"I might have a whole new life, next time you see me": 25 worthwhile documentaries about ambitious outsiders

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."

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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.

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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.