Was it the 20th day of recording “Expecting To Fly” that changed the course of Neil Young’s life? Or was it the 21st?

The year was 1967, and the Buffalo Springfield singer-songwriter-guitarist had quit the band—not for the first time, and not for the last—and ridden off into Sunset Sound in Hollywood with producer Jack Nitzsche. Inspired by the polished, layered sound of The Beach Boys’ Pet Sounds, Young and Nitzsche spent a month working on one song: “Expecting To Fly,” a lilting ballad that Nitzsche enhanced with an orchestral arrangement and multi-tracked vocals. With Buffalo Springfield, Young had grown accustomed to assembling songs piecemeal in a studio, carefully buffing each part; and when Young recorded his first solo album in 1968, he worked much the same way, piling on overdubs. But the obsessive tinkering consumed Young in a way he found unhealthy; and around that same time he became entranced by a local L.A. bar band called The Rockets, who played the kind of loose, country-tinged garage rock Young loved. So there’d be no more “Expecting To Fly”-like experiences in Young’s recording career post-1968. Some Young albums have been more produced than others, but for the most part over the last 45 years, Young has followed the advice of his late collaborator David Briggs: “Put the correct mic in front of the source, get it to the tape the shortest possible route—that’s how you get a great sound.”

Not long after meeting The Rockets—a band he’d commandeer as his own, and rename Crazy Horse—Young picked up a movie camera and started experimenting, operating under the same grip-it-and-rip-it principle he’d begun applying to his music. Filmmaking is a discipline that favors people willing to spend hours lining up a shot and rehearsing a performance, and the push-and-pull between the technical demands of movies and Young’s “the more you think, the more you stink” philosophy (borrowed from Briggs) has produced a body of work that hasn’t exactly made cineastes forget Orson Welles. But like a lot of talented dabblers throughout the history of cinema, Young’s rawness has often proved more personally revealing than work made by directors with way more knowhow.

“Young’s instincts as a musician and his instincts as a filmmaker dovetail in the way he shoots quickly and improvisationally, and then figures out later how to use it all.”

Young first loosed his hobby onto the world at the the height of his commercial success, after the multi-platinum 1972 album Harvest, when he had enough clout to get Warner Bros. to release Journey Through The Past, a full-length movie he’d made in his spare time. Using the alias “Bernard Shakey” (a reference to his own periodic bouts with epilepsy), Young has gone on to make a handful of features: the 1979 concert film Rust Never Sleeps, 1982’s sci-fi comedy Human Highway, 2003’s activist rock opera Greendale, and the confrontational 2008 tour documentary CSNY/Déjà Vu. A packrat by nature, Young has divided his time between recording nearly everything he’s done and sorting through those archives looking for renewal. Making movies has been yet another way for Young to collate and categorize his obsessions, and make some sense of himself.

Journey Through The Past is Young’s first grand statement of purpose. After leaving Buffalo Springfield for good, Young recorded four strikingly different solo albums, and contributed songs to supergroup Crosby, Stills & Nash’s second album Déjà Vu, which brought him to wider public attention. Journey Through The Past includes electrifying archival TV performances by Buffalo Springfield, and intimate backstage and concert footage of CSNY (reportedly swiped from Young’s friend Gary Burden, who was working on his own documentary before Young horned in), and it wouldn’t have taken much for Young to turn Journey Through The Past into a likable, tuneful bio-doc targeted at his millions of new fans.

Instead, Young released a cinematic sketchbook, combining shapeless “a day in the life of Neil Young” scenes and elaborately staged dream sequences into an Alejandro Jodorowsky-esque “head movie” that doubled as a memo on the state of hippiedom circa 1972. In his memoir Waging Heavy Peace, Young writes, “My favorite filmmaker was Jean-Luc Godard. I loved long, uninterrupted shots that played out and told a story. I was not a big fan of fast cutting and preferred to not use dissolves.” His Journey Through The Past had no script, and little in the way of structure. Young just took some of the documentary footage he’d been accumulating in the early 1970s, and added strange pieces of heavily metaphorical visual poetry: a longhair in a graduation gown roaming down the Vegas strip; a hollowed-out Bible with a syringe inside; black-robed cross-bearers on horseback; and more along those lines. “I didn’t make the film to teach anybody anything or to preach to anybody,” Young says in Jimmy McDonough’s biography Shakey. “I did it to express myself.”

Fans of Young as a musician can find a lot in Journey Through The Past that’s revelatory. The scenes of Young recording songs for Harvest in a barn, live to tape, is a valuable document of how he’s continued to make even his more polished albums: holding himself to what he’s called “audio verité,” capturing not just songs but moments. There’s a tremendous amount of pressure to that method. It’s unfussy, and has allowed Young to make a lot of records, but musicians who’ve worked with Young have talked about how disconcerting it can be to move on to the next song before they’ve gotten fully warmed up on the previous one. In this model, Young’s performance in particular becomes more crucial, since he has to guide his accompanists and give a song dramatic purpose, all at once. He’s both actor and director.

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At the time, Journey Through The Past struck some critics and fans as part of a campaign by Young to sabotage his career, post-Harvest. (In the liner notes to the 1977 triple-album anthology Decade, Young wrote of his No. 1 hit “Heart Of Gold,” “This song put me in the middle of the road. Traveling there soon became a bore, so I headed for the ditch.”) But Young’s descent into uncommercial murk wasn’t all that calculated, really. He was drunk and/or high a lot back then, and reacting impulsively to multiple bad situations: the deaths of close friends, the dissolution of romantic relationships, and the realization that his first son, Zeke, had cerebral palsy. Young actually meant to record a proper follow-up to Harvest, but when he couldn’t get the band in his barn to play a strong batch of songs as well as he liked, he decided to record the new material in concert, in front of audiences that hadn’t paid to hear it, with musicians who still hadn’t figured out how to play it, on equipment ill-suited to the task. The resulting album, Time Fades Away, suggests the greatness that might’ve been—but not strongly enough. For the next several years, Young recorded one masterpiece after another in intense, raucous sessions followed by intense, raucous tours. But he’d gained a reputation for being sloppy and flighty, releasing albums cobbled together from different eras—the musical equivalent of Journey Through The Past.

But then Young released Decade, which compiled some of his most memorable songs in a way that made his wilderness years seem more fruitful. He followed that with 1978’s Comes A Time, a pleasant country-rock record that became his best-selling album since Harvest; and then 1979’s Rust Never Sleeps, a half-acoustic, half-electric album recorded in concert, just like Time Fades Away (only with much better sound). Comes A Time showed Young was still capable of writing popular songs, while the material on Rust Never Sleeps—which attempted to reconcile the fading 1960s dream with the punky late 1970s—showed a clarity and engagement that wowed the cognoscenti.

What better time to make another movie?

Superficially, Rust Never Sleeps is Young’s most straightforward film, in that it’s just a performance piece, capturing one night from Young’s Rust tour. But the tour itself featured gimmicks aplenty. Like the album, the stage show starts with an acoustic set, before Crazy Horse joins Young on stage. And throughout, roadies dressed like the Jawas from Star Wars—called “Road Eyes,” because they have automobile headlights where their eyes should be—scurry about, moving comically oversized equipment into place. Rust Never Sleeps lets the shots of the Road Eyes go on for a long time, amplifying their footsteps as they bumble about or dance to the music.

As with Journey Through The Past, the visual component of Rust Never Sleeps is as important as the music. The whole show is pitched as a dream—at one point, Young even lies down on the stage and goes to sleep—as though rock ’n’ roll and the 1960s generation were as much of a fantasy as anything George Lucas could imagine. Between performances, the PA plays Beatles and Jimi Hendrix songs, and Woodstock stage announcements; and at one point, a smarmy announcer tells the audience to put on 3-D glasses so they can experience “Rust-o-vision.” The defining pictures, sounds, and moments of the 20th century exist in a haze in Rust Never Sleeps, enveloping everyone, with everyone equally entitled to pluck from it.

This idea is plainest in the song “My My, Hey Hey,” and its line, “The King is gone but he’s not forgotten / This is the story of Johnny Rotten.” (Or, “Is this the story of Johnny Rotten?” in the furious electric version of the song, “Hey Hey, My My.”) In 1978, a weathered hippie comparing the late Elvis Presley to the lead singer of the Sex Pistols was tantamount to blasphemy, but in the film, Young elaborates on the lyrics even further by showing his own long shadow across the stage, emphasizing the impact that one performer can have. In Young’s eyes, it doesn’t take virtuosity to become a legend. Even the great Hendrix was all about feel, not skill. “It’s easy to play if you can figure out just what he was doin’,” Young says of Hendrix in Shakey. “All the little things, the little nuances—where he pulled his hand off and where he releases the note—it’s not the notes he plays, it’s the way he plays them.”

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Rust Never Sleeps seemed to signal that Young had turned his career around, but once again, his art was knocked askew by his life. His second son, Ben, was born with more complicated and time-consuming health problems than Zeke’s. Also, Young signed a contract with a new record label, Geffen, that had no patience with his efforts to unlock his suddenly stubborn muse by dabbling in electronic music, retro-rockabilly, and straight country. Young spent most of the 1980s making albums his fans didn’t buy and critics didn’t get—in part because, while they were well-meaning, they weren’t that good.

Young effectively kicked off this era with his third film, Human Highway. Shot between 1978 and 1981, Human Highway was Young’s first attempt at a long-form narrative, though because it took so long to make, the movie ended up being another Bernard Shakey hodgepodge of abstract ideas and performances. It’s ostensibly the story of an optimistic boob named Lionel (played by Young), who works as a mechanic in the shadow of a sloppily managed nuclear power plant, and dreams of being a rock star like his hero Frankie Fontaine (also Young). Padded with digressions, Human Highway is confused both stylistically and musically, mixing songs from the folky Comes A Time, the harder-rocking Rust Never Sleeps, and Young’s critically lambasted technopop album Trans—along with performances by the seminal new wave act Devo, whom Young had unexpectedly come to admire. In Shakey, Young says of Human Highway, “I like something that’s so unreal that you could believe it—where the set is obviously phony. Jerry Lewis movies, Japanese horror movies, The Wizard Of Oz—it’s all in there.” He adds, “The movie was made up on the spot by punks, potheads, and former alcoholics.”

In Waging Heavy Peace, Young says of Human Highway, “It is the dorkiest damn movie ever and it walks a very fine line right on the edge of being too dorky.” Yet Young has spent the past several years working off-and-on to re-edit the film and get it onto Netflix—which he should, because as ramshackle as Human Highway is, it’s an entertaining movie, and not all that heavy-handed for an anti-nuke fairy tale. Years before Dean Stockwell, Dennis Hopper, and Russ Tamblyn worked with David Lynch, they helped Young concoct an aggressively weird movie about rock stars, radioactivity, and the lost spiritual connection between humanity and planet Earth. Like so much of Young’s cinematic oeuvre, Human Highway tries too hard to throw a rope around his various musical and real-world interests, but it’s more consistently cinematic than anything Young had done before, taking surreal setpieces like the ones in Journey Through The Past and linking them into something like a live-action Ralph Bakshi film, full of druggy jive and attitude.

[Note: Because Human Highway is only available on Macrovision-protected VHS, the clip below was compiled in Young’s lo-fi spirit, by aiming a cell-phone camera at a TV screen.]

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Young pulled out of his critical and commercial tailspin in 1989, with the album Freedom—one of those odds-and-ends records that Young used to get pilloried for in the 1970s—and while his music from 1990 on has been greeted with a mix of raves and shrugs, Young himself has become more accepted for who he is and what he does. He does still ruffle feathers occasionally, though. In 2006, Young reunited with Crosby, Stills & Nash for what could’ve been a typical dinosaur-act tour, with four old men playing ancient hits for adoring fans. Instead, Young recorded his angriest (and most monotonous) album, the anti-Bush screed Living With War, and played those songs with CSN in front of audiences who were either scandalized, galvanized, or bored. He then turned the “Freedom Of Speech Tour” into the film CSNY/Déjà Vu, which deemphasizes the live performances and deals more with the mixed reactions of the fans.

In typical Young fashion, the concept for Déjà Vu is partially recycled. In the 1980s, Young shot footage for a film he was going to call Muddy Truck, mostly consisting of backstage squabbling and crowd reactions on one troubled European tour with Crazy Horse. (Some of that footage later made it into Jim Jarmusch’s concert film Year Of The Horse.) In Shakey, Young describes Muddy Truck as “the most distorted thing.” The main problem with Déjà Vu is that it’s not distorted enough. It has the style and tone of an extended 60 Minutes segment, with actual war correspondent Mike Cerre “embedded” with the band as it rolls from liberal enclaves like New York and Chicago to hostile territory like Atlanta.

At its best, though, Déjà Vu tries to make sense of Crosby, Stills, Nash, and Young as a group, with clips of them playing together in the 1970s and 1980s intercut with the 2006 shows, illustrating how they’ve fallen in and out of synch over the years. And while Déjà Vu is unapologetically anti-war and anti-Bush, it gives an honest voice to people who weren’t on-board with the tour’s mission, from concert-goers who stormed out of the arena to music critics who found the shows self-indulgent and hypocritical, given how much the band was charging people to preach to them. As a piece of filmmaking, Déjà Vu is disappointingly plain, but it does serve as an explanation of an event that was often misunderstood from the outside. At one point, Stills says, “This is a political cartoon… take it in the spirit it’s intended.” Young is even more philosophical, saying, “You gotta have some reason for being there, or there’s no reason for being there.”

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Déjà Vu isn’t the most divisive project Young was involved with in the 2000s; that honor goes to Greendale, released in 2003 as an audio recording, lo-fi movie, and concert. A “novel with music,” Greendale began life in a focused burst of creativity from Young, in which he walked around his ranch for days with a notepad, sketching out his image of a small coastal California town and the mix of artists, blue-collar workers, criminals, and activists who live there. Like Déjà Vu, the project is a document of a moment in time, dealing with how war and environmental devastation was affecting ordinary people in the new millennium. But Greendale’s songs aren’t “songs” in the conventional Neil Young sense; they’re more like prose stories set to droning rock jams. And as has been his habit throughout his career, Young workshopped Greendale in front of paying audiences, some of whom were livid at shelling out money for a hookless, hard-to-follow, 80-minute story with a blunt political message.

The process paid off, though, because Greendale is Young’s best film: a beautifully conceived and executed formal exercise in which simplicity and complexity collide. Young shot what amounts to a short film for each of Greendale’s songs, literally translating their lyrics into the actions of actors on sets, and having those actors mouth along with the lyrics to simulate dialogue. It’s an impressive feat of staging and choreography, shot on grainy-looking film, supplemented with James Mazzeo’s drawings and TV news clips of politicians like John Ashcroft and Tom Ridge.

Some of the conceits of Greendale don’t work all that well, such as the literal red-suited devil who walks the streets, spreading the spirit of corporate greed and malice. (That’s Neil Young the political cartoonist bulling through again.) But having actors mouth the songs creates some eerie effects, making it look as though these characters are thinking out loud or having interior monologues, expressing thoughts buried deep. And though Young may have hated dissolves back in his Journey Through The Past days, he uses them beautifully in Greendale, to move between the overtly artificial (the drawings, some of the sets) to the real, and create a dreamy feeling similar to the interstitial pieces of Rust Never Sleeps.

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How much credit does Young actually deserve for his films? Greendale certainly feels like a Young-driven work, as do Human Highway and Journey Through The Past—although the latter two contain chunks pulled in from other sources. But on Rust Never Sleeps and Déjà Vu, while Young’s the mastermind, his crews seem to have had just as much to do with the films’ actual creation. Young himself has often cited his longtime cinematic comrade Larry “L.A.” Johnson as most responsible for helping him realize his visions, though before he died, Johnson deflected that praise back at Young, telling McDonough, “The strength of Neil—and why he’s great to work for—[is that] he will try stuff that people more knowledgeable would never think of trying because they know all the pitfalls. He doesn’t. He’s the naïve explorer.”

Some have found that dilettantism infuriating—although for every fan who’s felt let down by setlists full of unfamiliar songs on Young’s various tours, there are thousands more who’ve grown to love the records that sprung from them, and wish they could’ve been there. He’s infuriated bandmates with the way he’s pulled out of projects at the last minute to go follow his own musical whims, but in his own defense, he cites the months he would’ve wasted with Crosby, Stills & Nash when he could’ve been making On The Beach and Zuma.

“Young picked up a movie camera and started experimenting, operating under the same grip-it-and-rip-it principle he’d begun applying to his music.”

Young’s instincts as a musician and his instincts as a filmmaker dovetail in the way he shoots quickly and improvisationally, and then figures out later how to use it all. In Waging Heavy Peace, Young says he edits his films in the same barn where he has his elaborate model-train layouts, and thinks of the processes similarly, piecing bits together to see if they’re structurally sound. “There are so many ways to model the actions and sounds of a machine like a locomotive,” Young writes. “To me, this is a stimulant. I am fascinated by it, by all of the possibilities.”

With LPs and with film, Young has always balanced his “get it down right away” approach with actual craft, and a curatorial eye. He calls up Crazy Horse to jam, but arrives with actual songs, good enough for countless musicians to have covered them over the decades. And he remembers those songs, sometimes bringing them back years later if they don’t get used at the time. Consider “Like A Hurricane”—the anti-“Expecting To Fly.” Like the movie footage that Young shoots and then sits on until inspiration strikes, “Like A Hurricane” was recorded in 1975 but didn’t make it onto an album until 1977. And the only reason that recording exists at all is because an engineer scrambled to roll tape right as Young was leading Crazy Horse through an arrangement of “Like A Hurricane” for the first and only time.

In Waging Heavy Peace, Young jokes about Human Highway that “it’s not Citizen Kane.” But Young himself is a lot like Kane, taking what he wants and socking it away. Because if he didn’t, where would all those moments go?

Next month: Francis Ford Coppola, vintner.