Third Time's the Charm

Documentary filmmaker Caroline Waterlow ’91 is best known for her film OJ: Made in America, which won the Oscar for Best Documentary Feature in 2017.


When CAROLINE WATERLOW ’91 took the Hard Auditorium stage earlier this month, the moment had been a long time coming. Waterlow, who was originally slated to speak as Pomfret's 2019 Lasell Visiting Alumna was unable to attend after a family member became ill. In the spring of 2020, she was again scheduled to speak, right when Covid was first hitting Connecticut. "Third time's the charm," she joked.

An award-winning producer, Waterlow is best known for her film OJ: Made in America, which took home the Oscar for Best Documentary Feature in 2017. “Our culture will celebrate certain values at one time, and then later, through the lens of a different generation, will question what it was told, and why it was important. Our country is going through a reckoning, and the storytelling we see right now is trying to reflect that.”

When O.J. premiered at the Sundance Film Festival in 2016, it immediately struck a nerve with critics, garnering Oscar buzz wherever it went. Writing in the New York Times, film critic A.O. Scott called the documentary a feat of tireless research, dogged interviewing, and skillful editing. “Some of the images have an uncanny familiarity,” he wrote, “while others land with almost revelatory force.”

Part character study, part social history, Made in America follows Simpson from his early days as a star running back in the NFL into the tawdry, media-obsessed trial that captured the country’s attention in the 1990s, before finally turning to the Nevada prison where he served nine years of a thirty year sentence for robbery and kidnapping. 

Spanning a half century, the film also explores the racial tension, civil unrest, fractured media landscape, and fraught celebrity culture that continues to define the American experience more than twenty years after the original verdict was handed down, one that signaled a deep and growing divide between white and black communities.

“There are benefits to revisiting stories with the passage of time,” Waterlow says, “which is why retelling stories for different generations is an important thing. Now we can see the context and all the connections and repeated patterns; maybe it was all too close in 1995.”

Waterlow speaks with students in Parsons Lodge.

A Montreal native, Waterlow graduated from Pomfret in 1991. During her time on the Hilltop, she earned a reputation as a distinguished thespian who took home the drama award in her senior year. In 2008, she returned to Pomfret for Career Day, telling students, “Knowing what you don’t want to do is as important as knowing what you do.” Since graduating, Waterlow has served as a class secretary and is a current member of the Alumni Association Executive Council. In  2011, the Pomfret Alumni Association gave her an achievement medal, one of the highest honors the School can bestow upon a member of the alumni body.

After leaving the Hilltop, Waterlow deferred college for a year to attend the British American Drama Academy in London. She graduated from Emory University in 1996, and eventually settled in New York City. Her first big break came in 1997 when she was hired by Kunhardt Productions to work on The American President, a ten-hour series for PBS, chronicling the history of the American presidency, which premiered at the White House in 2000. 

In addition to Made in America, Waterlow’s film credits include Cutie and the Boxer; Supermensch: The Legend of Shep Gordon; and Brooklyn Dodgers: The Ghosts of Flatbush, which earned her an Emmy Award in 2008. Her newest film, Qualified, chronicles the mercurial rise and rapid decline of Janet Guthrie, the first woman to qualify for the Indy 500. 

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