Dylan’s Dark Journey

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Bob Dylan’s 2015 album Shadows In The Night (Columbia) contains songs that were previously recorded by Frank Sinatra.

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As a young man, Bob Dylan started composing idiosyncratic material because he couldn’t find traditional folk songs that conveyed what he wanted to express. Now, as an old man, he has turned to the Great American Songbook to communicate his feelings, interpreting tunes such as “Autumn Leaves,” “Where Are You?” and Irving Berlin’s masterpiece “What’ll I Do.” One might associate such compositions with a certain degree of theatricality—as opposed to the ostensibly autobiographical, “authentic” songcraft that rockers claim as currency.

Rather than hide behind layers of sonic trickery, Dylan, 73, leaves himself exposed on Shadows In The Night. When a singer sails into senior citizen status, it’s common for a producer to augment his fading instrument with the bulwark of lush orchestration, backing vocalists or sprightly duet partners. Dylan eschews all that. Teamed with his road band, he recorded relatively spare versions of 10 songs—all of which had been previously cut by Frank Sinatra—and then produced the album himself (under the pseudonym Jack Frost).

Whereas Sinatra majestically belted out the prayer “Stay With Me” bolstered by soaring strings, Dylan pairs his gritty vocals with Tony Garnier’s poignant arco work and Donny Herron’s masterfully hypnotic pedal steel guitar.

No one’s ever going to confuse Dylan with Pavarotti, but he’s in fine voice here—at least compared to the growling, guttural delivery on his 2012 album Tempest. The frayed quality of his vocals reinforces the vulnerability and loneliness that his despairing narrators experience.

On “Why Try To Change Me Now,” Herron crafts a dreamy, drifting melodic line as Dylan convincingly portrays a bewildered, weary character who knows that he’ll always be out of step with society’s conventions. Bravo.

(Note: To read a story about recording engineer Al Schmitt—who worked on Shadows In The Night—and his role as a mentor at the 2016 Grammy Camp Jazz Session, click here.)

—Bobby Reed



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November 2025
Gary Bartz
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