Dylan’s worst

Bob Dylan is an artist I hugely admire. I always have done. But no artist can be excellent all of the time and a good many of those who have enjoyed a long career have produced much that is average and a fair amount of that which is terrible. William Wordsworth, having written sublime poetry during his first forty or so years, proceed to produce copious indifferent, occasionally dire, verse thereafter. He literally could not help himself. Neither, at times, can Bob.

So now I am going to consider the worst of Bob Dylan. This is not an uncommon exercise. There have been numerous lists and polls labelled as such, in which a few songs recur with some frequency: ‘Joey’, ‘Ballad in Plain D’, ‘Wiggle Wiggle’, in particular. But there is little science behind such selections. Often they are based on prejudice rather than dispassionate consideration – so, for example, a readers’ poll held by Rolling Stone magazine in 2013 came up with songs that, more often than not, are thought of as commendable: ‘Gotta Serve Somebody, ‘Lay L:ady Lay, ‘If Dogs Run Free’, alongside the above-mentioned trio. ‘ Gotta Serve Somebody’ presumably for introducing his generally unwelcome Christian phase; ‘Lady Lady Lay’ for the soupy voice he adopted for his country phase; ‘If Dogs Run Free’ because the readers didn’t like the scat signing of Maeretha Stewart. Truth is, it’s a fine song, creatively imagined, and if you don’t like scat then fair enough, but that doesn’t make it a bad song. Ditto a change of voice or a change of avowed belief.

To assess what is a bad Bob Dylan song, or indeed a bad song from anyone, one needs criteria, which can then be applied objectively to his musical output. I propose these seven:

1. Lyric – Most important with Dylan must be the quality of the words, naturally. So when does his poetic gift fail? It can be laziness (his predilection for list songs – such as ‘Gotta Serve Somebody’), it can be crassness of argument or theme (e.g. ‘The Ugliest Girl in the World’, which also features in the Rolling Stone list), it can be pretentiousness (‘Chimes of Freedom’, anyone?). It can be misuse of his gift for words. In short, it’s where Dylan has come up with the wrong words.

2. Music – A good song is musically inventive; a bad one is devoid of imagination. Tired ideas (all those generic blues retreads); inappropriate musical styles (reggae, almost every time, even if you did have Sly & Robbie play with you); nondescript tunes, particularly if they bring down a fine lyric (‘Crossing the Rubicon’, for example). It’s when the tune is wearisome that the verdict must be harsh.

3. Production – A song can, of course, be made worse through poor production, which is what damns so much of Dylan’s 1980s output when he lost his musical direction and any sensible idea of what sound he wanted, weaknesses that were then accentuated by some woefully inappropriate producers (we must assume, however, that Dylan had some influence over the production, or else the badness is nothing to do with him). Yet a bad production may be the result of a bad song per se – that is, the one inspires the other. However, this can be rectified by…

4. Cover versions or other recordings – The song as originally recorded by Dylan may be poor, but a strong cover version or alternative recording by Dylan may be the song’s salvation – for example, ‘Can You Please Crawl Out Your Window’ was a dreadful mid-60s single from when Dylan was trying too hard to show off, but is saved (just) by a fine cover from Wilko Johnson and Roger Daltrey, and better-judged studio takes on Dylan’s The Cutting Edge ‘bootleg’. We must consider the song not just as Dylan originally recorded it, but as he may be re-recorded it (so ‘When the Night Comes Falling From the Sky’, a shocker on Empire Burlesque, is almost a revelation on the Bootleg Series 1-3), or where others have found virtues in a song that Dylan himself mangled. Also, the sign of a bad song may be the lack of cover versions it has enjoyed (but be wary, for some gems have attracted bafflingly few covers – ‘Never Say Goodbye’, for example).

5. Authorship – The song much be entirely composed by Dylan, thus discounting such painful misjudgements as ‘Joey’ (a tear-jerking paean to mobster Joey Gallo, co-written by Jacques Levy) and ‘The Ugliest Girl in the World’ (Robert Hunter being the collaborator in shame). Equally, bad recordings by Dylan of other people’s songs must be discounted, if we are considering the songwriter rather than the performer. So no ‘Big Yellow Taxi’ or ‘The Boxer’. Dylan must be the only guilty party.

6. Timing – Where a song falls in the artist’s career matters. Simplistically that might be that the older the artist is the wiser he ought to have been by then, but it is more complicated than that. It must to relate to particular creative and/or reputational highs. Bad songs produced at your peak are all the more egregious.

7. Duration – The longer a bad song goes on, the worse it must be. A bad, short song at least does not detain us too long. A long one shows vanity and misjudgement. ‘Sad-Eyed Lady of the Lowlands’, anyone?

With all these considerations in mind, what are the ten worst Bob Dylan songs? Well, of course, one cannot be absolutely scientific if the choice is one’s own and you do not trust to polling. The very nature of badness demands subjectivity, since the result affects us personally. That is, a bad song is a form of insult. And you can’t insult everybody. Most of the time.

Moreover, no one, except a comedian, sets out to write a bad song. Each song that Dylan wrote must, at some point, have seemed like a good idea. The bad ideas were screwed up and thrown into the litter basket at the point of conception. The ones that were kept made it into the studio, were recorded, played over repeatedly, decided upon, released, then sung in concert, each stage an affirmation of belief. Each had a goodness in them.

Yet some songs are objectively bad. They can only exist because the artist forgot themselves. There is a difference here between the artist and the hack. Many bad songs have been written by inferior composers, but the bad song from an esteemed artist has a different kind of quality to it. It tells us that genius is an elusive gift, which anyone who possesses it may lose, and perhaps never regain. Badness reminds us of the frailty of art, and makes us hope for the good. The artist is never entirely in control of their art. There must be fault lines, blemishes, blind spots, where certainty fails and the artist finds themselves alone, staring into the pit. The bad song is an admission of loneliness, and of fear – fear not only on their part but on the part of we who listen. Art is fragile, and so must be our belief.

Anyway, these are my ten choices, in reverse order of dreadfulness. My apologies to anyone who thinks any one of the ten is a misunderstood masterpiece. Your faith does you credit.

10. Clean Cut Kid (1985)

What do you need to have to be bad Dylan song? Let’s review the criteria. Lyric: an utterly obvious account of the ruin of a young man sent off to the Vietnam War (written ten years after the fall of Saigon). Music: wearisome mid-tempo rock. Production: that crashing drumbeat sounds like every Dylan follower banging their head on the floor in agony. Cover versions: one of moderate enterprise, by Carla Olson and the Textones. Authorship: all his own work. Timing: part of an album, Empire Burlesque, that showed the faint rise in quality of Infidels had raised false hopes. Duration: four minutes and fifteen seconds too long.

9. Lay Down Your Weary Tune (1963, released 1985)

Some of Dylan’s worst songs have occurred when he started to believe in his current image. For the most part he has been notable for maintaining an ironic distance between perception and reality . ‘Lay Down Your Tune’, however, is the work of someone fresh from the initial praise he received as a wordsmith, who now thinks he is a poet rather than thinking poetically. It was, according to Dylan, an attempt to capture the substance of a Scottish ballad, but the heavy alliteration pains the ear (“rest yourself ‘neath the strength of strings”) and a stanza like this one is undergraduate twaddle: “The last of leaves fell from the trees / And clung to a new love’s breast / The branches bare like a banjo moan / To the winds that listen the best”. The Byrds had a go at a cover version, which only accentuates the tweeness of the melody.

8. Driftin’ Too Far From Shore (1986)

Probably Dylan’s most reviled album is 1986’s Knocked Out Loaded, in which he entirely lost what songs are for. The record company needed an album so he provided, but had to turn to other writers to help produce enough dirges to fill out 35 minutes of music (and I’m included the annoying ‘Brownsville Girl’, the unnecessary epic co-written with Sam Shepherd, even though some revere it). Because of these collaborations, only two songs qualify under our criteria. ‘Maybe Someday’ would shame anyone, but it at least has a hook of moderate interest. ‘Driftin’ Too Far From Shore’ sounds like everything regrettable that the Eighties gave to popular music, concentrated in the one song. Terrible as the plastic production is, it suits the song. It’s Dylan as Rick Astley.

7. Black Crow Blues (1964)

This clumsy blues number is the weakest on Another Side of Bob Dylan, an album uneven in its ideas but all of them interesting, bar this one. Dylan’s piano playing is rudimentary without charm, the phrasing is completely askew (so words and tune do not work together), and though the last verse has interesting imagery (“Black crows in the meadow / Sleeping across a broad highway), it feels like a song that was quicker to write than it would have been to perform – had Dylan ever performed it live, which (to date) he has not. And for this he left out ‘Mama You’ve Been on Your Mind’ from the album.

6. I Shall Be Free (1963)

Dylan’s early folk period recordings include several shaggy dog/talking blues songs which may have amused audiences at the Café Wha? but have dated badly. Of these, the unlovely, sloppy ‘I Shall Be Free’ makes into this list for its position as the final song on the album that announced Dylan’s genius to the world, The Freewheelin’ Bob Dylan. Just what is this throwaway nonsense doing after ‘Blowin’ in the Wind’, ‘Masters of War’ and ‘Don’t Think Twice It’s All Right’? Dylan has never played it in concert, no one (so far as I can discover) has covered it. It’s a waste of time and language.

5. Had a Dream About You, Baby (1988)

Dylan’s 1980s period, when the muse seemed to have left him, ought to have supplied most of the numbers for this bottom ten, were it not for cover versions that have proven that a degree of songwriting gift remained underneath the crass productions and Dylan’s uneven approach. Certainly listening again to his all of his 80s output – as I bravely did as preparation for writing this post – suggested work overall that was seldom bad, just progressively wearisome to listen to. But ‘Had a Dream About You, Baby’ is just plain awful. It is a generic rocker, the kind that only a tired old man might sing (which makes the lyric somewhat on the creepy side). For anyone else, this would have been a throwaway B-side at best. Because he is Bob Dylan, that must make a bad song worse.

4. Ballad in Plain D (1964)

This notorious number from Dylan’s folk period is rightly damned for its juvenile spite. Even Dylan has said it was a mistake. Over eight excruciating minutes he lays bare the collapse of his relationship with Suze Rotolo and uses the opportunity of an album release to be vindictive about her sister. It’s one long self-pitying whine, devoid of any psychological insight, and precious little musical interest too. It’s a debasement of the folk medium. Remarkably, there’s a half-decent cover version by Michael Chapman. This mustn’t be allowed to save it.

3. Wiggle Wiggle (1990)

OK, were there to be another public poll for Dylan’s worst, ‘Wiggle Wiggle’ would probably win it, ticking every box in doing so. It’s a demeaning throwaway number, one of Dylan’s lazy list songs, a manner to which he reverted repeatedly in the 1980s when he had run out of ideas. His excuse for the song is that it was meant for one of his children, but it’s more leering than nursery: “Wiggle to the front, wiggle to the rear / Wiggle till you wiggle right out of here / Wiggle till it opens, wiggle till it shuts / Wiggle till it bites, wiggle till it cuts”. The fact that it opens the album Under the Red Sky, dashing hopes after the uplift of the previous album Oh Mercy, has made it all the worse. So why isn’t it number one here? Maybe it’s the hint of menace in the words. But no, it’s because the next two plumb even greater depths.

2. T.V. Talking Song (1990)

Under the Red Sky is not all that bad, with two strong songs (‘Born in Time’ and the title number) and only two stinkers – the above-mentioned ‘Wiggle Wiggle” and ‘T.V. Talkin’ Song’. This wretched number sees Dylan witnessing debates at London’s Hyde Park Corner about the evil effects of watching television. Dylan reports the speech of others, but the trite views have to be his, something confirmed by the singularly lame final verse: “The crowd began to riot and they grabbed hold of the man / There was pushing, there was shoving and everybody ran / T.V crew was there to film it, they jumped right over me / Later on that evening, I watched it on T.V”. You don’t say. How ironic. What did you say your name was again? It has the slight virtue of novelty in being a one-chord song (Dylan is a master of the form, as noted in an earlier post), but the song’s dreariness and facile argument make listening to it a singularly dispiriting experience.

1. Lenny Bruce (1981)

‘Lenny Bruce’ stands out among the tracks on Dylan’s three overtly ‘Christian’ albums like a blasphemer in paradise. That might not have been so bad, given Lenny Bruce’s taste for well-targeted offence. But the song is just so wrong in every degree. It is maudlin, laden with shallow observations, and saddled with probably the worst verse in Dylan’s entire career: “Maybe he had some problems / Maybe some things that he couldn’t work out / But he sure was funny, and he sure told the truth / And he knew what he was talkin’ about”. Dylan’s tribute songs seem always to fall flat – his corny paean to John Lennon, ‘Roll on, John’, only just missed this bottom ten. What wants to be deep sentiment comes over as so false. Dylan never made a song that felt so insincere as this one. It’s the most pointless song he has ever recorded.

Just to add to the pain, I have produced a Spotify list of the worst of Dylan. It broadens things out to include some notable howlers that do not fit all of the criteria (e.g. co-compositions). The damnable have to be damned.


  • The full worst ten from the 2013 Rolling Stone list are:

    10. It Must Be Santa
    9. Ballad in Plain D
    8. Ugliest Girl in the World
    7. Lay Lady Lay
    6. If Dogs Run Free
    5. Joey
    4. Man Gave Names to All the Animals
    3. Rainy Day Women # 12 & 35
    2. Gotta Serve Somebody
    1. Wiggle Wiggle

    (This list and that below include co-written songs and one, ‘It Must Be Santa’, not written by Dylan at all)

  • In 2015, USA Today produced a ranked listing of all of Dylan’s studio recordings, plus songs played over 100 times in concert, to that date. The song at number one was ‘Mississippi’ (interesting choice). The bottom ten were:

    350. Man of Peace (Infidels, 1983)
    351. Got My Mind Made Up (Knocked Out Loaded, 1986)
    352. Woogie Boogie (Self Portrait, 1970)
    353. Ugliest Girl In The World (Down in the Groove, 1988)
    354. Big Yellow Taxi (Dylan, 1973)
    355. Driftin’ Too Far From Shore (Knocked Out Loaded, 1986)
    356. Trouble (Shot of Love, 1981)
    357. Like A Rolling Stone (Self Portrait, 1970)
    358. Wiggle Wiggle (Under the Red Sky, 1990)
    359. Rainy Day Women #12 & 35 (Blonde on Blonde, 1966)

    I don’t know. I quite like ‘Woogie Boogie’.


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4 thoughts on “Dylan’s worst

  1. I could actually hear your teeth grinding for the length category, “The longer a bad song goes on, the worse it must be”

    1. I’ve always had it in for ‘Sad-Eyed Lady of the Lowlands’. I have barely any teeth left by the time it’s over.

  2. Hi Luke – another great post with much food for thought.
    Lists, whether ‘best of’, ‘worst of’ or utilising some other qualifier, always attract debate. Your list here includes some songs that I would have chosen too, as well as a couple of surprises. For me, the surprises were ‘Black Crow Blues’ and ‘I Shall Be Free’; whilst I wouldn’t argue for either being classics there are other songs in Bob’s extensive oeuvre that are more worthy of being in his worst ten. But maybe it is nostalgia for when I first heard those songs, at a time when dinosaurs stilled grazed on the banks of the Medway, that fuels my more positive opinion of them.
    I think that there’s a half-decent song buried deep in ‘Lenny Bruce’ but can only agree with your charge of its insincerity in the form his Bobness chose to leave it in. I must go back and give “Under a Red Sky” another chance though…

    1. Hi Robert,

      Thank you Robert. List posts are potboilers really, but always fun to write and fun to disagree with. Maybe I’m a bit harsh on ‘Black Crow Blues’, but I was trying to include some less obvious songs – and it’s one that has always disappointed me. I did struggle with the order of them. For a while ‘Clean-cut Kid’ was going to be bottom of the list, until I came across a decent cover version that showed there was a fair song in there, musically at least. And ‘Lenny Bruce’ is such a failure in every degree (though there are a couple of tolerable covers…). ‘Under the Red Sky’ is worth a revisit, selectively. The title track just featured in Dylan’s concerts with Willie Nelson and others.

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