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The 100 Greatest Neil Young Songs

From tender ballads to raging grunge, the songwriter’s nearly 60-year career has produced some of rock’s most enduring music

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“I’d rather keep changing and lose a lot of people along the way,” Neil Young told Rolling Stone in 1975. “If that’s the price, I’ll pay it. I don’t give a shit if my audience is a hundred or a hundred million.” Over the years, Young has turned that unapologetic sentiment into one of rock’s most durable credos, following his ornery muse wherever it leads him. He’s been a folk-rock superstar and a synth-rock pioneer, a country singer and a rockabilly revivalist, a left-leaning environmental activist and a Reagan supporter, a guy who’s been filling arenas since the Seventies even as he drives his fans nuts with his maverick musical detours. But whether he’s the tender soul singing “Heart of Gold” or the rangy crusader giving us a concept album about his awesome new electric car in 2009, Neil Young is always Neil Young – same creaky voice, same searching lyrics, placing him among the greatest songwriters in rock history.

Young first hit the scene with Buffalo Springfield in 1966, not long before Rolling Stone first hit newsstands. He’s been a regular in our pages ever since. We’ve covered his music for decades — hundreds and hundreds of songs spread over studio LPs, live albums, bootlegs, and tapes that Young has only recently begun to release on his Archives website. Some of them are beloved folk-rock hits; some sound like the work of a cult artist with little interest in hooks or high fidelity; some are just really fucking loud. We’ve narrowed that down to his 100 greatest songs, and tell the inside stories behind each one. Our list draws from every point in his career, proving, among other things, that Young is part of an elite group of Sixties rockers who’ve kept making great music long after their supposed glory days.

All these years later, Neil Young has neither burned out nor faded away. Instead, he’s built one of rock’s great careers by doing whatever he wanted, whenever he wanted.

From Rolling Stone US

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‘Broken Arrow’

Like “Expecting to Fly,” this cinematic montage reflected the psychedelic experimentalism coursing through pop in 1967. It interspersed lyrics about the perils of fame with interludes of jazz piano, circus music, and Buffalo Springfield drummer Dewey Martin singing bits of their song “Mr. Soul.” Young wrote the song during one of the many periods during which he was at odds with the rest of the band. “I wrote this after quitting the group in ’67, due to one of many identity crises,” said Young, who chose the title image because it evoked “being scared and mixed up.” Young and producer Jim Messina painstakingly pieced it together from “over a hundred takes,” as Young later recalled.

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‘Out on the Weekend’

Young had already finished most of Harvest when he made one more trip to Nashville to record additional material. Out of those sessions came this lonely-guy ballad, since covered by everyone from Lady Gaga to Deer Tick’s John McCauley. The song’s self-pitying lyrics are almost a parody of the singer-songwriter genre that Young would soon abandon — previewing the song for a film crew before he cut it, he chuckled at the words as he sang them, as if they were a joke. But his quavery delivery, Ben Keith’s high-lonesome pedal steel, and the spare, terse accompaniment of the Stray Gators show how Young could add depth to a trite sentiment.

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‘Don’t Cry No Tears’

“Zuma was breaking free of the murk,” says Young. “My best records are the ones with Crazy Horse.” Zuma brought the band back together after a three-year hiatus, with new guitarist Frank “Poncho” Sampedro and a restored energy. The LP kicks off with “Don’t Cry No Tears,” which takes its melody and many lyrics from “I Wonder,” a song Young recorded with his high school band the Squires more than a decade earlier. He refashioned the old tune to address his disintegrating relationship with actress Carrie Snodgress. “I would be so overwhelmed with my feelings I would start to cry,” she said years later. “It made Neil crazy.”

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‘From Hank to Hendrix’

Young’s hugely successful 1992 album, Harvest Moon, was touted as his long-awaited return to the acoustic country rock of his biggest hit, Harvest. But the album’s centerpiece ballad, “From Hank to Hendrix,” was a million miles away from wide-eyed post-adolescent yearning. Young mourns a relationship that’s seen big changes come and go, both personal and cultural: “From Marilyn to Madonna, I always loved your smile/Now we’re headed for the big divorce, California-style.” He sang it solo in a memorable Saturday Night Live performance, casting a spell that few performers his age could match — a rock elder sharing a little of his hard-won wisdom.

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‘Southern Man’

“It’s much bigger than Southern Man,” Young said. “It’s White Man.” He was in the midst of a furious fight with his wife, Susan Acevedo, when he recorded “Southern Man.” “She was angry at me for some reason, throwing things,” Young said. “They were crashing against the [studio] door.” The song was an FM staple, inspiring proud Southerner Ronnie Van Zant of Lynyrd Skynyrd to write “Sweet Home Alabama” as a response. Young took it as a good-natured barb, and Van Zant began wearing a Tonight’s the Night T-shirt onstage to show there were no hard feelings. “I’d rather play ‘Sweet Home Alabama’ than ‘Southern Man’ any time,” Young told Rolling Stone.

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‘Tired Eyes’

A Topanga Canyon cocaine deal in 1972, at a house with an orgy going on: It should have been the ultimate California hippie dream, but it turned into a driveway gun battle and a couple of dead dealers. Only Young could have turned these murders into such a beautiful song. “That actually happened to a friend of mine,” Young admitted. “My friend was the guy who shot the other guys. It was just one of those deals that turned bad.” “Tired Eyes” is the elegiac centerpiece of Tonight’s the Night, mourning the casualties of the Sixties, wondering how it all went so wrong. Young strains for high notes he can’t hit, over the ghostly lurch of Ben Keith’s pedal steel and Nils Lofgren’s piano. Young mumbles the chorus — “Please take my advice/Open up the tired eyes” — over and over, as if he’s trying to wake himself up from a nightmare. In the America of the 1970s, he sure wasn’t the only one who knew that feeling. “We all got high enough,” Young later said of the Tonight’s the Night sessions, “right out there on the edge where we felt wide open to the whole mood. It was spooky. I probably feel this album more than anything I’ve ever done.”

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‘Words (Between the Lines of Age)’

Due to painful back problems, Young played acoustic guitar on much of Harvest. “The doctors started talking about wheelchairs and shit, so I had some discs removed,” he said. After surgery, he recorded some songs on electric guitar, including this twisting jam, with guest vocals by Stephen Stills and Graham Nash. A 16-minute version appears on 1972’s Journey Through the Past.

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This gleaming, gut-wrenching love song was first performed by Young solo-acoustic at a club show in Ann Arbor, Michigan, in 1968, and then cut with Crazy Horse the following year. It was shelved until 1974, when it was rerecorded with Ben Keith’s pedal steel standing in for the late Danny Whitten’s guitar. Nixed from the final version of Tonight’s the Night, it finally saw the light of day as a surprise highlight of Decade. For a sense of the Crazy Horse original, check out the serrated version on Live at the Fillmore East, where Whitten and Young poignantly join voices.

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‘Cowgirl in the Sand’

Everybody Knows This Is Nowhere closes with this heady 10-minute jam, a perfect distillation of the chaotic beauty of Crazy Horse’s first incarnation. Young wrote it while he was sick with the flu and recorded it with the band in a single day at his Topanga Canyon basement studio — the same day they knocked out “Cinnamon Girl” and “Down by the River.” “There wasn’t much need to discuss it,” said bassist Billy Talbot. “Cowgirl in the Sand” has gone on to serve as the centerpiece of many Crazy Horse shows over the following decades, often stretching out to 18 minutes or longer (for a definitive experience, listen to the version on Live at the Fillmore East, from 1970). One reason for its live power, according to Young, is the dreamy vagueness of the lyrics. “The words to ‘Cowgirl in the Sand’ are very important because you can free-associate with them,” he said. “Some words won’t let you do that, so you’re locked into the specific fuckin’ thing the guy’s singing about. … This way, it could be anything.”

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‘Rockin’ in the Free World’

In the final months of the 1980s, Young suddenly roared back to life. “Rockin’ in the Free World” delivered what most of Young’s work in that decade had totally lacked: passion, noise, energy, and that madcap Neil Young grin. Guitarist Frank “Poncho” Sampedro remembers coming up with the iconic phrase after seeing newspaper photos of Iranian protesters burning American flags. “Whatever we do, we shouldn’t go near the Mideast,” he remembers saying. “It’s probably better to keep rockin’ in the free world.” Young thought the phrase was “such a cliché” that he had to use it. Two versions of “Rockin’ in the Free World” bookend Freedom – first a live acoustic version, then a stomping electric finale, with Young shredding away on guitar as he rants its lyrics about crack, poverty, the military buildup, and environmental disasters. He introduced the song on Saturday Night Live, raging on guitar in an Elvis T-shirt, as if he’d woken up from a coma, shocking fans around the country. His massive creative resurgence was just beginning.

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‘Expecting to Fly’

According to collaborator Jack Nitzsche, this trippy piece of orchestrated melancholia dealt with Young’s “fear of making it with a girl.” But the song was also a testament to his singular vision at the dawn of his career. Although credited to Buffalo Springfield, it was recorded with session players including drummer Jim Gordon, bassist Carol Kaye, and backup singer Merry Clayton. Young and Nitzsche, his fearless co-producer, spent weeks crafting the grandly spacious record, even the singing. “I overdubbed my vocal line by line to get it in pitch,” Young said. “Studio singing was still very nervous for me then.” When the Beatles’ “A Day in the Life” was released just after “Expecting to Fly” had been completed, Young thought the two songs too similar (particularly their shared hovering, sustained finales) and worked on his track some more. “We had it all ready to go,” he said, “so we just went back into the studio and changed it around.” He needn’t have worried: “Expecting to Fly” is still unlike anything Young had created before — or since.

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‘Sugar Mountain’

Young wrote this paean to youth the month he turned 19. At the time, he was living hand-to-mouth in Toronto, crashing on floors and beginning to play his originals at local folk sessions. Praise for this song in particular “made me feel like I was somebody,” Young later said. Among those he wowed was a young Joni Mitchell, who wrote her early gem “The Circle Game” as an answer song to “Sugar Mountain.” Released at various times as a single B side (initially of “The Loner,” in 1969), the song has remained in Young’s repertoire. One of the more moving stories in Waging Heavy Peace describes his moment of transcendence singing it to an empty stadium in Missouri in 2011, with just a guitar and harmonica, a teenage folk singer come full circle.

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‘The Needle and the Damage Done’

“I’m not a preacher, but drugs killed a lot of great men,” Young says in the Decade liner notes. “The Needle and the Damage Done” laments one of them: Crazy Horse guitarist Danny Whitten. One of rock’s first explicit anti-drug songs, this moving ballad was written as Whitten was being pulled under by his addiction. “He’d gotten so wasted, so strung out,” Young said later. Young tried to get Whitten to play on the tour to support Harvest, but it soon hit the point where he was nodding off in rehearsals. “He was too out of it,” Young told Rolling Stone in 1975. “Too far gone. I had to tell him to go back to L.A.” Young sent Whitten packing with $50 and a plane ticket; the guitarist spent the cash on heroin and was dead within hours. “I sing this song because I loved the man/I know that some of you don’t understand,” he testifies in the lyrics. (In 1971, Young introduced “The Needle and the Damage Done” live by commenting on all the talent he’d seen ruined by heroin — “over and over.”) As Young said later, “I never sat down with him and said, ‘Danny, listen to this.’”

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‘Hey Hey, My My (Into the Black)’

It’s seen by many as the ultimate Crazy Horse anthem, but the first time Young played “Hey Hey, My My,” he was backed by New Wave oddballs Devo. Young was filming the surreal movie Human Highway with the band, and he picked up the expression “rust never sleeps” from frontman Mark Mothersbaugh, who’d heard it in an ad for Rust-Oleum paint. They filmed a wild, frenetic 10-minute version of the song, and months later, when Young asked Crazy Horse to tackle it, they balked. “We were like, ‘Fuck that,’ ” says Frank “Poncho” Sampedro. “ ‘Devo already did it.’ We then watched the video of them playing it, and were so pissed off, we played it three times harder than they ever could — and we still do.” The song closes Rust Never Sleeps with an acerbic commentary on rock’s changing climate (“The king is gone but he’s not forgotten/Is this the story of Johnny Rotten?”), but Kurt Cobain flagged a line from the acoustic version that opened the album in his suicide note: “It’s better to burn out than to fade away.”

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‘Old Man’

Young wrote this front-porch singalong about Louis Avila, the seasoned foreman of the Lazy Double L — a ranch spread in the Santa Cruz Mountains that the 24-year-old rock star, flush with cash, purchased in 1970, renamed the Broken Arrow Ranch, and made into what would become his lifelong home. Like much of Harvest, it was recorded in Nashville with the Stray Gators, and the song also features James Taylor, surprisingly enough, on six-string banjo (“I don’t think I played on one before or since,” notes Taylor). An acoustic meditation on age and life’s through-line — two of Young’s favorite themes; see “Sugar Mountain” — it sweeps past the specifics of its writing to address any sort of cross-generational relationship with respect and reverence. “My dad thought it was written for him,” Young confides in his memoir, “and I never told him it wasn’t, because songs are for whoever receives them.” A highlight of his singer-songwriter phase, it was the last time in his career he would reach the Top 40.

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‘Like a Hurricane’

After an especially fun night out bar-hopping in L.A., Young stopped at a scenic look-out and, in his friend’s car, dashed off lyrics about desire, dreams, and “getting blown away” by it all. Since he’d recently had an operation for nodes on his vocal cords, he couldn’t sing, so he whistled the melody. If only the recording of one of Young and Crazy Horse’s most epic songs — eight minutes of cathedral-size guitar majesty — had been so easy. Young and the band spent 10 days on his ranch trying to nail it. But after endless takes featuring their two-guitar lineup, the song still wasn’t coming together. Then, guitarist Frank “Poncho” Sampedro tried putting down his axe and began fiddling around with the Stringman synthesizer that’s heard on the final version. “Yeah, I think that’s how it goes,” Young told him. “Just like that.” The result is a driving, intensely powerful rocker. “It is one of those performances you can never repeat,” Young said. “We just kept wailing on those changes until we couldn’t move anymore.”

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Two weeks after four student protesters were killed by National Guardsmen at Kent State University, Young saw a photo spread on the incident in Life magazine and was inspired to write this furiously melancholic song, which took the unprecedented step of calling out Richard Nixon by name. He brought Crosby, Stills, and Nash into a Los Angeles studio the next day, and Crosby began weeping uncontrollably after one of the takes. Atlantic Records rushed it to radio stations, even though “Teach Your Children” was then in the Top 20. “We were speaking for our generation, we were speaking for ourselves,” Young said in 2012. “It rang true.” The song became a hit, but CSNY broke up just two months later.

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‘After the Gold Rush’

“CSNY put my name out there, but After the Gold Rush was the turning point,” Young told Rolling Stone’s Cameron Crowe in 1975. Young was talking about his third solo album, and the way it vaulted him into a new class of singer-songwriter success and artistic brilliance. But he could just as easily have been referring to the album’s superb title track, a surreal sci-fi piano ballad about the aftermath of an environmental disaster, complete with the chillingly prophetic line “look at Mother Nature on the run in the 1970s.” Young nicked the title and the idea from a lost screenplay by a friend, the actor Dean Stockwell, about a tidal wave sweeping over Southern California. The movie was never made, but the song, which producer David Briggs recalled Young writing in just half an hour, became one of Young’s most enduring classics. “I would listen to Neil singing that all the time on the road,” said Linda Ronstadt, one of the many artists (including Thom Yorke and Patti Smith) who have tried their hands at cover versions of “Gold Rush.” “I would think, ‘This is the future.’ ”

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‘Cinnamon Girl’

The greatest one-note guitar solo in rock history? No question. Young summed up all the crazed extremes of his music in the three-minute rush of “Cinnamon Girl,” his first successful single as a solo artist. The song showed off his tuneful, romantic side as well as his love for savage guitar feedback. “Cinnamon Girl” was a pop moment of sorts amid the hard rock of Everybody Knows This Is Nowhere, reaching Number 55 on the Billboard charts in the summer of 1970 (“The closest thing Crazy Horse had to a hit record,” Young said). It makes the most of the band’s club-on-the-head approach, climaxing in that proudly anti-virtuosic moment, as Young sails away on a naggingly repetitive one-note clang. He even lets out a “whooo!” of delight, with girl-group-style hand claps (inspired by the Angels’ 1963 hit “My Boyfriend’s Back”) buried in the mix. “Cinnamon Girl” introduced the Neil Young solo style he’d pursue his whole career — and remains one of his evergreen live crowd-pleasers.

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“Helpless” is a heart-rending highlight from Crosby, Stills, Nash, and Young’s Déjà Vu, a slow, beautiful country-rock reverie in which Young spools through childhood images of rural Canada. He did, as the lyrics tell us, grow up in a small town in Ontario (Omemee; population in 1950: 750), but he insists “Helpless” isn’t a simple autobiographical tale. “It’s not literally a specific town,” he said, “so much as a feeling.” The gentle, sweetly nostalgic song was imagined by Young as a thrashed-out Crazy Horse jam, but when a studio technician forgot to press “record” on the band’s best take, Young tried a radically different direction: “I took it as an omen. That’s why I did it with CSN.” It’s the finest song he recorded with the trio; they add lush harmonies, but the rest is strictly Neil. Young has played “Helpless” more than 400 times live, most memorably with the Band at the Last Waltz, where he had so much cocaine visible in his nostrils that director Martin Scorsese had to take it out frame by frame while editing footage for the concert film.

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‘Tonight’s the Night’

The dark inspiration for “Tonight’s the Night” was two almost simultaneous drug deaths in the Crazy Horse family, as Young put it, “The whole thing is about life, dope, and death.” Heroin took the life of guitarist Danny Whitten in 1972, and, less than a year later, their beloved roadie Bruce Berry; Young’s response was this harrowing dead-junkie lament. He mourns Berry as a rock & roll workingman whose honest passion for life was corrupted by drugs. As you can hear, Young and the entire band are in rough shape — drunk, off-key, enraged, wracked by grief and tequila. “We played Bruce and Danny on their way all through the night,” Young told Rolling Stone in 1975. “It was spooky.” Young began and ended Tonight’s the Night, one of his most emotionally intense albums, with ravaged versions of the theme song. “Tonight’s the Night” became an unlikely stadium-shaking rock anthem — the definitive version is the big climax of 1979’s Live Rust, where you can hear the fans whoop, cheer, and whistle along with a funeral dirge.

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‘Down by the River’

The prototype for all Young’s massive Crazy Horse guitar jams to come appeared on his second solo LP, his first with the band and the album that fully announced his arrival as a solo artist in the late Sixties. Young wrote the song during a legendary bout with the flu, one of the most musically consequential 103-degree fevers in rock & roll history, which produced three of his career-defining songs: “Cinnamon Girl,” “Cowgirl in the Sand,” and this. “There was a song in E-minor on the radio that I liked, ‘Sunny’ or something like that,” Young wrote in his memoir Waging Heavy Peace, referring to soul singer Bobby Hebb’s 1966 hit. “[It] kept looping in my head, endlessly, like some things do when I’m sick and maybe a little delirious. So I started playing it on the guitar, and then I changed the chords a bit — and it turned into ‘Down by the River.’” He once dismissed the song’s murderous lyrics, saying, “It’s about blowing your thing with a chick.” But Young’s guitar duels with Danny Whitten on this nine-minute spectacle suggest something different — they play like they’re out for blood.

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‘Cortez the Killer’

It’s never been clearly explained why Young decided to write a (wildly unhistorical) song about the 16th-century Spanish conquistador Hernan Cortés. Over the years, Young has claimed to have authored it on the spot while writing songs for Zuma, but at a 1996 show in Virginia he swore he wrote it in high school after eating six hamburgers and getting terribly sick. “I was studying history, and in the morning I woke up and I’d written this song,” he said. “I never told anybody else.” Whatever the truth, Young and Crazy Horse cut the song one debauched day at Zuma Beach in 1975. Crazy Horse guitarist Frank “Poncho” Sampedro and bassist Billy Talbot smoked angel dust right before the session, but they still managed to help Young create one of the most overpowering guitar epics ever recorded. The electricity went off in the studio midway through recording the song. “We didn’t know and just kept playing and playing,” says Talbot. “We lost a verse, but Neil said it was a good verse to lose.” That explains why the song ends so abruptly. The lost verse has yet to surface anywhere.

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‘Heart of Gold’

Young was all of 27 years old when he sang the chorus of his biggest hit: “Keep me searching for a heart of gold/And I’m gettin’ old.” “Heart of Gold” became his first and only Number One single, the epitome of his mellow, countrified soft-rock phase. Like many songs on the hugely successful Harvest, it was recorded in Nashville with producer Elliot Mazer and a backing band known as the Stray Gators. “Heart of Gold” has Young’s most mournful harmonica-playing, Ben Keith’s steel guitar, and the Tupelo-honey harmonies of Linda Ronstadt and James Taylor. Ironically, the song got bumped from the Number One spot by America’s “A Horse With No Name,” the most shameless Neil Young imitation of all time (it even confused his father, who called to congratulate him). But nobody’s ever duplicated the vulnerable twang of “Heart of Gold,” and to Young’s credit, he steadfastly refused to copy it. Indeed, after his big commercial breakthrough, Young avoided Top 40 radio like the plague. “‘Heart of Gold’ put me in the middle of the road,” he wrote in the liner notes to the 1977 anthology, Decade. “Traveling there soon became a bore, so I headed for the ditch.”

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‘Ambulance Blues’

“It’s easy to get buried in the past/When you try to make a good thing last,” Young sings midway through “Ambulance Blues,” an exquisite reconsideration of the dizzying distance he’d traveled — in space, time, and outlook — since his career began in Toronto’s folk clubs a decade earlier. Gently finger-picking an acoustic melody lifted from Sixties folkie Bert Jansch, Young spends nearly nine minutes at the end of On the Beach’s down-and-out Side B reminiscing about his “old folkie days” at the Riverboat Coffee House. There’s an innocence to the way those scenes play out in his memory, a feeling that’s crushed when he starts talking in code about Mother Goose and a kidnapping plot a few verses later. The skeleton key to this dream? When Young resignedly sings “You’re all just pissin’ in the wind,” he’s reportedly quoting his manager Elliot Roberts’ take on the internal acrimony that broke up CSNY. What began as nostalgia has lapsed into weary bitterness.

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Young’s greatest song contains just about everything that makes Neil Young great: It’s a monster Crazy Horse guitar anthem that has the coming-of-age poignancy of his bittersweet acoustic ballads, channeling themes that have shown up in his work for decades (the myth of the West, the individual’s lonely struggle, mortality, freedom, American violence, and community) into music that’s at once rousing and devastating. Lyrically, Young manages to cram a two-hour Western into a five-minute song. It’s the story of a family of outlaws and the 22-year-old son who has to fend off government troops now that Daddy’s gone. “Neil told me the story came to him in a seizure dream,” says Crazy Horse guitarist Frank “Poncho” Sampedro. “He felt he was out there visiting these people. So that made it all the more vivid.” The song was originally recorded for the aborted Chrome Dreams album in 1975, and was resurrected four years later for Rust Never Sleeps, where it kicks off the roaring electric Side Two. Only at the end of “Powderfinger” do we learn that the tune’s narrator is dead, killed by soldiers as he stood on a dock aiming his gun at their boat in a pathetic attempt to defend his family. “I think the crux of it is anti-violent,” Young wrote. “It shows the futility of violence.” The track wasn’t a single and has never gotten much radio play, but it’s clear Young agrees that “Powderfinger” is one of his finest works. He has played it more than any song in his catalog besides “Cinnamon Girl” and “Heart of Gold.”