1. American Movie (1999)

Mark Borchardt has long had a dream of making a film called Northwestern, a coming-of-age story about growing up on the rough edges of Milwaukee. He even has a plan to finance the film by first selling copies of a horror movie called Coven directly to genre fans. But getting to that stage isn't as easy as he suspects. Director Chris Smith captures Borchardt at a crucial stage in the project, as he films Coven (pronounced, per the lugubrious Borchardt's preference, "coe-ven") between bouts of binge-drinking and stints working a paper route. Borchardt's resources are limited, to say the least, but apart from a few dark nights of the soul captured by Smith's camera, he remains upbeat about the project, helped by an eccentric support system that includes his doting mother and pal Mike Schank, a slow-speaking musician sidekick who nearly steals the movie. Avoiding easy laughs without overselling Borchardt's talent, Smith's film succeeds largely because it makes audiences root for Borchardt's dream of escaping the workaday drudgery around him through art.

2. The Cruise (1998)

Timothy "Speed" Levitch is a New York City tour guide with an uncanny ability to find connections between Manhattan's architectural history and his own daily struggle to get into sync with the universal life force. Bennett Miller's The Cruise is essentially an hour and 10 minutes of Levitch at work and on the streets, delivering a long, jazzy monologue with remarkable expressiveness. At first, Levitch's nasal voice and dippy philosophizing can come off as a little grating, but he eventually wins people over with his simultaneous eagerness and melancholy, as he jumps from waxing rhapsodic about the city he loves to describing the ways it cages its residents.

3. Sick: The Life And Death Of Bob Flanagan, Supermasochist (1997)

Until the introduction of experimental treatments that have recently extended the lives of some patients, cystic fibrosis was considered a "children's disease," and an excruciating one at that, characterized by a mucus buildup in the lungs that leads to frequent infection. CF-sufferer Bob Flanagan decided to fight the disease by using pain to seize control over his rebellious body, playing the submissive to all but his affliction. Along with his partner Sheree Rose, Flanagan created short films, art installations, video diaries, and performance-art pieces around extreme acts of sadomasochism. Kirby Dick's documentary Sick doesn't shy away from his most shocking stunts, from nailing his penis to a board to absorbing a steel sphere several times larger than its intended destination. And yet the film is weirdly palatable, even inspiring, because of Flanagan's sharp sense of humor about his determination to beat the disease in his own twisted way.

4. Crumb (1995)

Terry Zwigoff's groundbreaking portrait of the sexually and racially transgressive underground cartoonist R. Crumb is a testament to how art can be a lifeline for the seemingly hopeless. Throughout the film, Zwigoff forces us to consider Robert Crumb in relation to his similarly gifted brother Charles: How did R. Crumb escape the madness and despair of his dysfunctional home life to become a thriving artist and functioning member of society, while his brother was unable to escape his upbringing and ultimately died by his own hand? For R. Crumb, the answer was to unleash his personal demons on the page, which turned out to be a more socially acceptable avenue for his dark thoughts on race, sex, and the human condition. His harshest critics demonized him for it, but in the context of Zwigoff's film, Crumb's work seems like the healthiest possible outcome for him.

5. The Devil And Daniel Johnston (2005)

Whether you believe folk musician Daniel Johnston to be a savant pop genius or a falsely idolized fringe-dweller doesn't mute the impact of The Devil And Daniel Johnston, which goes further than any documentary since Crumb in locating the intersection of madness and art. Clearly an admirer, director Jeff Feuerzeig gets intimate access to Johnston's life and reveals a manic-depressive visionary who has startled people with his peculiarly catchy pop sensibility and his terrifying periods of violence and institutionalization. His impulse to create art seems to be his salvation from total psychosis, though in the end, only his family members can handle the latter, while the hip indie musicians who initially championed him gradually recede.

6. Dancing Outlaw (1991)

Dancing Outlaw is a PBS documentary that follows Jesse "Jesco" White of Boone County, West Virginia, in his quest to have a good time, impersonate Elvis, dance, and not kill his wife. There's a fine line here between redneck-baiting and anthropological study, but Jesco is ultimately a sympathetic character. Sure, he sniffs lighter fluid and threatens bodily harm on a regular basis, but he's made human on camera, too: Jesco takes the death of his father—a famous mountain-country dancer and his inspiration—really hard, and tries to make his life better. And he hopes to get out, too: "I might get good at this dancing and come into money. I might have a whole new life, next time you see me." He did, briefly: There's a sequel to Dancing Outlaw that follows Jesco to Hollywood, where he cameos on Roseanne.

7. Project Grizzly (1996)

Troy Hurtubise was attacked by a bear once, and doesn't want to repeat the experience without evening the odds. In the years since the attack, Hurtubise has dedicated himself to constructing an increasingly complex series of bear-proof suits and heading out to the Canadian wilderness to put his science-fiction-looking contraptions to the test, all in the name of "research." What exactly he's researching, apart from his own ability to confront his fears, remains one of several questions left unanswered by Peter Lynch's wryly funny but strangely admiring film.

8. Grizzly Man (2005)

In his documentaries and features, Werner Herzog has continually turned to the ongoing struggles of man vs. the forces of nature, and he nearly always finds nature the victor. Timed as the perfect rebuke to the anthropomorphic treatment of animals in March Of The Penguins, Herzog's documentary Grizzly Man testifies to the dangers of thinking wild animals are your cuddly friends. Drawing from a wealth of video footage, Herzog follows the late Timothy Treadwell, a self-styled naturalist who spent 13 summers camping among Alaskan grizzlies in an earnest yet tragically delusional attempt to "protect" them from harm. The film becomes an open debate between Treadwell's sentimentalized view of nature and Herzog's more pragmatic take on it; the issue is settled by a hungry bear, and its "half-bored interest in food."


9. The King Of Kong (2007)

Who's the underdog here? Most fans of this funny, strange film will sympathize with Steve Wiebe, the sad-sack high-school teacher who's trying to unseat Billy Mitchell, the world-champion Donkey Kong player. But Mitchell is a strange sort of underdog in his own way—an overconfident braggart who's at best unpleasant and at worst a coward, according to the film. It's a classic good-guy-vs.-bad-guy setup, and an incredible story even for those with zero interest in competitive videogaming.

10. Danielson: A Family Movie (Or, Make A Joyful Noise Here) (2006)

Neither a performance film nor a straight documentary, J.L. Aronson's lo-fi peek into the life and music of Daniel Smith—mastermind and literal older brother of Christian indie-rock faves The Danielson Famile—takes a variety of approaches to the material, from animation to Rashomon-like retellings of Smith's origins. For more than a decade, Smith and family have staged quasi-religious theatrical "happenings" in dingy nightclubs across the country, augmenting cacophonic kitchen-sink showtunes with traces of sea chanteys, military marches, growly alt-country, wall-rattling punk, and Philip Glass-inspired minimalist pattern-making. Throughout, Smith's music and message have remained wholly his own, as he's figured out how to convert the rough-hewn DIY foundations of indie-rock into plain-speaking examinations of how hard it is to be transformed by the renewal of the mind, instead of pushed into conformity with this world.

11. Tribute (2001)

Though it's currently stuck on a shelf, Kris Curry and Rich Fox's affectionate, probing look at "tribute bands" charmed—and slightly horrified—film-festival audiences and Showtime subscribers across the country during the first half of the '00s. Following ersatz versions of Kiss, Journey, Judas Priest, Queen, and The Monkees from gig to gig and from one surprisingly contentious practice to the next, Curry and Fox raise all kinds of resonant questions about celebrity worship, the nature of "talent," and whether the best way to honor creative people is to copy what they do. Music-rights issues have kept Tribute so far underground that even its trailer is currently unavailable, but according to Curry, there may be a light at the end of the tunnel and a DVD release later this year. That would be welcome, because as a portrait of crackpot American determination, Tribute has few equals.


12. How To Draw A Bunny (2002)

The late pop artist Ray Johnson was known for his collages (often sent to friends in the form of mysterious packages), his almost paranoid reluctance to show his work publicly, and the way he maintained his Long Island home like a private art installation. John Walter and Andrew Moore's documentary about Johnson treats his life like one long performance piece, made up of shows that never came to be, collaborations that came to nothing, and a suicide every bit as odd and inexplicable as the man himself. Given how difficult it can be to find Johnson's actual art, How To Draw A Bunny is in some ways the cinematic equivalent of the museum-store catalog for the exhibits Johnson never mounted.

13. Benjamin Smoke (2000)

Anyone who spent any time hanging around the Athens/Atlanta music scene in the '90s came to know Benjamin, the fragile transvestite with the gravelly voice who worked out his obsessions with Tom Waits and Patti Smith via rambling songs about sex, drugs, and loneliness. Before Benjamin died of AIDS-related hepatitis in 1999, filmmakers Jem Cohen and Peter Sillen interviewed Benjamin in his low-rent Cabbagetown home, recording stories about his punk-rock youth and wastrel adulthood, between performances by his band Smoke. With its black-and-white photography and mournful music, Benjamin Smoke is an almost painfully sad documentary, although the fact that Cohen and Sillen have preserved Benjamin's memory mitigates some of the crushing feeling of loss.

14. Jandek On Corwood (2003)

Since 1978, a man who calls himself "Jandek" has been releasing strange little folk records full of monotone acoustic guitars and a slight bluesy howl on his own Houston label, Corwood Industries. Chad Freidrichs' documentary Jandek On Corwood looks into the mystery man's mysteries, but just a little. The film is more about the cult musician's fans, and why they channel so much devotion to a man who refuses to love them back. Freidrichs talks to underground rock critics, college-radio DJs, and indie record-store clerks, who all rhapsodize about charting Jandek's progress over 25 years via his stark album covers and the microscopic changes in his music and lyrics. As one woman says, hearing about Jandek is better than actually hearing him.

15. New York Doll (2005)

Arthur "Killer" Kane found a bit of fame with the New York Dolls, but after that band went belly-up, the music business wasn't kind to him. The terrific New York Doll picks up the story of his life at the Mormon church where he worships and works, far out of the spotlight. When a Dolls reunion is floated, Kane gathers enough money to get his instrument out of hock, and the doc follows him through the most exciting time he's had in years—never judging his religion or the fact that he's become a sweet, doddering codger while his bandmates have clung to the rock life. The film ends with a surprising tragedy that deepens its impact.

16. I Like Killing Flies (2004)

Kenny Shopsin's ambition isn't to have the biggest, nicest restaurant in New York City—it's to have his restaurant, serving his food, with his rules. In I Like Killing Flies, director Matt Mahurin—a well-known illustrator and music-video creator who's done shadowy videos for U2, Sting, R.E.M., and lots more—captures Shopsin and his family as they move their long-running restaurant from one storefront to another. Shopsin lords over his coterie of customers, treating some like family and some like pariahs. Order something from his massive menu that he doesn't feel like cooking? He'll tell you off. Try to get a table for more than four people? You'll be ejected quickly. But apparently the food—weird concoctions of Kenny's invention, most with funny names—makes his place worth a visit. The dirty kitchen seen in the film is long gone, sadly, and Shopsins now makes its home in the Essex Street Market.


17. You're Gonna Miss Me (2005)

In the mid-1960s, Roky Erickson was a groundbreaking musician at the forefront of psychedelic rock. Hard living took its toll, and arrests, mental breakdowns, deep-seated family issues, and a frightening amount of recreational and clinical drugs left the Austin rocker floridly schizophrenic, though still able to create music as powerful as it is bizarre. As You're Gonna Miss Me opens, Roky is a shambling wreck, living in hermitage with his eccentric mother and listening to eight radios and TVs simultaneously to drown out the voices in his head. But thanks to a determined intervention by his brother (and now caretaker) Sumner, a seemingly miraculous resurgence takes place, and the troubled genius finds it within himself to pick up his guitar again and go on tour for the first time in decades.

18. Driver 23/Atlas Moth (2002)

There's a fine line between dreams and obsessions, and also, as Spinal Tap put it, between clever and stupid. All four of those states are personified in Dan Cleveland, Minneapolis delivery driver by day and leader of C-tier metal band Dark Horse by night. Over the course of Driver 23 and its sequel, Atlas Moth, filmmaker Rolf Belgum chronicles Cleveland's quixotic quest for rock glory. Cleveland's unstoppable drive and single-minded focus on his band are simultaneously absurd, heroic, and pathetic—in part because he often channels that energy into foolish projects like his wildly overcomplicated (and ultimately futile) pulley system for unloading band equipment from his basement. The half-full, tiny clubs don't bother him; half the band quitting doesn't bother him; he barely seems to realize his wife is leaving him. His relentless optimism goes hand-in-hand with an obsessive-compulsive streak requiring heavy dosages of Zoloft and Prozac, and the disquieting, oddly compelling question becomes inescapable: What is the dreamer if you take away his dream?


19. Wesley Willis: The Daddy Of Rock 'N' Roll (2003)

Though Daniel Bitton's rockumentary on bizarre musician Wesley Willis isn't terribly insightful or clever, it's at least smart enough to get out of Willis' way and let the man tell his own story. The no-frills production tails a particularly feisty Willis as he goes about his everyday business: He tells countless people he's a rock star, writes lyrics barefoot in a Kinko's, urinates by a fire hydrant, rides the bus, and visits the zoo—quite an active schedule for a morbidly obese chronic schizophrenic. His friends help fill in the blanks as talking heads, explaining how Willis' medication has both improved and deteriorated his health, though much of the film's poignancy and humor comes from Willis' interactions with passersby. While visiting Chicago's Brookfield Zoo, he momentarily sulks that he's "already doomed" because he can't find a girlfriend, though he just as quickly shakes off the bleakness to harangue the gift-store staff for books so he can "write songs about bestiality."

20. Slasher (2004)

Michael Bennett, the beer-guzzling, fast-talking glorified carny at the center of John Landis' wildly entertaining documentary Slasher, is an outsider in the most literal sense. He's a man without a country, constantly leaving his beautiful wife and family so he can travel to a new city and whip the populace into a car-buying frenzy. Car dealerships all over the country fly him into their lots at great expense so he can preside over "slasher sales" where car prices are "slashed" in the most theatrical way possible, and the big prize is an unmarked car that can be had for the low, low price of $88. Alas, you get what you pay for, as the initially overjoyed, then bitterly disappointed "winners" of the $88 car soon learn. Once Bennett touches down in a new locale with his DJ/sidekick, his ambitions include selling enough cars to justify his considerable overhead, and consuming his weight in cheap beer. It's a glorious, ridiculous, faintly tragic spectacle; as one customer looking for the mythic $88 car guilelessly enthuses, "It's all very dramastic!"


21. Mayor Of The Sunset Strip (2003)

For decades, legendary KROQ DJ and tastemaker Rodney Bingenheimer was paradoxically a consummate insider who hung with all the biggest rock stars in the world (many of whom he helped introduce to American audiences), and an outsider who got a contact high from mixing with the show-business elite, even though he could never make the leap from scenester to major player himself. When George Hickenlooper started filming Bingenheimer for his funny, sad, riveting documentary The Mayor Of Sunset Strip (a nickname Sal Mineo gave Bingenheimer) his glory days were long gone, and Bingenheimer was reduced to working a graveyard shift and being usurped by one of his many former protégés. While the bands he helped break live like kings, Bingenheimer has a pauper's life in a tiny apartment cluttered with memories, ghosts, and mementos that highlight the tragic gulf between his former grand ambitions and current desperation.


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22. Stone Reader (2002)

Mark Moscowitz's Stone Reader chronicles its maker's obsessive search for Dow Mossman, a sensitive writer whose ambitious first novel, The Stones Of Summer, garnered a glowing review from The New York Times and made a deep, indelible impact on Moscowitz, but quickly slid out of print. Mossman was institutionalized shortly after the book's failure, and he dropped out of the literary world to work as a welder and a book bundler, and to care for his aged mother. Moscowitz's Slamdance-winning documentary—which climaxes poignantly with Mossman finally meeting his elusive prey—helped resuscitate interest in the author's career and prompted a reprint of Stones Of Summer, but Mossman seems likely to remain forever an outsider on the fringes, lost in his own private world of words and ideas.

23. Mr. Death: The Rise And Fall Of Fred A. Leuchter, Jr. (1999)

Director Errol Morris originally intended to add Fred Leuchter to the quartet of eccentric subjects—a wild animal trainer, a topiary gardener, a mole-rat specialist, and a robot scientist—that made up his exhilarating 1997 mélange Fast, Cheap & Out Of Control, but Leuchter's story demanded its own forum. A lonely engineer and egghead from Boston, Leuchter has made an odd living out of creating more humane execution devices, because the needless suffering inflicted by electric chairs and lethal-injection methods appalled him. But his professional interest in gas chambers segues into the far less noble business of Holocaust denial: After hooking up with Canadian neo-Nazi Ernst Zundel, Leuchter embarks on a mission to conduct experiments at Auschwitz to prove that cyanide gas wasn't used in the camp. Watching him rummaging through this sacred ground is appalling and revealing of a scientist blinded by vanity and self-delusion.

24. My Kid Could Paint That (2007)

Set aside for a moment the possibility—okay, probability—that 4-year-old painter Marla Olmstead's remarkable pieces of modern art were partially or entirely not her own. The story of the Olmsteads is really about suburban outsiders trying to break into the exclusively urban world of contemporary art, which is suspicious of artists from other circles. Both are guilty of arrogance: The urbanites for closing themselves off to work from outside their sphere of influence, and the suburbanites for holding the very notion of abstract art in contempt, as evidenced by the title of Amir Bar-Lev's documentary. The fact that Maria's paintings may, in fact, be a hoax raises fundamental questions about what art is and how it's valued by the stories of its creation.

25. The Nomi Song (2004)

The zenith of Klaus Nomi's brief, weird career was singing backup and dancing mechanically behind David Bowie on Saturday Night Live in 1979. Still, the outlandishly made-up and costumed Nomi looked somehow like Forrest Gump haplessly out of his league on the stage behind the Thin White Duke. Video footage of the SNL performance, as well as many other heart-stopping concert clips on the 2004 documentary The Nomi Song, cement Nomi's own fabricated image—that of an androgynous, alien android somehow marooned in the New York club scene during the new-wave era. Nomi, a diminutive German emigrant with an ethereal operatic tenor, rose to cult acclaim quickly in the late '70s before succumbing to bad record deals, ego, and ultimately AIDS in 1983. His few amazing minutes on the 1981 post-punk documentary Urgh! A Music War barely hint at the loneliness and strangeness of the elfin being beneath the robotic tuxedo—but The Nomi Song shows its subject to be one of the most unique, quixotic, and simultaneously ironic and innocent figures in pop-music history.