Dylan and Sinatra: Strangers in the Night 

By Moina Arcee, Mar 30, 2015, edited August 28 2018

Shadows In The Night

Bob Dylan and Frank Sinatra turned their respective musical worlds upside down. In the 1940’s Sinatra had screaming bobby soxers and hit records. In the 1960’s Dylan had a passionate counter cultural fan base and international attention. Both artists were prolific, issuing hit songs and albums in steady streams for decades.

Young geniuses

Musically the two men are as far apart from each other as the decades that separated their emergencies. Dylan and his generation set out to render Sinatra’s music an afterthought, and succeeded. In the twilight of his career, however, Bob Dylan has gone back in time to open the “Great American Songbook,” covering songs by the “old masters”, including Frank Sinatra.

And wouldn’t you know it? It turns out the two men had a relationship – of sorts. Back in 1995 there was a TV special “Sinatra: 80 Years My Way.” Sinatra invited Dylan to participate, and Dylan came out of hiding to attend. The star studded lineup sang various Sinatra songs in tribute. Then Sinatra surprised everyone by asking Dylan to sing one of his songs for Frank. Specifically, Sinatra asked Dylan to sing “Restless Farewell.” Dylan was the only artist to sing his own song on the special. After the song Sinatra gave Dylan a standing ovation. When Sinatra died a few years later, Dylan attended the funeral.

later years

Sinatra was considered a “crooner”, a designation of honor. He sang with exquisite phrasing, his delivery smooth and so easy it seemed he was singing right to you. American music critic Robert Christgau called Frank Sinatra “the greatest singer of the 20th century.”

Dylan, on the other hand, is considered one of the worst singers of the twentieth century. He burst upon the music scene in the 1960’s with an urgent nasal honking, and stomped around for decades with a singing voice David Bowie once described as “sand and glue.” Dylan was an angry prophet, not a crooner like Sinatra, who turned fifty in 1965. Frank sang to his audience; Dylan shouted at his.

Dylan smoked a lot too, which over time wears out the vocal cords. Even more telling is that Dylan has been singing virtually non stop for over fifty years, on his venerable (and really, quite remarkable) “Never Ending Tour.” Over the years, however, Dylan developed a more melodic delivery, and his raspy voice could reach poignancy when singing songs of heartache and loss.

bob dylan

Even so, Dylan’s recent singing voice has been described as “a shredded mess of unintended glottal stops.” Dylan never had a wide singing range, and in later years his range has closed down more. No more high notes for Bobby. As a doctor put it, “The top part of Dylan’s pitch range has dropped, so he can’t access that. When he’s trying to go up in his pitch with certain words and phrases, the voice gets rough. The other thing is that his whole tone is lower.”

All of which makes it logical for Dylan to seek refuge in the “Great American Songbook.” But it is not Dylan’s first exposure. A scruffy looking Jewish boy named Robert Zimmerman, growing up famously out of place among the Scandinavians working the Iron Range in Hibbing, Minnesota, grew up listening to Frank Sinatra, Hoagy Carmichael, Cole Porter, and other American composers in the pantheon.

Then Dylan hopped on southbound Highway 61 and set out to replace the American Songbook with his own. It is telling that the demarcation between composers in the American Songbook and artists of modern music is about 1960. In addition to Dylan and the musical explosion of rock and pop in the sixties, there was also the British Invasion. Musically and lyrically the landscape totally changed.

Those times, they just keep on changing. One thing that hasn’t changed is that Bob Dylan is still touring and releasing albums. His latest is “Shadows in the Night,” a compilation of Sinatra songs. Musically, Dylan takes a minimalist approach: steel guitar, bass, a modicum of horns, understated percussion, all performed by his road band (who surely deserve a medal or something).


The songs are performed respectfully. You can almost feel Dylan making himself comfortable inside a particular standard, for instance, “Some Enchanted Evening,” and then making the song his own. Other highlights are “Autumn Leaves,” and especially “Stay With Me,” which he turns into a prayer. No nasal honking here. Dylan sings in a comfortable register without a sense of urgency, which fits the songs just fine.

Bob Dylan has assumed numerous personas over his fifty year career. His most recent “crooner persona,” if it can be called that, will not be the last musical cloak the restless soul will don. Yet “Shadows in the Night” is a well performed change of pace that is certainly worth a listen.


‘Shadows In The Night’: Dylan Does Sinatra. Really?, by Seth Rogovoy, The ARTery


AARP  The Magazine, EXCLUSIVE: Bob Dylan: The Uncut Interview

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