What is Bob Dylan’s longest song?

Being Hollywood’s elusive man of the hour is, in many ways, merely just another string to Bob Dylan’s bow. Whether as the subject of a blockbuster biopic, as an artist or as a musician, at the heart of the Dylan enigma is the art of storytelling – the all-consuming worlds brought to life in his lyrics are quite simply unparalleled to any other musical force in the industry.

Across Dylan’s sprawling back catalogue, many songs stick out for their own golden nuggets of history across the lyricist’s mighty career, with some admittedly more profoundly seismic than others – ‘Blowin’ in the Wind’, obviously for one, as the breakout to The Freewheelin’ Bob Dylan and the anthemic beacon of the civil rights movement, right down to the unfortunate runt of the litter, ‘Wiggle Wiggle’ from 1990, roundly regarded by fans and critics alike as Dylan’s ultimate clanger.

But naturally, even in the moments he fails to execute it to the best of his ability, the prolific storyteller in Dylan is bound to get wrapped up in the words a little too deeply sometimes and, as a result, produce tracks that more closely resemble epic poems than they do songs. That’s certainly true by the length of many of his records, but his longest song, in particular, takes on a new sonic realm of not only time but lyrical exploration.

So, which is Bob Dylan’s longest tune?

Clocking in at some 16 minutes and 56 seconds, Dylan’s longest song is a relatively recent addition to the canon in the form of ‘Murder Most Foul’, the concluding track taken from his 2020 album and 39th studio record, Rough and Rowdy Ways. It narrowly eclipsed 1997’s ‘Highlands’ – at 16 minutes and 34 seconds – for the top spot, making it Dylan’s lengthiest ode and one of his most fascinating critical gems.

In order for him to feel the need for such a rambling lamentation, the subject of ‘Murder Most Foul’ is one plainly close to Dylan’s heart. It dissects the assassination of President John F Kennedy and the ramifications this has held ever since across the span of American cultural and political life, with the wordsmith acting as the omniscient, all-seeing overlord to a landscape defined by such events.

Dylan’s draw to Kennedy, however, is an interesting facet of his identity which charts back for as long as he himself has been a musician. His initial rise to prominence in the early 1960s came at the height of Kennedy’s administration, and though he protested to the contrary, the assassination of the president in 1963 had a profound impact on Dylan’s personal and artistic psyche ever since, with ‘Murder Most Foul’ the eventual result of decades’ worth of contemplation.

Despite this, the artist claims the song is less about Kennedy himself as a public figure, than it is about how the public responds to mass tragedies and how music can help to heal traumas. Inadvertently, this stood up to contention in the moment of its release, in the most chaotic days of the pandemic lockdown, when the world was forced to a standstill and merely stood in dumbfounded shock. To that end, Dylan’s accompanying statement to the single was that it was a love letter to fans who had stuck by him over the years – a long letter at that – casting back over a defiant career with thousands of defining moments. Whether in 1960 or 2020, you can’t help but get caught up by the legend in that wake.

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