Dylan’s Dozen: The Twelve Greatest Bob Dylan Songs

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-80’s 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.

One thought on “Dylan’s Dozen: The Twelve Greatest Bob Dylan Songs

  • Well, Budokan and Hard Rain are two of my favorites; as is a recently acquired bootleg of the Rolling Thunder tour. I think he has made some amazing live music. That may be the definition of ‘best’ for me.


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