Filmmaking isn’t for the fainthearted—just ask Martin Sheen, who suffered a massive coronary episode on the set of Apocalypse Now.

Yep, art is hard. This is no great revelation, of course, because millions of dollars back even the smallest “independent” features nowadays, and an entire international, billion-dollar business is behind the idea that one can’t go at this thing—this glamorous, artistically sought after thing—alone. This likely explains why the filmmakers around whom the greatest production stories evolve are those with egos and personalities as outsized as the films they struggle to make. Either that, or some artists are just doomed to be on the bad side of even worse luck.

Regardless, the stories behind these fabled films—both those that saw the dimmed lights of a theater and those that went unmade—are so ripe for exploration because they are the stories of artistic ambition made flesh. These are stories not only about the people who go to any lengths to satisfy their ineffable creative urges, but about the dirty backside of such idealistic goals. Every artist likes to say that he or she stands behind the tenet that “the ends justify the means,” but deep down, every one of us knows a line must be drawn between the purpose a piece of art serves and the sacrifices incurred in serving that purpose.

So, to accompany this year’s release of yet another “making of” documentary, Lost Soul, a film that tells the embattled narrative of making The Island of Dr. Moreau, we’ve collected a list of 10 films fraught with Phyrric victories, and the 10 documentaries that claim they may’ve been way more trouble than they’re worth.



Director: David Gregory

If Val Kilmer’s Twitter account is any indication, the actor’s ego hasn’t deflated one bit since the filming of 1996’s The Island of Dr. Moreau—it’s only grown so surreally that it now consumes more than one famous personality. (How else would we explain his one man show about Mark Twain?) Shining some light on the true price of hubris in Hollywood, David Gregory’s documentary chronicles the conception of Island and fast-forwards right to its sticky afterbirth: how it was a certifiable box-office disaster, and not only because of star Kilmer notoriously flexing his unpleasant selfdom all over the set, or Marlon Brando’s off-putting antics (marking the first of two films on this list which suffered under Brando’s hefty strangeness), but because original director Richard Stanley’s vision for the H.G. Wells novel was squashed in favor of more typical industry fare. As an account of Hollywood weirdness, cast and crew stories from the production delight, but as a condemnation of wasted creativity, the film reads like an obituary for originality.







Director: Frank Pavich

Here’s a “what-if” documentary that, from the onset, like the sign over Dante’s depiction of Hell, tells you to abandon all hope. This it does in the swaggering anecdote of Nicholas Winding Refn, who claims that he is one of very few people on Earth to have ever “seen” Alejandro Jodorowsky’s never-filmed version of the seminal Frank Herbert sci-fi tome. One drunken night after dinner at Jodorowsky’s abode, the Spanish auteur supposedly pulled out a bound coffee-table-sized book of the unmade film’s complete storyboard, proceeding to narrate the film to the hushed, tipsy Refn. Face it, both Refn and the documentary declare in that moment: Jodorowsky’s Dune will never happen. So just move on already.

This is how the bulk of Jodorowsky’s Dune, the documentary detailing the doomed adaptation, unfolds: we “watch” unmade Dune through Jodorowsky’s oral history, how he obsessively sublimated the hero’s journey at the heart of Herbert’s story into a quest he felt he was taking for the future of visual storytelling. Nothing less would suffice. And, yup, you read that right: his intensity was so unyielding, so complete, that among other batshit stunts, he forced his own son to undergo years of extensive physical and mental training, practically abusing the adolescent in order to get the boy “ready” to play the messianic Paul Atreides.

And from there we’re left with rich imaginings and even richer resentment, mostly because, if we’re supposed to take Jodorowsky’s word for it, we’ve been robbed of a truly life-changing cinematic experience. Instead, we got a stinking facsimile of what Jodorowsky had planned: David Lynch’s cult curio of an adaptation, a certain kind of failure in its own right.

Again, this is just one man’s hubris talking, and by now we should accept that such monumental films require equally monumental minds behind them. Yet, where the documentary succeeds most is in flipping that whole “what-if” scenario on its head. What if the world is better off because Jodorowsky’s Dune was never made? Not only did the fruits of Jodorowsky’s ultimate failure, we’re told, bear the seeds of actual films like Alien, Blade Runner, and, some would say, Star Wars, but the sheer magnificent absurdity of Jodorowsky’s vision may have meant a financial and creative disaster bound to have taken its whole braintrust down with it—not to mention psychologically scar Jodorowsky’s kid in the process.



Directors: Tony Montana, Mark Brian Smith

While Jodorowsky’s Dune is one of many examples that, through chronicling the artistic struggles of a director ahead of his or her time, throws into relief the dysfunction inherent to the Hollywood machine, Overnight claims that maybe Hollywood isn’t so bad after all.

Overnight follows writer/director Troy Duffy as he whines his way through the long uphill slog of making his first film, The Boondock Saints, a debut initially backed by Hollywood heavyweights but abandoned after Duffy revealed himself to be an impossibly uncooperative clown. Today, it’s no surprise that The Boondock Saints hasn’t aged well; in the 15 years since its release, the world seems less apt than ever to stomach its rampant homophobia, misogyny, and idiotic soundtrack—so much so that even its original cult apologists (this author included) have all but admitted it’s a bro’s wet dream best laundered from our collective consciousness.

Overnight does nothing to defend Boondock’s legacy, instead documenting Duffy’s rise to and fall from fame while he spent an inordinate of time, money, and family members’ patience attempting to get his debut through the system that shunned him. The documentary paints Duffy as exactly the kind of guy who you’d imagine would make a film like Boondock Saints: loud, vulgar, petulant, dumb, just … so dumb. There’s really nothing positive to say about him after witnessing his self-immolation, except maybe that he got what he deserved. And if what he deserved was to squander the goodwill of a surprisingly tolerant Hollywood, so much so that Harvey Weinstein notoriously “blacklisted” him, then Overnight is perfect proof that maybe dreams really do come true.



Directors: Paiman Kalayeh, John Lyons Murphy

Daniel Gillies’ path toward making—and funding—debut Broken Kingdom is one well-trod by any aspiring filmmaker trying to beat out a name for him or herself in the dense jungles of an industry hopelessly loyal to Hollywood gentry and practically no one else. Kingdom Come, predictably then, can be merciless in its portrayal of Gillies’ repeated stumblings, but it’s when directors Paiman Kalayeh and John Lyons Murphy incorporate interviews with well-known names, people who, despite their successes, have faced similarly suffocating obstacles, that the documentary seems to paint an altogether hopeless picture of the once encouraging dreamscape of Hollywood. Though Gillies does live to see his film finished, whether it adheres to his original vision or not hardly matters: Kingdom Come considers its very existence a miracle for which Gillies should thank the heavens.



Directors: Fax Bahr, George Hickenlooper, Eleanor Coppola

There’s no movie industry machine to fault for Francis Ford Coppola’s own personal brand of apocalypse, just the immensity of the production itself—self-financed by the director—and his relentless need to make Apocalypse Now his crowning artistic achievement. This means that Coppola’s surreal Vietnam odyssey, which reached a whopping 265 days of principal photography, was, somewhere in the director’s brilliant, anxiety-riddled mind, his definitive statement on what it took for any human being to make a massive piece of art like Apocalypse Now. The experience was, as he tells a crowd at the very beginning of the making-of doc Hearts of Darkness, not about the Vietnam War; it was the Vietnam War.

Far from an exaggeration, Hearts of Darkness spends 90 minutes defending that initial statement, and after millions of dollars, a heart attack, a number of psychological collapses, serious drug abuse, a rebellion in the Philippines, threats of suicide, and endless rewrites to John Milius’s almost-legendary script, the audience might be hard-pressed to disagree with Coppola’s assessment. In fact, one wonders—along with practically everyone involved—if Apocalypse Now was even worth the trouble, despite a respectable awards showing and suitable box-office returns. Because at the heart of all that turmoil was an impenetrable something that Coppola spent nearly a year trying to find. In the end, just like in the Joseph Conrad novel upon which the film was based, it’s hard to tell if Coppola ever found what he was looking for.



Director: Les Blank

Werner Herzog is no stranger to the ecstatic toil of movie-making, and so it comes as no surprise that one of the greatest films ever filmed about filmmaking is Les Blank’s The Burden of Dreams, a documentary ostensibly about the harrowed making of Herzog’s Fitzcarraldo in the jungles of South America, and really about, like Hearts of Darkness, what an artist is willing to do to wrench his or her vision free from the mind’s morass.

Herzog, an experimental documentarian in his own right, seems to at times toy with Blank, posturing himself as a madman on the brink of a psychotic break, unleashing one bout of intimidating crazy talk after another; years later, Blank admitted as much on his end, claiming that he fussed with the film’s vérité style, asking Herzog, for example, to repeat rants the director once shared off-camera.

Whether Herzog’s playacting or not, his horrific monologues only service the narrative Blank’s building: that sometimes an artistic vision must be seen through, no matter the cost. Whether Blank was instigating drama in the director’s reality or not, Herzog was on board: the audience must understand the seriousness of his vision. And leave it to Herzog to describe such primeval urges in Conquest of the Useless: Reflections from the Making of Fitzcarraldo, the director’s own diary-like chronicle of the production:

“A vision had seized hold of me, like the demented fury of a hound that has sunk its teeth into the leg of a deer carcass and is shaking and tugging at the downed game so frantically that the hunter gives up trying to calm him. It was the vision of a large steamship scaling a hill under its own steam, working its way up a steep slope in the jungle, while above this natural landscape, which shatters the weak and the strong with equal ferocity, soars the voice of Caruso, silencing all the pain and all the voices of the primeval forest and drowning out all birdsong. To be more precise: bird cries, for in this setting, left unfinished and abandoned by God in wrath, the birds do not sing; they shriek in pain, and confused trees tangle with one another like battling Titans, from horizon to horizon, in a steaming creation still being formed. Fog-panting and exhausted they stand in this unreal misery—and I, like a stanza in a poem written in an unknown foreign tongue, am shaken to the core.”

Just try to not imagine that in Herzog’s now infamous voice: the voice of a man at war with the wide world around him—and the voice of a man who may win.



Directors: Keith Fulton and Louis Pepe

As far as perilous movies about making perilous movies go, from Jodorowsky’s Dune to the aptly titled The Burden of Dreams, it’s no surprise that the journey of the director creating the piece of art begins to resemble, all too closely, the journey of the film’s protagonist within the piece of art itself. No less plangent is Terry Gilliam’s 2000 attempt to make The Man Who Killed Don Quixote, a kind of meta-textual reimagining of Cervantes’ iconic novel, wherein the movie’s travails, and Gilliam’s resulting failure to bring the movie back on track, characterized the director as a modern fool of sorts, a poor, delusional hero fighting windmills. Talk about an un-made movie in more ways than one: this movie un-made its director at the seams.

The chaos is caught on film by Keith Fulton and Louis Pepe, two filmmakers who’d previously been on set with Gilliam to document making-ofs for such films as Twelve Monkeys. Able to intimately capture Gilliam in the throes of almost constant defeat, watching him try to rectify one expensively mundane hiccup after another, the documentarians seem to struggle to find a single thing successful about the film’s production—and pretty much give up long before Gilliam does. Though he’s since resurrected the production and recast the parts once held by Johnny Depp and Jean Rochefort, Terry Gilliam is truly a man lost in Lost In La Mancha, a figure both whimsical and heartrending, an artist whose story lacks the depravity of Coppola’s or Herzog’s sojourns into the soul, but an artist who, so far into his massively celebrated career, was painfully reminded that adhering to one’s vision can be a job too big for even the industry’s most time-tested heroes.



Directors: Michael Epstein, Thomas Lennon

Citizen Kane is no stranger to hyperbole, and so it only makes sense that the story behind it breathes with the rigors of myth-making. In 1939, after Orson Welles negotiated an unprecedented two-film deal with RKO Pictures, he was immediately pit against an insurmountable foe: William Randolph Hearst, newspaper magnate and immensely wealthy spoilsport. The character of Charles Foster Kane was a composite of plenty of rich, white blowhards at the time, yet it was Hearst who felt most offended, to the point of trying to convince the heads of the four biggest Hollywood Studios (RKO was #5) to buy the negative of Citizen Kane in order to destroy it. If Hearst wasn’t already so far in debt, what with the building of his own Versailles-ish mega-mansion, Kane may have faced deletion, but Welles succeeded and, in the meager glow of the film’s reception—because it took decades for the film to receive the praise it now holds, high atop every human being’s best ever list—he ditched his idealistic battle with Hearst to work on his second film.

However you feel about the film that set the empirical framework for pretty much every award-winning biopic, blockbuster or historical epic that came after, its origin story is one that, as The Battle of Citizen Kane dutifully relates, had a hand in vaulting the film to the status it enjoys today. Resisting the same hyperbole that now is inescapable in talking about Citizen Kane, the documentary thankfully lets the facts do the talking themselves, chronicling the rivalry between two men who found no limits to their bluster. As a document of the excess of Hollywood influencing the excess of legend—and in essence forgetting what movie-making is all about—The Battle posits that Welles may have unwittingly, or selfishly, set the stage for the ugly industry we are just so friggin’ lucky to enjoy today.



Director: Chris Smith

In 1996, Chris Smith joined unknown Wisconsin filmmaker Mark Borchardt as the Midwesterner did everything in his power to finish a little horror film called Coven. The two-year account of Coven’s rigmarole, which Smith deigned to name American Movie, finds Borchardt, a good-hearted but estranged father of three battling his burgeoning alcoholism, obsessed with only one dream: to be a filmmaker. He sees Coven as the gateway to eventually making his real pet project, another film called Northwestern, a film whose success on which he’s seemingly hung his whole adult life. Northwestern of course, and Coven subsequently, represent so much more to Borchardt than a distant ambition or idealistic art project—instead, he’s convinced that the films are his only way to redeem himself after years of personal failings.

As we watch Smith watching Borchardt desperately keep his production going, despite lack of financing, disorganization and poor communication with a meager crew, the title of the documentary becomes ever ominous. “Making movies” in America is a vocation best left for the hardheaded dreamers, Smith implies, and Borchardt is probably out of his depth. But even when Coven inches ever closer to completion, failure is never far from the film’s purview, which leaves us with a heartbreaking question: why do we ever even participate in such a hellacious process as filmmaking? Why do we even make art at all? If the Jodorowskys and Herzogs and Coppolas of the world are the rare kinds of people so obnoxiously headstrong they can survive a process most directors would abandon, maybe they don’t have the noblest of intentions in when it comes to holding the art of filmmaking above the fray. Maybe they just have something to prove. It’s this realization that leaves American Movie so heartbreaking, and Mark Borchardt’s journey possibly the most honest entry on this list.



Director: Jon Schnepp

And now for an unmade movie about an unmade movie.

Successfully funded on Kickstarter, Jon Schnepp’s documentary about Tim Burton’s Superman Lives is, hilariously, still without a release date, a coincidence probably funny to everyone on this planet except for Jon Schnepp.

What we do know about Superman Lives is perhaps more a of a tease than Jodorowsky’s Dune: re-imagined by Burton, and written by notable geek Kevin Smith, the film cast Nicolas Cage as Clark Kent post-Doomsday-death, ratcheting up the hero’s alien qualities and re-designing the iconic blue suit. Also? Chris Rock may have played Jimmy Olsen. So there’s that.

It’s hard to say, until the documentary’s release, what ultimately killed Lives—though it’s hinted that, among obstacles like the limits of special effects technology and an unwieldy plot, the whole idea of the movie in the first place was vociferously detested by fans the world over. Yet, this was back in 1998, before Nic Cage was making at least three movies per year, each one a guaranteed test to any viewer’s gastrointestinal fortitude, so one can only imagine, with barely contained glee, what Cage could do with the material today.

It’s this speculation that makes the process of movie-making so fascinating. We witness the artistic process, from inception through execution—or lack thereof—in all its gory glory. Because it’s a process entirely bereft of the most important ingredient to any filmmaking experience: the viewer. In leaving the audience out of the process of creation, every film risks succumbing to the failure that many of the aforementioned documentaries detail: that all of these directors lost track of the destination in the midst of their journey, and so disappeared up the asshole of either the industry machine or their own all-consuming vision. If this is the case with Schnepp’s documentary, we’ll just have to wait for the movie about the unmade movie about the unmade movie of Superman Lives to find out.

Dom Sinacola is Assistant Movies Editor at Paste and a Portland-based culture writer. Since he grew up in the Detroit area, it is required by law that his favorite movie is Robocop. You can follow him on Twitter.