More about: Bob Dylan11 underrated

Utter the name Dylan around music fans and your bound to encounter these two ways of thinking; he’s the god of pop-literature and one of the greatest of all time, or that he can’t sing and all of his songs are done better by other people.

I hesitate to use the term “marmite” but not many mainstream acts of the last 60 years have divided like Dylan. But with a catalogue as vast as his (the man has 39 studio albums under his belt!) and with a penchant for self-reinvention and shape-shiftery, it must surely be that there’s a Bob tune out there for everyone, somewhere.

It would be all too easy to jump straight to Highway 61 Revisited, Blood on The Tracks or Time Out of Mind, so here are 11 of Bob Dylan’s best deep cuts…

'The Ballad of Hollis Brown' - The Times They Are A- Changin’ (1964)

Potentially his darkest song, this is a grisly tale of a Depression-era South Dakota farmer’s last stand as he’s swallowed into a spiral of poverty and mental illness. The way Dylan cleverly plays with perspective, putting the listener in the shoes of Brown as well as telling you the tale, makes his tortured descent all the more chilling. Heavy listening but well worth your attention.  

'If Not For You' – The Bootleg Series 1-3 (1991)

From perhaps his darkest moment, to one of his most gentle. “If Not For You” opens 1970’s New Morning and is a perfectly serviceable piece of country pop. The version that appears on The Bootleg Series 1-3 however, features a slower pace, with George Harrison adding some gorgeous slide guitar making it a perfect, hazy summer dream of a song. Hearing Dylan asking Harrison if he’s ready to come in on the intro is guaranteed to raise a smile and melt hearts.

'Dark Eyes' – Empire Burlesque (1985)  

They say never to judge a book by its cover, which I usually subscribe to, unless the cover in question is Empire Burlesque. So painfully 80s it invites the listener in with caution, the warning is somewhat necessary as you won’t much of Bob’s best work here. But closer 'Dark Eyes' is one welcome exception which ditches the glossy pop direction of the rest of the tracklist and returns Dylan to his natural state: guitar, harmonica and a great combination of lyrics and melody that remind us never to write him off completely, even in his most questionable moments.

'Moonshiner' - The Bootleg Series 1-3 (1991) 

It’s a common misconception that Bob Dylan can’t sing. Firstly, between his Nashville country croon, Amphetamine fuelled wheeze and post-2000s gruff warble to name a few; it’s not easy to pin down Dylan’s voice. Secondly, one only needs to listen to his rendition of traditional folk tune 'Moonshiner' to know Bob has the capacity to step up vocally, drawing out notes flawlessly with a contemplative melancholy, sounding way beyond his years with a total timelessness.

'The Changing of The Guards' – Street Legal (1978)

In the mid-late 70s period which saw Dylan release Blood on The Tracks and Desire, embark on the Rolling Thunder Revue tour and then take a U-turn towards Christianity, you could be forgiven for forgetting about Street Legal. It’s maybe overlooked too for also not being a classic either frankly, but it has its highlights. Especially this track, with Bob clearly tuned into the pop-rock of the moment, drawing on Springsteen and Tom Petty by making use of blaring saxophones, female backing vocalists and an earworm vocal melody that makes its 6-minute run time fly by. 

'Mama, You been On My Mind' – The Bootleg Series (1991)

With notable covers from Joan Baez to Jeff Buckley as well as Dylan himself having performed it over 200 times, it might not be his most obscure cut, but it earns a place here for highlighting a perplexing recurrence in his discography; brilliant songs baffling being left off albums. This one taking 27 years to appear on an official release is shocking considering its quality. A delicate and vulnerable admission of love which see’s Bob at his most boyish, at one stage even decrying “where you been don’t bother me or bring me down with sorrow, it don’t even matter who you’ll be waking with tomorrow, Mama, you're just on my mind.” Oh Bobby.

'Oxford Town' – The Freewheelin’ Bob Dylan ­(1963)

Despite coming in at just under two minutes, this neat ditty manages to compete with Freewheelin’s big hitters 'Blowin’ in The Wind' and 'A Hard Rain’s A Gonna Fall' in tackling sixties social issues with charm and finesse. Its old school folk melody gives the song a timeless feel, which sadly also extends to its lyrics dealing with racial inequality. It’s message still sounds pertinent today, something Dylan reflected on long after release, saying “I could have written that yesterday, it’s still the same”. 

'Born in Time' – Tell Tale Signs: The Bootleg Series Vol 8 (2008)

Though unanimously celebrated as a songwriter, there are occasions, where whether through performance or potential, Dylan fumbles the ball a little. The 'Born in Time' that features on 1990’s Born in Time is a poor effort on both counts. However, a Daniel Lanois produced rendition, recorded during the Oh Mercy sessions prove the track's worth, sharing that album’s nocturnal moodiness in addition to a more reflective and emotive vocal, proving that premier versions for even Bob’s misfires often exist somewhere.

'Farewell, Angelina' - The Bootleg Series 1-3 (1991)

Another track Bob cast aside only to be picked up and dusted off by others; notably Baez once again, who is ironically is potentially the subject at hand. In this apocalyptic allegory of the end days of a relationship, King Kong and elves dance upon rooftops, machine guns roar, and the sky burns with embarrassment, it’s the sort of brilliant surreal fairty-tale imagery he would continue to conjure up on later classics like 'Desolation Row'.

'Abandoned Love' – Biograph (1985)

Missing out on a spot on Desire (to his middling mobster biopic 'Joey' of all things) and having only been performed once, perhaps this was a song too close to the bone. Lyrically it does feel more at home on something like Blood on The Tracks than its follow up, with Dylan battling head vs heart amidst the looming end of a relationship. Its exclusion from a proper album makes it another casualty in his catalogue of classics tossed aside. 

'Pay in Blood' – Tempest (2012) 

Late-era Dylan can easily get overlooked, understandable considering he spent three records covering Sinatra-era American standards whilst sounding as though he was gargling gravel, but there is gold to be found in his later material. Despite this song’s gentle groove and swing, Dylan is at his most scathing, swiping at “politicians pumping out the piss” and brandishing “dogs that will tear you limb from limb”. Lord help those on the receiving end of old-man’s wrath.

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More about: Bob Dylan11 underrated