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September 19, 2025 114 mins

With so many dozens of albums over so many wildly disparate eras, it can take a lifetime to truly get your arms around Bob Dylan. On this episode, Kirk is joined by two guests who have spent their lifetimes doing exactly that. Matt Sitman and Sam Adler-Bell, in addition to co-hosting the terrific political history podcast Know Your Enemy, are both lifelong Dylan fans. This spring, they came on the show to give listeners a tour of Dylan's many eras, and to give newcomers a place, or places, they might start getting to know him better.

DYLAN SONGS DISCUSSED, IN RELEASE CHRONOLOGY

  • “Blowin in the Wind”  and “Corrina, Corrina” from Freewheelin’ Bob Dylan, 1963 (and as sung by Peter, Paul and Mary)
  • “Like A Rolling Stone,” “Just Like Tom Thumb’s Blues,” “From a Buick 6” from Highway 61 Revisisted, 1965
  • “Subterranean Homesick Blues,” “Mr. Tambourine Man,” and “Outlaw Blues” from Bringing it All Back Home, 1965
  • “Rainy Day Women #12 & 35” and “Pledging My Time” from Blonde on Blonde, 1966
  • “All Along the Watchtower” and “I’ll Be Your Baby Tonight” from John Wesley Harding, 1967
  • “Lay, Lady, Lay” and “Girl from the North Country” (with Johnny Cash) from Nashville Skyline, 1969
  • “Knockin’ on Heaven’s Door” from Pat Garret & Billy The Kid Original Soundtrack, 1973
  • “Forever Young” from Planet Waves, 1974
  • “Tangled Up in Blue” from Blood On The Tracks, 1975
  • “Hurricane” and “Romance in Durango” from Desire, 1976
  • “Changing of the Guards” from Street-Legal, 1978
  • “Serve Somebody,” and “Do Right to Me Baby (Do Unto Others)” from Slow Train Coming, 1979
  • “Saved” from Saved, 1980
  • “The Groom’s Still Waiting At the Alter” and “Lenny Bruce” from Shot of Love, 1981
  • Pressing On” and "Solid Rock" live in Toronto, 1980
  • “Neighborhood Bully,” “Jokerman,” “Sweetheart Like You” from Infidels, 1983
  • “Dark Eyes” from _Empire Burlesqu_e, 1985
  • “Brownsville Girl” from Knocked Out and Loaded, 1986
  • “Sylvio” from Down In The Groove, 1988
  • “Everything Is Broken” and “Most of the Time” from Oh Mercy, 1989
  • “Hard Times” from Good As I Been to You, 1992
  • Train of Love,” Johnny Cash tribute, 1999
  • “Pay In Blood” from Tempest, 2012
  • “I’m A Fool To Want You“ by Frank Sinatra, Jack Wolf, and Joel Herron from Shadows in the Night, 2015, and as recorded by Frank Sinatra
  • “Polka Dots and Moonbeams” by Jimmy Van Heusen and Johnny Burke, from Fallen Angels, 2016
  • “How Deep is the Ocean” by Irving Berlin from Triplicate, 2017
  • “I’ve Made Up My Mind to Give Myself to You” from Rough and Rowdy Ways, 2020

ALSO DISCUSSED/REFERENCED:

  • The Know Your Enemy episode about Dylan's The Philosophy of Modern Song
  • "Moonlight Mind" by Will Epstein and High Water from Crush, 2016
  • "Lonely Woman" by Ornette Coleman from The Shape of Jazz to Come, 1959
  • "Rainy Day Women #12 & 35" as recorded by Tom Petty and the Heartbreakers
  • Sam’s review of A Complete Unknown in The Nation
  • Bob Dylan: Expecting Rain website
  • Episode one, "Weather”, from Dylan’s radio show Theme Time Radio Hour, featuring Muddy Waters on "Blow Wind, Blow”
  • Audio from D.A. Pennebaker’s 1967 documentary Bob Dylan: Don’t Look Back
  • Audio from Scorses’s 2005 documentary No Direction Home: Bob Dylan

GUEST MUSIC PICKS:

  • Sam: Lucinda Wiliams, Car Wheels on a Gravel Road, 1998
  • Matt: Willie Nelson, Across the Borderline, 1993

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