daydreaming

DAYDREAMING WITH FILMMAKER, MADISON O’LEARY

In 2017, Black Memorabilia premiered at the Museum of Modern Art (MoMA), and subsequently aired on PBS, gaining mass acclaim within the independent documentary circuit. If you’ve seen it, revered filmmaker Chico Colvard likely comes to mind. However, the narrative voice – and a major force behind the collaborative project – was a quiet Boston girl named Madison O’Leary.

Since the success of Black Memorabilia, Madison has gone on to carve out a name for herself as a producer for C-Line Films. She’s worked with major platforms, such as HBO, Netflix, and MTV, using art to raise public awareness of issues plaguing our nation.

The News Station spoke with her in an exclusive interview where we discussed life, art, and social justice. 

Madison informed us, it all started for her with daydreaming.

“I’ve always been a daydreamer,” she tells TNS, “and I’ve always spent a lot of time in my imagination. Film and television are the realized version of that.”

Born in 1991, Madison grew up with two moms and an older brother. 

“I had the most loving childhood. We were the first wave of lesbians, so that was a defining part of my life,” she recounts. “It made me understand certain aspects of life early on. It gave me a real understanding of oppression and the expectation of the world.”

Homeschooled for the first portion of her life, there was no TV in Madison’s house. Part of this, she explains, was financial. The rest was because her mothers didn’t approve of television.

It wasn’t until high school when she finally entered into the public education system, where she acquired an even deeper understanding of how unbalanced society is. 

“I was the only white girl in my class,” Madison remembers, “so I saw how drastically different the world treated me than my classmates. How they were picked last for everything, including internships. Seeing that racial inequality from such an early age definitely shaped me a lot.”

She remembers feeling the injustice, especially one particularly vivid incident. 

“There was this random middle-aged white man who would hang out at my school being creepy toward the girls. One day, this guy named Joe – who’s Latino – put his hand up, and told him he had to leave, and the man slashed Joe’s face,” Madison recounts. “When the cops showed up, they arrested Joe.”

It was during these youthful years that Madison – finally able to indulge in visual media – discovered her deep, almost innate, interest in film. In a stroke of serendipitous luck, her humanities teacher was none other than her future collaborator, Chico Colvard.

“He taught me a lot about social justice,” Madison recounts, “and how we perceive the world and how the world perceives us.”

While still a teen Madison sensed the American Justice System was little more than a trap, strategically enslaving people from the most disenfranchised factions of society. She knew, after decades of U.S. officials of all stripes normalizing mass incarceration, the  public perception of both the system and those locked inside needed to be altered.

“I remember thinking about the idea of the Holocaust and thinking, ‘what would you have done if you were there?’ For me, our Holocaust was the carceral system,” she says. “It’s one of the greatest genocides happening in America.”

The question of “what would you have done?” wasn’t just a table topic for Madison. While dreams of making films were already brewing, so was an obligation to social justice. But she struggled conceptualizing a world where she could do both.

After high school, she earned a degree from the University of Massachusetts. Then at 22 she was hired to work at a pre-release center in Chicago. For six months Madison prepared incarcerated individuals to reintegrate with society. 

While there, everything she suspected about the so-called justice system was reaffirmed.

“I met a man that was caught with some weed when he was 17 or 18 and got a 40-year sentence. He was just a wonderful human, and he was finally getting out,” Madison recalls. “Another man got a two-and-a-half-year sentence, and he had molested five kids under the age of nine.”

This was, and is, the American ‘justice’ system. 

“He was very wealthy, and there was no remorse with this man,” Madison remembers. “He had just gotten away with it.”

Following her job in Chicago, she lived in New York briefly. Then Madison moved back to her hometown. 

She spent the next three years working fulltime as a trauma and abuse counselor in the Framingham Correctional Facility for Women – just 30 minutes (in great traffic…) west of downtown Boston. 

Many of her clients there had endured sexual and physical violence at the hands of men. The Correctional Officers – or COs – and the rules themselves seemed designed to only make the pain and trauma worse. 

“What I was asked to do by the company I was working for was so dehumanizing,” she claims. “If you were meeting one-on-one with a client and they started crying, you had to call in a CO, and most of the CO’s there were male. I refused to do that.”

Around this time Chico Colvard was making waves in the independent film industry. His project, A Family Affair, became the first film acquired by Chicago-transplant Oprah Winfrey when she started the Oprah Winfrey Network (OWN). Seeing her old humanities teacher use visual media to address the very issues that led her into correctional facilities, Madison decided to make a move herself.

“At that point,” she says, “no matter my intentions, I realized I was part of a system I didn’t believe in. I wasn’t changing it or fighting for prison abolition. I tried to tackle how to accomplish it as a single person with no political power, so it brought me back to film.”

In 2017, she was hired by C-Line Films – an (in)dependent storytelling group committed to social justice documentaries. 

Madison on Black Memorabilia, then spent the past five years continuing her fight for a better society, while also solidifying her name and reputation in the world of film. She’s made three documentaries to date and has three more in production—including a piece for MTV.

In 2020, she founded the Prison Reform Initiative (PRI), an organization aimed at using the arts to abolish the American prison system as we know it. 

With Emmy-nominated actor, Richard Cabral (The Mayans) and bestselling author and activist, Marlon Peterson (Bird Uncaged) as Executive Producers, PRI is currently working on Collapsing the House – a series set to expose the inhumanity of mass incarceration through intimate narrative portraiture pieces of artists and activists behind bars.

“We often ignore what we cannot face,” she says. “We hide from the truths that we cannot accept and prison is a prime example of this.”

Each episode of Collapsing the House will explore the life story of an incarcerated artist, using a poetic and lyrical approach, while prioritizing humane treatment and prison abolition. The series will move through Gregory Stanton’s Ten Stages of Genocide, starting with the first, “Classification,” and ending with the last, “Denial.”

The quietest voice in the room is the one most worth listening to, at least in Madison’s case. She’s dedicated her life to fighting for the oppressed. She’s now a force, both as an artist and activist. 

Madison’s story, if nothing else, should move us to consider a society in which we all took the time to entertain our daydreams.

Michael J. Moore is a writer and journalist.  He's received awards for his work and been highlighted on television. He's written for various anthologies, journals, newspapers (including HuffPost) and magazines, and has been adapted for theater. His full bio is here.

Michael J. Moore is a writer and journalist.  He's received awards for his work and been highlighted on television. He's written for various anthologies, journals, newspapers (including HuffPost) and magazines, and has been adapted for theater. His full bio is here.

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