Can you understand my pain? Dylan’s worst songs

My picks for worst Dylan songs are failures of imagination, excuses for singing like a minotaur, or okay songs hobbled by contemptible arrangements. I could have added “Chimes of Freedom,” a Kristofferson cover with a terrified children’s choir, or “Dark Eyes” (I can’t better Theon Weber’s description: it’s transparently on Empire Burlesque so that stupid people can think it’s the one good song).

10. “Disease of Conceit” (Oh Mercy).

I don’t mind Dylan’s unexpected stresses; they function like iambic pentameter set to the rhythm of English subtitles. But the piano hook is anemic instead of stately, and he indicts an abstraction which can’t rebut the indictment (“What Good Am I” took care of that two tracks earlier).

9. “To Make You Feel My Love” (Time Out of Mind).

Garth Brooks, Billy Joel, Bryan Ferry are among the artists who have covered a plaint so generic that Garth Brooks, Billy Joel, and Bryan Ferry sing it exactly the same.

8. “When The Night Comes Falling From the Sky” (Empire Burlesque)

The arrangement gallumphing in an effort to persuade the principals that they’re having a good time, this 1985 oddity got more sensitive treatment at the hands of the E Street Band. And Roy Bittan’s piano is put to effective use. I’m all for Dylan and octagonal drums (“Tight Connection to My Heart” is one of his best songs), but he and Arthur Baker sound nauseated; Dylan in fact sings as if in the grips of nausea. The two-note blasts of synth horns, the backup singer echoing every word, not a single space for the song to breathe – all as gauche as Dylan’s earring. Plus, the song ain’t that good anyway (“I can hear your trembling heart beat like a river” is a detestable line, with or without Dylan’s Count Chocula vibrato.

7. “Neighborhood Bully” (Infidels)

Not about himself.

6. “Gotta Serve Somebody” (Slow Train Coming)

Not about God. The gleam of the studio rock arrangement makes it worse (and endless).

5. “Hurricane” (Desire)

I had to stop myself from including half of Desire. Admittedly, the fiddle and bongos catch the ear, but telling a straightforward narrative is hell on Dylan’s singing; it has moments where he is audibly trying to catch up with a verse.

4. “Lenny Bruce” (Shot of Love)


3. “Is Your Love in Vain” (Street-Legal)

Archie Bunker yelling at Edith’s corpse, to the accompaniment of saxophones.

2. “Joey” (Desire)

No reason why this fantasia about a king of the street and child of clay has to be eleven minutes and why the drums sound more garish than Empire Burlesque‘s electrobeats.

1. “Rainy Day Woman #12 and 35” (Blonde on Blonde)

Sure, I hate fun. I like New Orleans funeral brass bands though! Dylan’s other song that stopped short of hitting #1 (guess the other) is worth playing once: at sixteen, thinking, “Oh my god he said STONED!”

23 thoughts on “Can you understand my pain? Dylan’s worst songs

      1. humanizingthevacuum, have you a link to the songs you’ve penned and performed?

        Also,”Chimes of Freedom” is a Bob Dylan song…not a Kris Kristofferson song. “They Killed Him” is the Kristofferson song that Dylan covered.

      2. I think you misunderstood the punctuation. I clearly said indicated TKH is the KK song.

        I don’t need to write songs to write about Dylan. Do you need a brown nose to kiss someone’s ass?

    1. I clicked on the first Dylan piece posted here of late because it was linked on Expecting Rain. It was insufferable. Why I bothered to waste a minute of my life reading this new piece is beyond me. Ah, well! Fool me once…

  1. Should have spent more time coming up with better arguments why he thinks these songs are the worst. A one-sentence argument doesn’t explain much, if anything at all.

    1. You act like somebody who shows up without an invitation to the party, spits on the food, insults the curtains, and makes no attempt to learn the history of the house. Check the archives, dear.

      1. I read through some more of your little lists of critiques. Nothing compelling yet, but you’re welcome.

      2. Nah, I’m just fucking with you. You’ve got some pretty good stuff. Sorry I misjudged you on this list alone. I just clicked on this link through expectingrain and I was unaware of your other pieces.

    1. I’m not sure you and your sheep understand how punctuation works; you must all have commiserated before posting at the same time.

  2. “Chimes of Freedom” is a Bruce Springsteen song.
    “Help Me Make It Through Your Article” is by Kris Kristofferson.

  3. The Archie Bunker/Edith comment for “Is Your Love in Vain?” was spot on and made me chuckle. While Kris Kristofferson is a great songwriter, don’t think he wrote “Chimes of Freedom.”

  4. A great list, Alfred Soto! I hope someone forwards this to Dylan so he can remove these tracks from his albums pronto!!! When will you tackle the worst of Mozart and Gershwin? Music lovers around the world await your judgment! Not to split hairs, but Kris Kristofferson didn’t write “Chimes of Freedom.” It’s said that Dylan wrote that song in the backseat of a car while traveling across America. Kristofferson has written some good and memorable songs, but “Chimes of Freedom” isn’t one of them. Do you like The Byrds’s version of “Chimes of Freedom”?!? Man oh man, that version ROCKS!

    1. Good idea! Please share it with him. He has a better sense of humor than his most pedantic fans like you.

      1. His pendatic fans like me?!? Writing in English does not come easily to you, does it?

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