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The Bob Dylan Songbook

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Welcome to Afterglow, I’m your host, Mark Chilla.

Bob Dylan—folk music darling, rock music provocateur, and Nobel Prize-winning songwriter—has become part of the fabric of American Popular Music. However, the world of jazz has always been a bit slow, if not a little reluctant, to embrace the songs of Bob Dylan. That’s not to say that it hasn’t been done. On this week’s episode, I’ll explore the crossover between Dylan songs and vocal jazz, including covers of his songs by Nina Simone, Kurt Elling, Cassandra Wilson and more.

It’s the Bob Dylan songbook, coming up next on Afterglow.

<music - Nina Simone, "Just Like Tom Thumb's Blues">

Nina Simone in 1969 with the Bob Dylan song “Just Like Tom Thumb’s Blues,” originally from Dylan’s 1965 album Highway 61 Revisited.


Mark Chilla here on Afterglow. On this show, we’re exploring vocal jazz covers of songs by Bob Dylan. 

The jazz world was a bit slow to adapt the songs of Dylan, despite their ubiquity in pop, rock, folk, and even R&B. Right now, we’re hearing the Gene Norman Group from their 1965 album Dylan Jazz, one of the first jazz records ever devoted to Dylan.

Singer Nina Simone was an “early adopter” of the songs of Dylan, recording them in the late 1960s (I’ll play some of those later). But most of the recordings I’ll feature this hour come from the last few decades, as vocal jazz artists have tried to develop a new Great American Songbook, and incorporated these Dylan classics.

One of the first artists to cultivate this “new American Songbook” approach to her repertoire was Cassandra Wilson. Wilson has recorded songs by James Taylor, Neil Young, Van Morrison, and Cyndi Lauper. She’s also recorded a few songs by Bob Dylan, including the song “Lay Lady Lay” from his 1969 country-tinged album Nashville Skyline and this next song.

Here is Cassandra Wilson in 2002 with the Bob Dylan song “Shelter From The Storm,” on Afterglow.

<music - Cassandra Wilson, "Shelter From The Storm">

Cassandra Wilson in 2002 with the Bob Dylan song “Shelter From The Storm.” That comes from her 2002 album Belly of the Sun, and “Shelter From The Storm” was originally from Dylan’s 1975 album Blood On The Tracks.

Today, Blood on the Tracks is almost universally seen by critics as one of his best, featuring some of his classic songs like “Tangled Up In Blue” and “Simple Twist of Fate.” Pound for pound, it might be his best album. It’s no wonder that other artists, including jazz vocalists, have mined Blood on the Tracks for songs to cover.

This next singer, Madeleine Peyroux, also recorded a new interpretation of a Blood On The Tracks song. Here is Peyroux in 2004 with her version of Bob Dylan’s “You’re Gonna Make Me Lonesome When You Go,” on Afterglow.

<music - Madeleine Peyroux, "You’re Gonna Make Me Lonesome When You Go">
<music - Diana Krall, "Simple Twist of Fate">

Two songs originally from Bob Dylan’s 1975 classic album Blood On The Tracks. Just now we heard Diana Krall performing “Simple Twist of Fate” from the 2012 Dylan tribute compilation Chimes of Freedom, a charity record for Amnesty International. Before that, Madeleine Peyroux from her 2004 album Careless Love with Dylan’s “You’re Gonna Make Me Lonesome When You Go.”

Few jazz artists have devoted entire albums to Bob Dylan. There’s the Gene Norman album I mentioned earlier, and a recent album from Indianapolis guitarist Charlie Ballentine. As far as vocal jazz artists go, there are even fewer. But singer and keyboardist Ben Sidran is one. Sidran has lived on the outskirts of jazz and rock for decades, recording with the Steve Miller Band and Boz Skaggs, as well as recording his solo jazz records featuring his gruff Leonard Cohen-esque voice.

His 2009 album Dylan Different features his jazz takes on Dylan songs ranging from 1964 to 1989. Here’s one that dates back to 1966 originally on the album Blonde on Blonde.

This is Ben Sidran with “Rainy Day Women #12 & 35,” on Afterglow.

<music, Ben Sidran, "Rainy Day Women #12 & 35">

Singer and keyboardist Ben Sidran with his version of Bob Dylan’s “Rainy Day Women #12 & 35.” That’s from Sidran’s 2009 all-Dylan album Dylan Different.

Our next Dylan interpreter is jazz singer Abbey Lincoln. For over 50 years, Lincoln had always performed an eclectic mix of socially-conscious jazz standards and original songs. In 1996, Lincoln recorded a version of the 1965 Bob Dylan song “Mr. Tambourine Man” that evokes the style of a beat poetry performance, the kind of stuff that inspired much of Dylan’s early songwriting style.

Here’s Abbey Lincoln in 1996 with Bob Dylan’s “Mr. Tambourine Man,” on Afterglow

<music - Abbey Lincoln, "Mr. Tambourine Man">

From Abbey Lincoln’s 1996 album called Who Used To Dance, that was Lincoln with the Bob Dylan song “Mr. Tambourine Man.”

Coming up after a short break, we’ll hear more vocal jazz covers of songs by Bob Dylan, stay with us.


Production support for Afterglow comes from:

Soma Coffee House and Juice bar, specializing in juices, espressos and Fair Trade Organic Coffee. Serving from downtown at Kirkwood and Grant and on the corner of third and Jordan.  Online at i heart soma dot com

And from Stephen R Miller C P A, in downtown Bloomington at Graham Plaza, offering personal and small business income tax preparation and financial reporting. Helping clients reach financial goals for over thirty years. 8-1-2 - 3-3-2 - 0-5-5-7

I’m Mark Chilla, and you’re listening to Afterglow


Welcome back to Afterglow, I’m Mark Chilla. We’ve been exploring the music of Nobel Prize-winning songwriter Bob Dylan this hour.

<music clip - Bob Dylan, "Day In Day Out">

While Dylan himself has been exploring his jazz roots as of later, recording the classic standards of Frank Sinatra in his own haunting way. But on this show, I’ve been exploring the opposite: jazz singers taking Dylan’s music and lyrics and performing it in their own way.

I’ll turn now to singer Kurt Elling, one of the most emotive contemporary male jazz singers. Elling recorded a Dylan song on his 2018 album The Questions. And like Abbey Lincoln did on the last song we heard, Elling’s performance strips away the folk elements of the music to highlight the beat poetry jazz present in Dylan’s raw lyrics.

Here’s Kurt Elling with Bob Dylan’s 1963 song “A Hard Rain’s Gonna Fall,” on Afterglow.

<music - Kurt Elling, "A Hard Rain’s Gonna Fall">

Kurt Elling, performing a Bob Dylan song from Dylan’s 1963 album The Freewheelin’ Bob Dylan. That comes from Elling’s 2018 album The Questions.

Some Bob Dylan songs lend themselves more to jazz interpretations than others. While Kurt  Elling might have brought out the beat poetry jazz of Dylan’s lyrics, a singer like Curtis Stigers can bring out the light jazz-pop in a Dylan melody. 

The 1967 Dylan song “I’ll Be Your Baby Tonight” from the album John Wesley Harding, in Dylan’s hands, resembles a 1920s Tin Pan Alley song as performed by a 1940s country singer. When Curtis Stigers sings it, he takes that Tin Pan Alley melody and makes it sound like a 1950s Frank Sinatra/Nelson Riddle song.

Here’s that recording now: Curtis Stigers in 2007 with the Bob Dylan song “I’ll Be Your Baby Tonight,” on Afterglow.

<music - Curtis Stigers, "I’ll Be Your Baby Tonight">

Curtis Stigers from his 2007 album Real Emotional performing the 1967 Bob Dylan song “I’ll Be Your Baby Tonight.” Stigers has recorded several other Bob Dylan songs, including 1962’s “Don’t Think Twice It’s Alright” and 1999’s “Things Have Changed.”

Our tribute to the jazz interpretations of Bob Dylan songs is winding down. A few interpretations had to be left off the show due to time, including Jimmy Scott’s 1996 unique interpretation of the Dylan song “When He Returns,” part of Dylan’s Christian phase. And Norah Jones in 2002 recorded a banjo-laden version of that last song “I’ll Be Your Baby Tonight.”

But I want to close off this hour with the jazz singer who was one of the first to realize the creative potential in a Bob Dylan cover: Nina Simone. Simone started performing Dylan’s songs way back in 1966 with her folky cover of “The Ballad of Hollis Brown” and later performed classic Dylan songs like “The Times They Are A-Changin’.”

I’ll close with two other Dylan songs she recorded and completely transformed into her own. To begin, here’s Nina Simone in 1971 performing the Bob Dylan song “Just Like A Woman,” on Afterglow.

<music - Nina Simone, "Just Like A Woman">
<music - Nina Simone, "I Shall Be Released">

Nina Simone with two songs by Bob Dylan. Just now, we heard Dylan’s song “I Shall Be Released,” originally recorded by The Band in 1968. That comes from Simone’s 1969 album To Love Somebody. And before that, Dylan’s 1966 song “Just Like A Woman,” from Simone’s 1971 album Here Comes The Sun.

<music - Chris Thile and Brad Mehldau, "Don't Think Twice It's Alright">

Brad Mehldau and Chris Thile playing some Dylan in the background... and thanks for tuning in to this look at the Bob Dylan Songbook, on Afterglow.



Afterglow is part of the educational mission of Indiana University, and produced by WFIU Public Radio in beautiful Bloomington, Indiana. The executive producer is John Bailey.

Production support for Afterglow comes from:

Soma Coffee House and Juice bar, specializing in juices, espressos and Fair Trade Organic Coffee. Serving from downtown at Kirkwood and Grant and on the corner of third and Jordan.  Online at i heart soma dot com

And from Stephen R Miller C P A, in downtown Bloomington at Graham Plaza, offering personal and small business income tax preparation and financial reporting. Helping clients reach financial goals for over thirty years. 8-1-2 - 3-3-2 - 0-5-5-7

Playlists for this and other Afterglow programs are available on our website. That’s at indianapublicmedia.org/afterglow.

I’m Mark Chilla, and join me next week for our mix of Vocal Jazz and popular song from the Great American Songbook, here on Afterglow

bob dylan

Bob Dylan in 1963 (Wikimedia Commons)

Bob Dylan—folk music darling, rock music provocateur, and Nobel Prize-winning songwriter—has become part of the fabric of American Popular Music. He has reinvented his singing and songwriting style countless times—recently, he’s even become a spooky interpreter of Great American Songbook on recent albums Shadows In The Night, Fallen Angels, and Triplicate.

However, the world of jazz has always been a bit slow, if not a little reluctant, to embrace the songs of Bob Dylan. That’s not to say that it hasn’t been done. On this week’s episode, I’ll explore the crossover between Dylan songs and vocal jazz, including covers of his songs by Nina Simone, Kurt Elling, Cassandra Wilson and more.


Despite their ubiquity in pop, rock, folk and even R&B, Dylan songs were largely rejected by jazz in the 1960s and 1970s. The few exceptions were the Gene Norman Group who devoted their 1965 album Dylan Jazz to light jazz-pop interpretations of Dylan as well as singer Nina Simone.

Simone was an "early adopter" of the songs of Dylan, realizing their creative potential almost immediately. Simone started performing Dylan’s songs way back in 1966 with her folky cover of “The Ballad of Hollis Brown” and later performed classic Dylan songs like “The Times They Are A-Changin’" and "Just Like Tom Thumb's Blues." She recorded Dylan's "Just Like A Woman" on her 1971 album Here Comes The Sun and created a memorable version of "I Shall Be Released" (originally recorded by The Band) on her 1969 album To Love Somebody.

Nina Simone is an exception, however. Most Dylan jazz interpretations come from the last several decades, as vocal jazz artists have tried to develop a "new Great American Songbook" incorporating rock classics by Dylan and others.

One of the first artists to cultivate this “new American Songbook” approach to her repertoire was Cassandra Wilson. Wilson has recorded songs by James Taylor, Neil Young, Van Morrison, and Cyndi Lauper. She’s also recorded a few songs by Bob Dylan, including the song “Lay Lady Lay” (from Dylan's 1969 country-tinged album Nashville Skyline) on her 2003 album Glamoured and "Shelter From The Storm" (from Dylan's 1975 album Blood On The Tracks) from her 2002 album Belly Of The Sun.

Dylan's Blood on the Tracks is almost universally seen by critics today as one of his best, featuring some of his classic songs like “Tangled Up In Blue” and “Simple Twist of Fate.” Pound for pound, it might be his best album. It’s no wonder that other artists, including jazz vocalists, have mined Blood on the Tracks for songs to cover. Madeleine Peyroux recorded the Blood On The Tracks song "You're Gonna Make Me Lonesome When You Go" on her 2004 album Careless Love, and Diana Krall recorded "Simple Twist Of Fate" on the 2012 Dylan tribute compilation Chimes of Freedom, a charity record for Amnesty International.

Few jazz artists have devoted entire albums to Bob Dylan. There’s the Gene Norman album I mentioned earlier and a recent album from Indianapolis guitarist Charlie Ballentine. As far as vocal jazz artists go, there are even fewer. But singer and keyboardist Ben Sidran did so on his 2009 album Dylan Different. Sidran has lived on the outskirts of jazz and rock for decades, recording with the Steve Miller Band and Boz Skaggs, as well as recording his solo jazz records featuring his gruff Leonard Cohen-esque voice. Dylan Different features a variety of Dylan songs ranging from 1966's "Rainy Day Women #12 & 35" to 1989's "Everything is Broken."

Despite being a folk music icon, Dylan's lyrics are drenched in beat poetry, which was a product of the jazz age. So stripped from their folk music roots, a raw Dylan lyrics could slip easily into a wordy beat-poetry jazz interpretation. A few singers have done this, including Abbey Lincoln and Kurt Elling, singers who have embraced the poetic side of jazz. Abbey Lincoln has a great interpretation of Dylan's "Mr. Tambourine Man" one her 1996 album Who Used To Dance. More recently, Elling has created a sprawling performance of "A Hard Rain's Gonna Fall" on his 2018 album The Questions.

Some Bob Dylan songs lend themselves to jazz interpretations more than others. While Kurt Elling might have brought out the beat poetry jazz of Dylan’s lyrics, a singer like Curtis Stigers can bring out the light jazz-pop in a Dylan melody. The 1967 Dylan song “I’ll Be Your Baby Tonight” from the album John Wesley Harding in Dylan’s hands resembles a 1920s Tin Pan Alley song as performed by a 1940s country singer. When Curtis Stigers sings it on the 2007 album Real Emotional, he takes that Tin Pan Alley melody and makes it sound like a 1950s Frank Sinatra/Nelson Riddle song. Stigers has also recorded several other Bob Dylan songs, including 1962’s “Don’t Think Twice It’s Alright” and 1999’s “Things Have Changed.”

Our tribute to the jazz interpretations of Bob Dylan sadly had to leave a few songs off due to time, including Jimmy Scott’s 1996 unique interpretation of the Dylan song “When He Returns” (part of Dylan’s Christian phase), and Norah Jones's 2002 banjo-laden version of that last song “I’ll Be Your Baby Tonight.” But as more jazz artists continue to embrace the songs of Bob Dylan, I'll likely devote a second episode to his music.


You can read more about jazz interpretations of Bob Dylan in the following articles by Tom Wilmeth of Jazz Times ("Jazz In The Key of Bob") and Jim Macine of Lament For A Straight Line ("10 Great Jazz Spins On Bob Dylan").

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