Every once in a while, a documentary filmmaker will produce something notable – notable enough to make money at the box office, secure an Oscar nomination or a win, and turn said filmmaker into the toast of the town. Then comes the inevitable Hollywood offer: "How about directing a real movie with real actors?" Few can resist the temptation, and while sometimes it works out – e.g., Bennett Miller, Seth Gordon – more often it does not. To wit:
- CANADIAN BACON, directed by Michael Moore (1995). After his debut documentary Roger & Me made Moore famous, opportunity came a knocking. So he made a sequel. Then a short-lived TV series. Then he wrote and directed this John Candy comedy about an American president (Alan Alda) who starts a cold war with Canada. Canadian Bacon flopped hard, and Moore gave up on his Hollywood dreams – although there was that weird acting turn in Lucky Numbers...
- BOOK OF SHADOWS: BLAIR WITCH 2, directed by Joe Berlinger (2000). Berlinger and the recently deceased Bruce Sinofsky made two landmark documentaries in the 1990s: Brother's Keeper and Paradise Lost: The Child Murders at Robin Hood Hills. The latter did much to free the "West Memphis Three", heavy metal fans who were falsely convicted of "Satanic" torture and murder. Why was Berlinger – sans Sinofsky – hired to direct this quickie sequel to 1999's The Blair Witch Project, especially since it was shot like a standard horror movie? Who knows? In any event, the movie was a turkey. 15 years later, Berlinger is still a major force in the doc world; his second would-be feature, Facing the Wind, remains in development hell.
- HAVOC, directed by Barbara Kopple (2005). Along with the Maysles Brothers, Kopple was one of the first "celebrity" documentarians, thanks to a pair of Oscar-winning films about workers strikes: 1976's Harlan County U.S.A. and 1990's American Dream. The latter goosed her moribund output and Kopple released more docs, directed a handful of episodes of Homicide and Oz, and then made Havoc, her one and only feature. Despite an enviable young cast including Anne Hathaway, Joseph Gordon-Levitt, and Channing Tatum, Kopple's drama about white girls butting heads with Latino gangsters went nowhere.
- PING PONG PLAYA, directed by Jessica Yu (2007). Given the film's no-name cast of Asian Americans, you certainly can't say that this Oscar winner (for Breathing Lessons, the documentary short that would inspire the 2012 drama The Sessions) went Hollywood like Kopple and Moore. In the midst of her own second career as a TV director (Grey's Anatomy, etc.), Yu made this indie comedy about, you guessed it, ping pong. Surely a labor of love, Ping Pong Playa grossed less than $80,000 in theaters.
- ROCKET SCIENCE, directed by Jeffrey Blitz (2007). Blitz's first film was the incredibly enjoyable – and suspenseful – Spellbound, a doc about eight young competitors in the 1999 National Spelling Bee. If anyone was suited to direct a comedy about a high school speech and debate team, it would be Blitz. But Rocket Science, with its focus on a badly-stuttering protagonist (Nicholas D'Agosto), is merely enervating, despite a nice supporting turn from Anna Kendrick. Blitz made one more doc, but is otherwise directing episodic television. (Are you sensing a pattern here?)
- ALL GOOD THINGS, directed by Andrew Jarecki (2010). Now here's a guy with an odd career path: Jarecki founded Moviefone, composed the theme for the TV show Felicity, made his directorial debut with the amazing documentary Capturing the Friedmans, then helmed this art house bait starring Ryan Gosling and Kirsten Dunst. All Good Things was poorly received and made no money, so Jarecki turned his attentions to the small screen – though not directing episodic TV! Instead, he went big with the buzzworthy 2015 doc series The Jinx: The Life and Deaths of Robert Durst.
- PARTY MONSTER, directed by Fenton Bailey and Randy Barbato (2003). Bailey and Barbato are the biggest names in what could only be classified as "gay-friendly reality TV". But years before producing RuPaul's Drag Race, the two made their name directing a documentary about Michael Alig, the New York club promoter who dismembered a fellow club kid over a drug argument. The doc was called Party Monster and was released in 1998. In a twist that, frankly, you'd think would happen more often, Bailey and Barbato were then tapped to helm a feature-length dramatization of Alig's crimes, also called Party Monster, with Macaulay Culkin vamping as Alig.
- PREFONTAINE, directed by Steve James (1997). One of two sports dramas, made at the same time, about doomed Olympic runner Steve Prefontaine, this one was directed by the fellow behind the beloved documentary Hoop Dreams. James directed a couple more sports-related movies, this time for TV, but must have grown weary of being the "sports guy" and has since had a wide and prodigious documentary output, including 2014's popular Life Itself, about the late Roger Ebert.
- THE DARK WIND, directed by Errol Morris (1991). Notwithstanding Michael Moore, is there a bigger name in documentaries than Errol Morris? Every new doc by this groundbreaking filmmaker feels like an event, from The Thin Blue Line to Mr. Death to the Oscar-winning The Fog of War. But shortly after delivering A Brief History of Time, Morris was hired by Robert Redford to direct The Dark Wind, a Tony Hillerman mystery set on an Indian reservation and starring then-hot Lou Diamond Phillips. After a troubled production, Morris either quit or was fired, but he's still credited as director. We'll see if he can see his second feature, the just-announced Holland, Michigan, through to its completion – or, indeed, to its first day of production.