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The 10 best songs over nine minutes long

Popular music convention tends to follow an unwritten rule where tracks hit a sweet spot between three and four minutes. If a song is any shorter than three minutes, it’s likely too brief to get into the swing of, and if it surpasses the four-minute mark, most listeners will be tuning out or changing the record. However, this is just the convention for money printing hits that grace the common listener on the radio. 

Following the explosion of experimental music in the 1960s, lengthier compositions became more commonplace. The epics could be found in Bob Dylan’s catalogue to allow him more space to spin his poetic lyrical yarn, or in Pink Floyd’s interminable mindbending odysseys — yes I’m thinking of the unrelenting ‘Atom Heart Mother Suite’ which, for better or worse, goes on and on for over 23 minutes. 

Granted, music should never be too long, while a typical feature film lasts around 90 minutes, I dare a popular musical artist to make a song that long and see how many of their fans stay tuned in for the duration. That said, there have been some songs on the lengthier end of the spectrum that hit the nail on the head, with the extra minutes used wisely, adding to the overall artistic merit of the composition. For example, try listening to ‘Atom Heart Mother Suite’ and then listen to Pink Floyd’s 1971 hit ‘Echoes’. I wager good money that for most, the time spent listening to the fantastic ‘Echoes’ will seemingly pass by quicker despite both tracks near enough tying as Pink Floyd’s longest ever singular songs.

The longest song ever officially released, PC III’s ‘The Rise and Fall of Bossanova’ clocks in at 13 hours and 32 seconds. Fortunately for all of us, that song doesn’t appear on the upcoming list, not because it’s no good, but simply because I haven’t listened to it. The list below will explore my pick of the ten most listenable and creatively alluring songs over nine minutes long.

The 10 best songs over nine minutes:

‘Desolation Row’ – Bob Dylan (11:20)

Our most prized songwriter, Bob Dylan, was certainly no stranger to a beefy composition. In 1966, Dylan finished off his masterpiece album Blonde on Blonde with ‘Sad Eyed Lady of the Lowlands’, which takes up the whole D-side of the double LP release at just over 11 minutes. More recently, Dylan rounded off his 2020 album Rough and Rowdy Ways with ‘Murder Most Foul’, which clocked in at 16 minutes and 54 seconds, making it his longest ever song.

Today, however, I bring your attention to Dylan’s 1965 album Highway 61 Revisited, famed most for its classic hit ‘Like A Rolling Stone’. But the album closes on what I believe to be Dylan’s finest epic, ‘Desolation Row’. The lengthy composition boasts some of Dylan’s most considered and creative lyrics as he weaves a series of familiar characters and events into a torrent of poetic enigma. ‘Desolation Row’ held the title of the longest popular music song briefly, until the Rolling Stones released ‘Goin’ Home’ (11:35) in 1966.

‘The Tower’ – Julian Cope (10:16)

The experimental oddball Julian Cope departed from his humble beginnings as the zany frontman of The Teardrop Explodes in 1983 to pursue his solo career. He was never a stranger to experimenting with psychedelic drugs as a means of exploring the realms of perception and warping reality. He once even found himself tripping on LSD during his Top of the Pops performance of ‘Passionate Friend’ in 1981.

The years of mind-expanding exploration of the mystique certainly steered Cope’s creative direction while fortunately never pushing him into the sad fate of Pink Floyd’s Syd Barrett. Instead, Cope’s music began to delve into religious ideologies and existentialism on an increasingly frequent basis. By the time he was releasing his 1992 album Jehovahkill, he had begun imposing a strange pagan-esque slant in his music. The album is a multifaceted orchard of intrigue, and one of its sweetest fruits is the brilliant ‘The Tower’, which clocks in at just over ten minutes, but I could personally keep it on repeat for an hour.

‘Shine On You Crazy Diamond, Pts. 1-5’ – Pink Floyd (13:29)

Pink Floyd were never those to shy away from a lengthy composition. Their extended jams often become somewhat tired toward the end, leaving the listener wanting to abort some of the interstellar journeys and skip to the next track prematurely. However, ‘Shine On You Crazy Diamond, Pts. 1-5’ is not one of these occasions.

The soaring multi-chaptered epic appears on the group’s 1975 album Wish You Were Here. The nine chapters of ‘Shine On You Crazy Diamond’ were split into two runs with parts one to five being the more popular introduction to the album and parts six to nine follow the other three songs on the album at the end. The composition was written as an ode to the group’s absent founding member Syd Barrett who was forced to leave the group amid a worsening case of LSD induced psychosis. 

‘Sister Ray’ – The Velvet Underground (17:29)

After The Velvet Underground released themselves from the shackles of the creative management of pop artist Andy Warhol, they released their second album White Light/White Heat. This follow-up to The Velvet Underground and Nico was a further step into obscure depravity, continuing the themes of drug abuse and grievous sexual acts, most clearly displayed in the seventeen-minute epic, ‘Sister Ray’. 

As songwriter Lou Reed once described the track: “‘Sister Ray’ was done as a joke—no, not as a joke, but it has eight characters in it, and this guy gets killed, and nobody does anything. It was built around this story that I wrote about this scene of total debauchery and decay. I like to think of ‘Sister Ray’ as a transvestite smack dealer. The situation is a bunch of drag queens taking some sailors home with them, shooting up on smack and having this orgy when the police appear.”

‘Fools Gold’ – The Stone Roses (9:53)

In 1989, The Stone Roses released their eponymous debut album marking both the peak and the beginning of their mainstream success. The album is absolutely littered with timeless alt-rock favourites, including ‘I Wanna Be Adored’, ‘I Am The Resurrection and ‘Waterfall’. 

The album closes on a stunner of an epic in ‘Fools Gold’. The Madchester group had been looking for a funky, danceable number, perhaps to rival their Manchester neighbours Happy Mondays. Ironically, they struck gold with the groovy bassline in ‘Fools Gold’ and rightly opted to make the hit an extended recording.

‘The End’ – The Doors (11:43)

‘The End’ features – you guessed it – at the very end of The Doors’ 1967 debut album. The haunting lyrics began as a break-up song but spiralled into a dark, brooding anthem thanks to the chilling organ, tumbling percussion and prevailing blues-inspired lead guitar. The track was launched back to the fore in 1979 featuring as the opening track on Francis Ford Coppola’s Vietnam War classic film Apocalypse Now.

“Every time I hear that song, it means something else to me. It started out as a simple goodbye song,” Morrison told Rolling Stone in 1969. “Probably just to a girl, but I see how it could be a goodbye to a kind of childhood. I really don’t know. I think it’s sufficiently complex and universal in its imagery that it could be almost anything you want it to be.”

‘Voodoo Chile’ – Jimi Hendrix (15:00)

Jimi Hendrix released his third and final studio album Electric Ladyland in October 1968. The album showed Hendrix at the height of his power as a blues innovator and guitar prodigy. 

The album holds several of Hendrix’s most popular hits, including his arresting cover of Bob Dylan’s ‘All Along the Watchtower’ and the album’s closer ‘Voodoo Child (Slight Return)’. The 15-minute epic, ‘Voodoo Chile’ appears on the album as the earlier and more traditionally structured bluesy incarnation of the album’s closing track. The song started out as ‘Catfish Blues’, a live jam and homage to the blues legend Muddy Waters, of whom the Hendrix had been a great admirer.

‘Achilles Last Stand’ – Led Zeppelin (10:31)

In 1976, Led Zeppelin released their seventh studio album, Presence. The album didn’t live up to the dizzying heights of its predecessor Physical Graffiti, but one of its purest moments – or should I say ten – was undoubtedly ‘Achilles Last Stand’.

Robert Plant once stated that ‘Achilles Last Stand’ and ‘Candy Store Rock’ were the album’s saving grace, thanks to “the rhythm section on that, it was so inspired.” Indeed the tracks laid testament to the raw rhythm talent of bassist John Paul Jones and drummer John Bonham. 

‘Cop Shoot Cop’ – Spiritualized (17:14)

In 1997, J. Spaceman (AKA Jason Pierce), the leader of experimental rock group Spiritualized, released an unmitigated tour de force in Ladies and gentlemen we are floating in space

The album is perfectly balanced with an eclectic taste of music from all corners of music, from classical to psychedelic rock. The bold and brilliant closing track on the double album, ‘Cop Shoot Cop’, begins with a slow bubbling blues-inspired rhythm which, all of a sudden, hurtles the listener into an onslaught of psychedelic mystique before landing back on the ground at around the 12-minute mark as you come around and wonder where your mind had been for the last six minutes.

‘Station To Station’ – David Bowie (10:14)

Following his fling with oil on 1975’s Young Americans, David Bowie came back with a new persona as the Thin White Duke as he introduced us to his fantastic album Station To Station.

The album opens strongly with a bold, compartmentalised epic clocking in at just over ten minutes. The album’s eponymous opening track introduces us to the strange cocaine-fuelled world of the Thin White Duke. The beginning builds up slowly with a desolate and unnerving sound that erupts into colour at the halfway point with a conviction that leaves us hungry for the rest of the landmark album.