional soft rock hit. But could you ever imagine Sinatra releasing an album of Bob Dylan songs? I can’t.
Then again, I would never have imagined Bob Dylan recording an album of Frank Sinatra songs. But here it is, Shadows in the Night, playing in the background while I write. Somehow Highway 61 manages to intersect the Vegas Strip, and oddly enough the music works—but hardly in the way you might expect.
In all fairness, I must note that Bob Dylan and Frank Sinatra had a cordial relationship. Dylan showed up for the Chairman of the Board’s 80th birthday celebration in 1995, and was even a dinner guest at Sinatra’s Beverly Hills home. Even so, these two artists seem to inhabit different musical universes—Dylan still has street cred as a rebellious hero of the heartland, while Sinatra was custom built for the casino penthouse. They could never change places without becoming phony and inauthentic.
But Bob Dylan makes no concessions to the lounge lizards at Caesars Palace on this album. There is nothing slick or contrived about this music. I know that Dylan fans continually fret about him selling out. They were worried about this when he switched to electric guitar at the Newport Festival 50 years ago, and they still get nervous every time he licenses a song to Apple, Pepsi, Google or some other bastion of the capitalist economy.
Trust me, this album is no sell-out.
The first thing you will notice is how Dylan scrupulously avoids all of Sinatra’s signature songs on this supposed tribute album. If you’re wondering how Bob Dylan interprets “New York, New York,” you are out of luck. It’s not here. Nor is “Strangers in the Night” (despite the allusion in the album’s title), or “Fly Me to the Moon” or “My Kind of Town” or “All the Way” or “Night and Day” or “It Was a Very Good Year.” Even “My Way,” a song custom-made for rock-n-rollers and protest singers, is noticeably absent.
Instead we get “That Lucky Old Sun,” a song that is actually more closely linked to Frankie Laine than Frank Sinatra. “Full Moon and Empty Arms,” a Sergei Rachmaninoff adaptation featured here, was a hit for Ray Noble but only a minor success for Sinatra back in 1946. And Dylan covers “Stay With Me,” a forgotten song with a vaguely religious sensibility from the 1963 film The Cardinal. Face it, you can hardly get much further from the casino penthouse than this.
A few of the songs are better known (“Autumn Leaves,” “Some Enchanted Evening”), but are hardly tunes owned by Sinatra. In short, Dylan makes no effort to capitalize on the familiar fare that usually shows up on these kinds of projects. In fact, I’ve never encountered a tribute album that worked harder to avoid songs linked to the artist being honored.
But even more surprising—and this is the big shocker here—is how Dylan adapts these compositions. No, Dylan doesn’t try to sing jazz; and for that, I’m grateful. But he also avoids any hint of rock ‘n’ roll, or his own folk-pop roots. Believe it or not, Shadows in the Night most closely resembles a country album!
The musical accompaniment here is dominated by the twanging sounds of pedal steel guitar. Nelson Riddle would not approve! And Dylan captures a lonesome cowboy tone to his vocal delivery, plaintive and introspective. I almost expected him to break out into a yodel at various junctures in these performances.
Let me blunt: if you are looking for a comparison here, forget anything in the Dylan or Sinatra catalog and recall Willie Nelson’s stylized approach to singing the jazz standards on his Stardust album from 1978. Or imagine how Hank Williams or Patsy Cline might have handled a Sinatra tune. That’s the ambiance you will encounter on Shadows in the Night.
Yet, despite all the incongruities, this album succeeds—but does so on its own terms. The performances are almost painfully heartfelt and direct. Recall that Bob Dylan’s biggest-selling hit singles include very few love songs. In fact, when he did sing about relationships during his youth, Dylan was better at soliciting sex (“Lay Lady Lay”) or breaking up (“Don't Think Twice, It's All Right”). He was the least lovey-dovey of the singer-songwriters of his day. But now, under the guise (perhaps a disguise?) of a supposed tribute album, Dylan exposes a raw emotional vulnerability that jumps out at the listener.
You can’t do this stuff with Auto-Tune. Dylan stretches the notes, sometimes even beyond the breaking point. When he attempts a song with frequent interval leaps, such as Irving Berlin’s “What’ll I Do,” I fear that each phrase will fall off the tightrope and plunge to the ground below. But I wouldn’t change a single note here, not even the ones that would have made Sinatra cringe. The music is actually enhanced by Dylan’s willingness to move outside his comfort zone. Isn’t that what we want from our boldest creative spirits?
No, I don’t think this has anything to do with Frank Sinatra. Dylan is simply tapping into his own emotional depths, and enriching his personal musical legacy. The casino lounge lizards will be disappointed. Rat Pack fanatics will look elsewhere for bachelor pad mood music. Mafia bosses won’t give this album a second listen. But I will—in fact, I already have, and I am going to cue it up again—and you should, too.