Bob Dylan’s 10 worst songs

After a recent concert at The London Palladium, Bob Dylan left the stage to a hero’s ovation. At which point the man next to me arose and proclaimed, “That little fella, to me, is proof of God’s existence.” It seemed a fair point at the time, Dylan could certainly be considered some of The Almighty’s better work (if you go in for all that creator stuff), but then God must’ve also created Sunderland, which just goes to show that absolutely nobody is immune to an off day.

Dylan might be one of the finest folks to have ever vagabonded his way around our green and blue home, but there are undoubtedly moments where he has abandoned his infinite wisdom and opted instead to offer badly croaked attacks on decency. Yep, only a fool would say that his discography is squeaky clean.

However, to offer the hero a fig leaf, when he fails, he usually fails in the right way: striving to avoid his sturdy laurels and bring something new to his oeuvre. Even when he seems to fail because he doesn’t seem to give enough of a damn, you almost have to applaud that punk disposition—a disposition that indeed comes from the same place as his trailblazing decision to put noses out of joint and go electric.

Nevertheless, there are some efforts where it proves difficult to offer up either of these excuses. Yes, Dylan may well be one of the greatest artists ever to roam the Earth, but these rare offerings beg to differ. From the awfullest cuts of an awful 1980s to tracks that simply have you questioning your sanity, this is the very worst of Bob Dylan.

Bob Dylan’s 10 worst songs:

‘Lily, Rosemary and the Jack of Hearts’

The main downfall of ‘Lily, Rosemary and the Jack of Hearts’ is simply that it is a blot on the otherwise perfect copybook of Blood on the Tracks—and it all could’ve been avoided if the good Lord had intervened for once in his goddamn supposed infinite existence and taken that screeching, tuneless mouth-organ out of Dylan’s cakehole.

Aside from the harmonica, the track actually has a bopping rhythm that could set Sir Douglas Bader’s toes-a-tapping, but amid a beauteous album, that deathly squawk of sonic obscenity is a senseless attack on the senses. “It’s hard to relate to that,” Dylan once said of the album’s celebratory reaction by the masses, “I mean, people enjoying that kind of pain.” Well, Bob, it’s more enjoyable than you’ll ever know, but for a brief moment, my ears are in more pain than you seem to comprehend too.

‘Highlands’

Time Out of Mind was considered one of Dylan’s many returns to form. With ‘Not Dark Yet’ and the likes, it is easy to see why. But with his newfound songwriting confidence pushing him along, he swung a little too close to the sun and offered up the hubris of ‘Highlands’—a near-17-minute ramble, like a dull drunkard telling you about his recent fictional vacation in Scotland.

Similar to one of those arthouse films about ‘life in general and the human struggle’, there is nothing much to this track except generalisation and the human struggle to get to the end. The arrangement is far too simple to warrant it stretching the duration of an episode of Cheers! without a single laugh thrown in along the maudlin way. All the while, he drawls out the meta tagline of the song itself in the lyric: “I feel like I’m drifting.”

‘Street Rock’ (with Kurtis Blow)

In his 2004 memoir Chronicles, Volume One (still waiting for Two), Dylan recounts his 1989 return to form record, Oh Mercy. Although it was his best record for years he speaks with a touch of lamentation about not being able to provide his friend and producer Daniel Lanois with his utmost spiritually profound music of old like ‘Masters of War’ or ‘Gates of Eden’. He explains that to reach such sagacious summits “you have to get power and dominion over the spirits. I had it once and once was enough.”

Nonetheless, Bob Dylan was not dismayed that such heights could never be achieved again, merely that it would take another artist to reach them. Owing to his studio encounter with Kurtis Blow, he was convinced that it would be a rapper to do it. Blow had familiarised Dylan with “Ice T, Run DMC, Public Enemy and NWA,” and their iconoclastic verses struck a note with the folk star once dubbed ‘The Voice of a Generation’, because these guys “weren’t bullshitting,” they were, “poets who knew what was going on,” and they were the next voices to take the mantle. I only wish Dylan had merely championed and admired rap from afar.

‘Ballad in Plain D’

‘Ballad in Plain D’ might not be a bad song, but it is uncomfortable and unnecessary. He now openly regrets it, telling author Bill Flanagan in 1985: “Oh! Yeah. That one… That one I look back and I say, ‘I must have been a real schmuck to write that.’ I look back at that particular one and say, of all the songs I’ve written, maybe I could have left that alone.”

Documenting a brawl between himself, Suze Rotolo and her sister Carla, the song gets painfully personal but not quite in the same way as his candid lyrics that brought a new sense of introspection to music. Simply put, it’s just plain nasty, and that is a sad reality to listen to on an otherwise beautiful album.

‘TV Talkin’ Song’

This track just seems hollow and sad—a grim reminder of how time strips away our virility. Dylan once penned with sagacious vigour one of the greatest attacks on cynical trolls in history, “While one who sings with his tongue on fire / Gargles in the rat race choir / Bent out of shape from society’s pliers / Cares not to come up any higher / But rather get you down in the hole / That he’s in.” And then in 1990, as if to prove the erosion of time, he simply proclaimed that too much TV is bad for you.

It’s not just the simple philosophy that leaves ‘TV Talkin’ Song’ seeming vapid and lazy either, lines like “Your mind is your temple, keep it beautiful and free / Don’t let an egg get laid in it by something you can’t see,” are as messy as the top shelf of a dwarf’s fridge. Complete with unoriginal but inoffensive boogie riffing, Dylan might lament that TV “drag[s] your brain about” but it’s his own thinking cap that seems partly lobotomised here, perhaps he’d binged a bit too much Coronation Street this time out.

‘Ugliest Girl in the World’

Dylan’s writer’s block got so constricting in the 1980s that the only options were to either enlist David Hasselhoff with a sledgehammer or contract Grateful Dead lyricist Robert Hunter. When it comes to the ‘Ugliest Girl in the World’ the former might have actually been preferable. The song punches down like a bad comic, while the music makes you feel like you’ve been placed in a washing machine on a 4-hour one-paced cycle.

You can’t be at the top forever, and Dylan was far from the only one dethroned by the pitfall of the ‘80s. The times were so gaudy that the question was do you say ‘you go your way, and I’ll go mine’ or join them on the technological picket line, a disillusioned Dylan chose the latter in trying times and offered up his worst work as a result.

‘Man Gave Name to All the Animals’

A part of you wants to say that this isn’t bad, that it has its charms, and if you take it as a sort of child-friendly parable then it succeeds. However, if this song didn’t carry Dylan’s name, and an excitable acquaintance raced around your house and proclaimed, ‘I’ve got this great new record to play you!’ If you were a good friend, then the kind thing to do would be to have them sectioned. 

Thankfully it’s quirky enough to be considered a light-hearted respite for Dylan at a time when he was finding Christ, but there is also something oddly grating about the mumbled melody. In short, it’s simply not performed very well. John Lennon might have been in a condemnable vain when he scathingly attacked Slow Train Coming, but his critique that “the singing’s really pathetic” is fair game here. If you’re spreading God’s message, then I’m sure he’d appreciate you annunciating Bob. 

‘Neighbourhood Bully’

If this riff was an item of clothing, it would be those pale blue boot-cut jeans that look like two rolls of carpet. As uncool as an ‘80s beer commercial, this daft and repetitive insult to his legacy is cringy enough to snap a weak jaw. And it just won’t shift, it goes on and on in this tedious ’50-year-old cutting loose in a second-hand convertible’ fashion for nearly five unnecessary minutes. 

All the while, Dylan does his best impression of Dylanesque vocals and the whole thing seems like an exercise in fitting the most cliches into a rock song as is humanly possible. It’s as though he has been inspired by a bad Bob Dylan cover band trying an out ‘an original number’ in a social club. Perhaps oddest of all is that Infidels actually does contain some great moments, so the question marks over this odious effort are all the more puzzling. 

‘Emotionally Yours’

As soon as the gaudy album artwork of Empire Burlesque was released, an air of discombobulating despair hung over the whole enterprise. Dylan emerged from his rather crass-looking Born-Again era cover art into the garish light of sickly photoshop design. The cover is hell enough to make the Pope turn atheist on the off chance that his religiosity might condemn him to a lifetime with the creator of this defecation on the face of decency. 

Why is the awful artwork getting so much attention when it’s the song we’re focussing on? Well, ‘Emotionally Yours’ is the musical manifestation of the ungodliness of the sleeve—it embodies everything that was wrong about the worst side of the tacky ‘80s. If the cover offered up roughly the same level of assurance for the quality of music therein as a Prince Andrew interview, then this song was the guilty plea that he had lost his ways and was happy to offer up a pointless bit of radio-friendly nothingness. 

‘Wiggle Wiggle’

Was this song a joke? Was this some sort of elaborate PR stunt that illuminated the brilliance of his back catalogue by providing a point of such sheer contrast that there is no way to judge it other than with extreme bewilderment, dash it from the mind, and reappraise the magnificence of his past? Did Dylan perceive that his stock had fallen so far that the criticism now seemed outsized when scaled up to his former greatness, so like a disgruntled employee, he clocked in and began a day of sabotage to prove that his previous efforts really did warrant a pay rise? None of this is knowable, but it is so bad that it proves mysterious… and that is by no means a redeeming factor for this act of self-Chernobyling.

Even when the tracklisting for his 1990 Under the Red Sky record was announced, a song by the name of ‘Wiggle Wiggle’ surely stood out as something that should never be uttered from the caustic mouth of the voice of a thousand generations. The track resides to this day as an unexplainable oddity that should’ve been shot at birth if only to spare the world from the head-scratching that has followed. 

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