To save repetition, let's just stipulate that "shocking" describes every true-crime movie on this list.
Lots of excellent documentaries examine crimes — "The Times of Harvey Milk" climaxes with a murder and little-girl-becomes-art-superstar charmer "My Kid Could Paint That" may involve fraud — but, in my mind, a true-crime doc only pops if the crime itself is front and center. The Holocaust was criminal, for instance, but the many fine nonfiction films about it belong to a different category.
As shown in HBO's current true-crime series, "I'll Be Gone in the Dark," these are the kinds of stories that lead to obsessively tweeting about "Tiger King" (I have not seen it but, in any case, I'm only including feature films) or, in pre-social media days, jamming message boards with theories about the unbelievably twisty murder investigation of "The Staircase" (whose director made a previous, even better, movie you'll find on the list below).
Given our fascination with crime, there's no surprise it features in so many nonfiction films, but it is surprising it took Hollywood so long to take notice. Academy Awards have been handed out for documentary features since 1942 but no true-crime doc won until six decades later ("Murder on a Sunday Morning"). Trophies almost always went to World War II-themed documentaries before Oscar shifted its attention to nature films and then biographies, including 1957 winner "Albert Schweitzer," by St. Paul native Jerome Hill.
In keeping with an organization that has usually favored safety over risk, Oscar docs avoided controversy until the anti-Vietnam film "Hearts and Minds" won in 1974. An inspiring portrait continues to be the clearest path to awards — think of Muhammad Ali in "When We Were Kings" or last year's daredevil mountain climbers in "Free Solo" — but Oscar has begun to reward compelling filmmaking, not just compelling topics.
After years of pushback because of his use of dramatizations, Errol Morris finally won in 2003 for "The Fog of War." In the aftermath, documentaries have become even more open to experiments that get at deeper truths. It's exhilarating to see documentarians explore the possibilities of animation ("Waltz With Bashir"), re-enactments of events that weren't captured on film ("Man on Wire"), surreal storytelling ("The Act of Killing"), autobiography ("Faces Places") and personal essay ("Minding the Gap").
Those experiments demonstrate that there's no limit to what a documentary can do. These true-crime titles demonstrate there's also no limit to the peculiarity of the human experience.
Dear Zachary (2008)
Warning: It's a gut punch. Director Kurt Kuenne originally intended the film, which can be seen in its entirety on YouTube, for an audience of one: a baby named Zachary who never knew his dad, Andrew. He was murdered by Zachary's mother, who fled to Canada, launching a jaw-dropping sequence of events that ended in unimaginable tragedy and, ultimately, new Canadian laws.