The one singer Bob Dylan thought was in a league of her own: “Head and shoulders above most”

Posted On December 21, 2025December 21, 2025

There was never an artist that Bob Dylan wasn’t willing to take on.

The legendary singer-songwriter has an equally legendary list of covers that get filtered through his unique sound. Everyone from The Impressions to the Grateful Dead have been covered by Dylan at some point in his six-decade-long career. But if there was one artist who Dylan always had a soft spot for, it was Frank Sinatra. 

“People talk about Frank all the time — and they should talk about Frank — but he had the greatest arrangers,” Dylan told AARP in 2015. “And not only that, but he brought out the best in these guys. Billy May and Nelson Riddle or Gordon Jenkins. Whoever they were. They worked for him in a different kind of way than they worked for other people. They gave him arrangements that are just sublime on every level. And he, of course, could match that because he 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,” Dylan opinioned. “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.”

“You know, when you start doing these songs, Frank’s got to be on your mind. Because he is the mountain,” Dylan said about covering songs Sinatra made famous on the album Shadows in the Night. “That’s the mountain you have to climb even if you only get part of the way there. And it’s hard to find a song he did not do. He’d be the guy you got to check with.”

“I particularly like Nancy, too! I think Nancy is head and shoulders above most of these girl singers today. She’s so soulful also in a conversational way,” Dylan added.

“And where’d she get that? Well, she’s Frank’s daughter, right? Just naturally. Frank Jr can sing, too. Just the same way, if you want to do a Woody Guthrie song, you have to go past Bruce Springsteen and get to Jack Elliott. Eventually, you’ll get to Woody, but it might be a long process.”

Sinatra would be a constant presence in Dylan’s later career. Dylan explicitly discussed Sinatra in his book The Philosophy of Modern Song and continued to incorporate Sinatra’s influence into his own evolving vocal style. Dylan is more of a crooner than ever these days, and Sinatra is likely the one to credit above all others.

Who else does Bob Dylan consider a favourite singer?

In truth, Dylan has regularly called a run of different singers his favourite. Woody Guthrie, Karen Dalton and many others have been called the pinnacle by Dylan. In a 1978 interview with Rolling Stone, Dylan chirped up in a mostly unrelated conversation, saying, “For some reason, I’ve just thought of my favourite singer.” Prompted by the interviewer, he elaborated, “Uum Kulthum. The Egyptian woman who died a few years ago. She was my favourite.”

But like all true music fans, Dylan’s tastes change. But while he might have different music for different moods, it’s clear that he found something about Nancy Sinatra to be of a completely different level to the rest of female singing set.

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