Inventory “Alice’s Restaurant” doesn’t live here: 42 10+ minute “pop” songs worth your time

1. Neil Young, “Cowgirl In The Sand” (10:06)
Neil Young has a knack for making 10 minutes sound like not nearly long enough. On “Cowgirl In The Sand,” from his first album with Crazy Horse—the unstoppable Everybody Knows This Is Nowhere—Young sets a template that he’d repeat plenty of times in the future: Start with a gentle pop song and then let your guitar do the talking for a few minutes. “Cowgirl” never feels wanky, even as it offers up gnarly solos for minutes at a time.

2. Low, “Do You Know How To Waltz?” (14:37) 
The longest song by Duluth, Minnesota’s finest export starts with two minutes of slowly building rumble before a snare snap signals that its heart has arrived. Then husband and wife Alan Sparhawk and Mimi Parker sadly harmonize for a couple of minutes before giving the epic “Do You Know How To Waltz?” back to instrumental rumble, which builds ominously for another 10. It was the first time this quiet band decided to get sort of loud, and they did so in epic fashion.

3. Bob Dylan, “Desolation Row” (11:21)
Bob Dylan’s first real rock ’n’ roll album, Highway 61 Revisited is rightly celebrated as a landmark in his musical progression from baby-faced folk singer to hard-edged pop star. But Dylan’s newfound proclivity for hopped-up rhythm and blues wasn’t nearly as innovative as his surreally evocative lyrics, which poured out of him in a hypnotic, stream-of-consciousness blur that often went on and on for several minutes. While mid-’60s radio stations somehow found room for more than six minutes of “Like A Rolling Stone,” there was no accounting for Highway 61’s sprawling closing track, “Desolation Row.” Stretching a song comprised only of two acoustic guitars and two gut-busting harmonica solos to the breaking point, Dylan justified all 11 minutes and 21 seconds of “Desolation Row” by turning out one great line after another, summing up the ’60s at the decade’s midpoint and predicting much of what came after in the country’s emerging counter-culture. 

4. Television, “Marquee Moon” (10:40)
Punk was supposed to be defined by amateur enthusiasm and short, back-to-the-roots songs. So maybe that’s why, despite being one of the most important bands to emerge from the hothouse of mid-’70s New York, Television never really fit in anywhere. Singer and chief songwriter Tom Verlaine shared the Talking Heads’ art school sensibilities, but the snaky, crystalline guitar sound he and Richard Lloyd created was its own beast. Television twists and stretches throughout its 1977 debut, nowhere as freely as on the title track, a nervous, sprawling centerpiece in which Lloyd and Verlaine offer a primer on new ways to bend, shape, and truncate the sounds made by electric guitars. 

5. The Velvet Underground, “Sister Ray” (17:27)
Considering that amphetamines were supposedly The Velvet Underground’s drug of choice during the White Light/White Heat sessions, “Sister Ray” could have been much, much longer. (Live, it often was: The longest of the three versions collected on Bootleg Series Volume 1: The Quine Tapes spans 38 minutes.) Echoing the orgy-gone-awry portrayed in Lou Reed’s lyrics, the song begins as a standard three-chord rager before devolving into improvisational chaos, balanced between stabs of Reed’s guitar and John Cale’s distorted organ. As if stuck in a nightmare or attempting to piece together details the morning after, Reed loops back to the scene (“She said ‘I couldn't hit it sideways’”), his repetition goaded on by the always-steady hands of drummer Maureen Tucker. The single take that yielded “Sister Ray” was apparently a real nightmare for the recording engineer: He reportedly walked out on the session, leaving the speeding Velvets to come to their own conclusion.    

6. Of Montreal, “The Past Is A Grotesque Animal” (11:52)
Of Montreal’s Hissing Fauna, Are You The Destroyer? has been called a breakup album as well as a tale of Kevin Barnes’ shift towards Georgie Fruit, his glam-rock alter ego. Plopped in the middle is “The Past Is A Grotesque Animal,” nearly 12 minutes of repetitive minor-chord guitar riffs, sinister/seductive backing vocals, and lyrics delving into things like Georges Bataille and the thought, “I’ve explored you with the detachment of an analyst.”

7. Mastodon, “The Last Baron” (13:01)
Atlanta metal monster Mastodon isn’t known for going small, and the group’s 2009 album Crack The Skye is stocked with plenty of sturm, drang, and even a multi-movement mini-opus in the form of “The Czar.” But it’s the disc's closer, the sprawling, prog-heavy “The Last Baron,” that shows Mastodon to be as gargantuan as its namesake. Densely layered and conceptual, the song is the fitting conclusion to an album that integrates personal tragedy (the suicide of drummer Brann Dailor’s teenage sister) into Russian history and wormholes and shit.

8. Joanna Newsom, “Only Skin” (16:53)
Not that the whole song isn’t great, but it’s worth sticking with “Only Skin,” from Joanna Newsom’s ornate Ys, for a moment that comes near its end: Having spun unpredictably from apocalyptic vignette to apocalyptic vignette, Newsom’s cracking fairy voice is met by the deadpan baritone of Smog’s Bill Callahan. As Van Dyke Parks’ orchestra swells behind them, the duo exchanges lines of despair and devotion with a chorus of overdubbed Newsoms, until the chorus delivers the final blow: “I love you truly, or I love no one.” Somehow, in a nearly 20-minute meditation on the fleeting nature of life, that line is the most crushing sentiment.

9. Modest Mouse, “Trucker’s Atlas” (10:57)
On their last album before slicking things up a little bit—the fan-favorite Lonesome Crowded West—Modest Mouse delivered the ornery “Trucker’s Atlas,” which alternates between Isaac Brock’s bark and a sweet little speak-sing. About halfway through, the travelogue gives way to a sloppily hypnotic jam that never sounds too jammy.

10. Neurosis, “Purify” (12:18)
Experimental metal legend Neurosis has never been known for either brevity or levity. But “Purify,” the centerpiece of the group’s monstrously epic 1996 album Through Silver In Blood, is arguably the most sonically dense and richly textured piece of music the band has recorded. With ocean-sized riffs, cosmic stretches of howling emptiness, and the most perverse, horrific abuse of bagpipes ever, it just doesn’t get any vaster than this.

11. Yes, “Heart Of The Sunrise” (11:27)
Given a minor revival by its inclusion in Vincent Gallo’s Buffalo 66, the 1972 Yes song “Heart Of The Sunrise” is an equally disjointed yet lulling piece of work. After a karate-chop blitzkrieg of sharp riffs and shifting meter, the song switches gears into churning, off-kilter funk made all the stranger by Jon Anderson’s forlorn wail. By the time the opening theme reasserts itself, a strangely pleasing exhaustion sets in. When it comes to prog-rock endurance tests, “Sunrise” may be the genre’s catchiest and most tuneful.

12. Stereolab, “Jenny Ondioline” (18:08) 
On this centerpiece track from Stereolab’s benchmark Transient Random-Noise Bursts With Announcements, you can hear the band honing what would come to be its definitive sound, taking its earlier, noisier garage-rock guitar churn and applying it to a hypnotic groove, then slowly bringing in layers of droning synthesizers and the dreamy, insistent harmonies of Laetitia Sadier and Mary Hansen until the whole thing becomes a beautiful mess. “Jenny Ondioline” became such a signature song for Stereolab (while Hansen was still alive) that no live set was complete without it popping in for an encore, ensuring fans always got their money’s worth.

13. Wilco, “Spiders (Kidsmoke)” (10:46) 
Fans notoriously ragged on “Spiders (Kidsmoke)” as an example of why musicians—and specifically one prone to self-indulgence like Jeff Tweedy—shouldn’t craft songs solely on ProTools. But while the cyclical “Spiders (Kidsmoke)” occasionally overstays its welcome (did we really need to hear that whole middle section again?), the song’s attempt to fuse crunchy pop-rock breakdowns and skronk-y no-wave jitters to a propulsive Krautrock thrum succeeds more than it fails—and that Wilco put itself out there at all provided a compelling argument for its greatness. It’s the rare experiment that ends up defining a band.

14. Led Zeppelin, “Achilles Last Stand” (10:25)
While Led Zeppelin partook in many extended jams prior to “Achilles Last Stand”—including Physical Graffiti’s 11-minute version of the blues standard “In My Time Of Dying”—it wasn't until “Achilles Last Stand,” the opening track of 1976’s Presence, that the band really stretched out. Breaking starkly from its bread-and-butter folk ballads and blues-based stompers, “Achilles” is an angular, almost alien-sounding juggernaut of rock that feels harder, colder, and stranger the longer it goes on (and on and on).

15. Public Image Ltd., “Albatross” (10:32)
Before it was about being a caricature of someone being irritating, John Lydon’s entire career was based on being actually irritating. This was never clearer than on this track from Public Image Ltd.’s Metal Box, which seems specifically calculated to make record executives nervous. Yet somewhere in Lydon’s tuneless caterwaul about “getting rid of the albatross,” the monotone, dub-derived burble of Jah Wobble’s bass, and the needling shards of Keith Levene’s guitar lies one of the most alienating post-punk songs ever committed to tape—a coldly aloof spirit that only makes it more attractive. For all the thousands of similarly poker-faced disco-punk imitators that have sprung up in the last decade, “Albatross” is their blueprint.

16. Suicide, “Frankie Teardrop” (10:25) 
In truth, “Frankie Teardrop” barely qualifies as music: It’s really just 10-plus minutes of bone-rattling static pings, far-off drones, and Alan Vega stage-whispering when he’s not letting loose with a bloodcurdling scream or a series of maniacal yips. The lyrics tell a back-alley ghost story about a man named Frankie who can’t make ends meet, so he kills his wife and his 6-month-old kid, then ends up in hell—subject matter so disturbing, apparently, that Nick Hornby wrote in his 31 Songs that he was still afraid of it despite not having listened in 20 years. But there’s something so primal about “Frankie Teardrop,” something so casual about its madness, that it cuts deeper than any number of churning death metal songs that try grasping for the same effect. “Frankie Teardrop” may not be music, technically, but it’s still an arresting example of the power of song. 

17. Kraftwerk, “Autobahn” (22:43)
American listeners who made “Autobahn” Kraftwerk’s first Top 40 hit in 1975 must have been shocked when they picked up the album of the same name: The single was a crisp three and a half minutes long, but the album version was as long as a typical sitcom. That was no accident; Ralf Hütter and Florian Schneider designed the hypnotic, heavily machine-processed song to sound like an inter-city car trip. They would never indulge themselves at quite that length again, but the sound of the song, with its ticking bass, electronic percussion, and mechanical feel would go on to become a huge influence on techno.

18. The Dismemberment Plan, “Respect Is Due” (12:35)
Constructed slowly over a snaking, minimal backbeat, “Respect Is Due” appears to be The Dismemberment Plan’s weary goodbye to a relationship well past its expiration date. Long pauses, whispered grievances, and the occasional sarcastic quip create an air of almost-but-not-quite-indifference that would serve well as the last track on the breakup mix to end all breakup mixes. The chorus, delivered at increasingly higher tempos and tones starting around the 10-minute mark (repeated a dozen times to double as the closing verse), winds up brutal in both its volume and irrevocability: “If I ever would let down the walls that protect me from you / I would say respect is due / but not in this lifetime.”

19. Beastie Boys, “B-Boy Bouillabaisse” (12:33)
Nowhere is Paul’s Boutique Olympian ambition, conceptual brilliance, and kaleidoscopic sonic palette more apparent or transcendent than in its mind-bending final track, “B-Boy Bouillabaisse,” a blunted statement of purpose that shuffles effortlessly between goofball old-school bravado, greasy, Meters-style funk, Isley Brothers guitar heroics, Johnny Cash, and disco. It’s a magnum opus that sums up in 12 and a half minutes where the trio came from and points to where it's headed. With “B-Boy Bouillabaisse,” the New York pranksters/closet idealists defiantly, permanently made the leap from boys to men, from pop stars to major artists.

20. The Sugarhill Gang, “Rapper’s Delight” (14:37)
The Sugarhill Gang’s revolutionary 1979 hit “Rapper’s Delight” brought hip-hop from the streets and park jams of New York to radio, record players, and the mainstream. It was hip-hop’s big bang, commercially at least, but it was more Pat Boone than Chuck Berry. Big Bank Hank famously “borrowed” hip-hop pioneer Grandmaster Caz’s rhymes without credit or contributions, and the group itself was a creation of Sugar Hill Records founder Sylvia Robinson. The nearly 15-minute song features the trio seemingly rapping the contents of their entire rhyme notebooks and the notebook of at least one more talented contemporary. Building on the infectious beat of Chic’s “Good Times” is feel-good pop-rap that made hip-hop accessible to the broadest possible audience and paved the way for pop-rap superstars to come, from MC Hammer to DJ Jazzy Jeff And The Fresh Prince. 

21. Sun Kil Moon, “Duk Koo Kim” (14:32)
Before borrowing and tweaking a South Korean boxer’s name for his Sun Kil Moon project, Mark Kozelek turned his attention to another South Korean fighter for this song, which the former Red House Painters leader has performed under all three of his guises. It first appeared on record in two different forms via a limited-edition 10-inch on Cameron Crowe’s Vinyl Films label (in 10:35 studio and 9:15 live versions, both done solo-acoustic), but Kozelek went all out on this 14-and-a-half-minute full-band take found on Sun Kil Moon’s debut, 2003’s Ghosts Of The Great Highway. While the lyrics do cover the fatal 1982 fight between Ray Mancini and Kim that left the latter “without face, without crown / and the angel who looked upon / she never came down,” it’s just part of a larger reflection on mortality and good old-fashioned carpe diem. The music—split up, more or less, into three parts—couldn’t be more beautiful and dreamy, and it’s hard to shake the words that come around the first transition: “You never know what day’s gonna pick you baby / out of the air, out of nowhere / Oh, come to me once more my love / show me love I’ve never known.”