The Essential Bob Dylan Playlist

Ana Leorne
4 min readMay 26, 2021


Putting together an essential Bob Dylan playlist must be one of the most difficult tasks ever. With a career over half-a-century long, full of extreme highs and shameful lows, and featuring thirty-six studio albums plus countless live cuts and bootlegs, it’s virtually impossible to cover all of his work on a single playlist — even if we’re only looking at his major hits and most influential tracks. So for this playlist I decided to consider only his most acclaimed body of work, which roughly spans from his 1962 debut until the late ’70s, with his Born-Againism marking the end of his greatest era.

Besides from mainly focusing on his first two decades of work, the list includes both his unavoidable (hence, “essential”) hits, as well as tracks I also consider to be seminal, although they are much less hyped and therefore frequently left out of best-ofs and things of that nature.

Although I don’t intend to ignore how good of an album Dylan’s self-titled debut is, it’s with The Freewheelin’ Bob Dylan that we kick off our list: both its seminal opening track ‘Blowin’ In The Wind’, plus the bleak lyrical-nihilism folk ballad ‘A Hard Rain’s A-Gonna Fall’, are fundamental to understand his Gaugainism (where he comes from and where he is going), and the film and TV over(ab)used ‘The Times They Are A-Changin’’ completes this early protest trilogy, just before his transformation from Socially Engaged Dylan to Inner Contemplative Dylan.

If I weren’t trying to be unbiased about it, probably all of Dylan’s 1965 album Bringing It All Back Home would be featured here. This being said, the LP’s revolutionary opener (the first glimpse of Dylan’s forthcoming “Judas!” phase) plus the über-covered ‘Mr Tambourine Man’ (hello Byrds!) are absolute must-listens, although I must stress that the disenchanted ‘It’s Alright Ma (I’m Only Bleeding)’ also deserves a top spot for its vivid imagery, which seems to vaguely derive from the apocalyptical ‘A Hard Rain’s A-Gonna Fall’ as its version 2.0.

Completing Dylan’s Sacred Album Trilogy is Highway 61 Revisited and Blonde On Blonde. There are few album openings in rock as legendary as Bobby Gregg’s single snare drum hit in the beginning of ‘Like A Rolling Stone’; everything else — song and album — flows right out from there, as if a huge levee suddenly opened and the river was finally free. ‘Desolation Row’ is an essential listen in order to understand Dylan’s tradition of stunning album closers (‘It’s All Over Now, Baby Blue’ and ‘Sad-Eyed Lady of the Lowlands’ play a similar role on Bringing It All Back Home and Blonde On Blonde, respectively). As for his 1966 double-LP masterpiece, I decided not to include ‘Just Like A Woman’ — which I obviously find brilliant in every way — due to ‘Visions of Johanna’ never getting the love it duly deserves. Less commercial but perhaps more visual and everlasting, this track is the less-hyped cousin of the Blonde On Blonde single, and along with ‘I Want You’, showcases an emotionally and musically more mature Dylan.

From his post-motorcycle accident phase comes John Wesley Harding’s most famous cut, ‘All Along The Watchtower’, which gets special praise for marking Dylan’s fruitful relationship with pre- Big Pink The Band, along with Nashville Skyline’s ‘Lay Lady Lay’, a track originally written to serve as Midnight Cowboy’s theme song (‘Everybody’s Talkin’’ ended up being chosen due to Dylan’s delay on delivery). From there we jump directly into Pat Garrett & Billy the Kid’s ‘Knocking On Heaven’s Door’, whose inclusion was obviously derived from its timelessness, and Planet Waves’ ‘Forever Young’, a beautiful lullaby written for his son Jesse.

And even if late ’70s Dylan begins to make for less of an essential listen, the mid-decade’s brightest gem is undoubtedly Blood On The Tracks, with the LP’s storytelling opener ‘Tangled Up In Blue representing the album on this list. Finishing Dylan’s golden ’70s period are two tracks from Desire: ‘Hurricane’ and his duet with Emmylou Harris, ‘Oh Sister’. Post pas terrible Born-Againers ‘Gotta Serve Somebody’ and ‘Jokerman’ complete our journey.


  • ‘Blowin’ in the Wind’
  • ‘A Hard Rain’s A-Gonna Fall’
  • ‘The Times They Are A-Changin’’
  • ‘Subterranean Homesick Blues’
  • ‘Mr Tambourine Man’
  • ‘It’s Alright Ma (I’m Only Bleeding)’
  • ‘Like A Rolling Stone’
  • ‘Desolation Row’
  • ‘Visions of Johanna’
  • ‘I Want You’
  • ‘All Along The Watchtower’
  • ‘Lay Lady Lay’
  • ‘Knockin’ On Heaven’s Door’
  • ‘Forever Young’
  • ‘Tangled Up in Blue’
  • ‘Hurricane’
  • ‘Oh Sister’
  • ‘Gotta Serve Somebody’
  • ‘Jokerman’

Originally published at in May 2016.



Ana Leorne

Paris-based trilingual music writer. fingers in other pies include film, psychology, history, politics, social dynamics, gender issues, tarot and astrology.