Dylan’s Dozen: The Twelve Greatest Bob Dylan Songs

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No matter what music I listen to, Bob Dylan always makes the playlist. My ex-wife Cindy and I were drawn together in the mid-80s by a love of Bob, and it may even be that attraction that kept our marriage alive for a dozen years. I do know lists of favorite Dylan songs are a great way to start a heated conversation—almost never for what made the top dozen—always for what was left off.

“But you don’t have anything AT ALL from Blonde on Blonde, Bringing It All Back Home or Highway 61 Revisited!”

“No ‘Blowing in the Wind,’ ‘It Ain’t Me, Babe’ or ‘Rainy Day Women #12 & 35’? UNACCEPTABLE.”

“’Idiot Wind’ or ‘Like a Rolling Stone’ or ‘All Along the Watchtower’ (or insert any of another half-dozen titles) is the best song ever written! How can it not be on your list?”

Knowing I’m going to anger three-quarters of the Dylan fans who read this, these songs make up the heart of the canon. They are the 12 Greatest Bob Dylan songs, properly sequenced for an album, a list for which I will brook no argument.

Bob’s Greatest Songs

  • Baby Let Me Follow You Down
  • Don’t Fall Apart on Me Tonight
  • Brownsville Girl
  • Going Going Gone
  • If You See Her, Say Hello
  • Caribbean Wind
  • Trouble in Mind
  • Lily, Rosemary and the Jack of Hearts
  • Sweetheart Like You
  • Baby Stop Crying
  • Most of the Time
  • Changing of the Guard

For extra credit, please begin arguing over which version of each song should represent it. To stir things up, I’ll say “Going Going Gone” was best played in Budokan.

And to calm things down, I’ll say I could easily choose a different dozen by Saturday, and feel just as strongly about them. Anything can be fired from a canon.


Keith Howard used to be a homeless drunk veteran. Then he got sober and, eventually, became director of Liberty House in Manchester, a housing program for formerly homeless veterans. There, he had a number of well-publicized experiences – walking away from federal funds in order to keep Liberty House clean and sober, a contretemps with a presidential candidate and a $100,000 donation, a year spent living in a converted cargo trailer in Raymond. Today, he lives in a six-by 12-foot trailer in Pittsburg, NH, a few miles from the Canadian border with his dog, Sam. There, Howard maintains tinywhitebox.com, his website, works on a memoir, and a couple of novels while plotting the next phase of his improbable life.