Creating Reality from Scratch

When Jill Dickerson was tasked with creating “reality programming” for the Oprah Winfrey Network, she understood they needed to bring something entirely new to the table.

Story by Lian Dolan         Photo by Shannon Cottrell

Listening to Jill Dickerson articulate the importance of telling stories that resonate with joy, humor and compassion, it’s easy to imagine her as a college professor in a media studies seminar or a social scientist on book tour. She is well prepared, knowledgeable and passionate about the topic. She speaks in complete sentences, rich in complex ideas and subordinate clauses, not the kind of snappy, industry shorthand you might expect from a busy TV executive squeezing in a meeting. Here in the library of the OWN TV headquarters in West Hollywood — which feels more like a Santa Barbara beach house than the offices of a cable network—Jill Dickerson makes you believe that reality TV really can have a higher purpose in informing, educating and shedding light on important social issues and “peeling back the layers of life’s struggles and challenges” all while being quality entertainment. Maybe it’s because she really knows her stuff. She helped to create reality TV in the 90’s and now wants to push the genre to aim higher and be more uplifting.

Dickerson is the Senior Vice President, Programming & Development at OWN TV. She joined the network in 2009 to develop a slate of non-scripted programs that reflected the kind of content that her boss Oprah Winfrey, was known for across multiple platforms. Dickerson and colleagues had to figure out where this new network fit into the Oprah landscape and who its viewers might be. “In some ways, it seems obvious because Ms. Winfrey had such a powerful brand already, but what we learned was that the TV show, the magazine, the radio channel and the website all served different audiences. They overlap but they had slightly different demos. It was a tough assignment to figure out who were we serving, ” Dickerson recalls.

After two years of hearing pitches and absorbing research before OWN TV officially launched in 2011, a brand identity emerged. “We were given a mandate to do a different kind of reality TV. The goal of the brand is to make life-changing television. To tell stories that haven’t been told before and people might not know about. To create empathy, to entertain and to show strong female characters and intergenerational families’ struggle to get through things but with joy, humor, compassion and always with love at the end. That is not what you see with other reality television.” Dickerson also notes that research shows the OWN TV audience also wants to see “a diverse representation of African- American families.”


Armed with that information, the network began to roll out shows. In Dickerson’s role at OWN TV, she’s worked on long-running hit shows like Welcome to Sweetie Pie’s, a warm, engaging docu-series featuring Miss Robbie, a former back-up singer and her family, including son Tim, out of prison and turning his life around, who create a chain of soul food restaurants. The show won two NAACP Image Awards for Best Reality Programming and, as Dickerson says, “examines the legacy of incarceration in the African-American community.” For Peete’s Sake, a docu-series that follows the life of actress Holly Robinson Peete and ex-NFL quarterback Rodney Peete, wrapped its first season this spring and included, amongst other stories, the challenges of raising a son with autism. Up next for the network is The Book of John Gray, a series featuring John Gray, associate pastor at Joel Osteen’s world-famous Lakewood Church in Houston, Texas, in a hybrid docu-series that combines scenes of family life with spiritual counseling sessions shown on camera.


That’s a wide range of stories to tell, each of which does seem to have a higher calling. Dickerson’s been hooked on good storytelling since she was young. A self –avowed soap opera fan as a teen, she went to Harvard and studied anthropology. “I have always loved stories about people from different cultures with different backgrounds.” After college, she moved to Los Angeles and spent two years working for an entertainment lawyer but didn’t feel close enough to the creative action; so back to school she went. This time, it was NYU where she received her masters in Culture & Media, studying ethnographic film. She cites Margaret Mead, anthropologist and filmmaker, as an inspiration. Her professors, like noted documentarian George Stoney encouraged her, introducing her to pioneering African-American filmmaker William Greaves. Dickerson was sure a path would emerge after graduation, though she notes, “The career that I have right now didn’t exist when I went to school.”


But her biggest career influence just may be the ground-breaking show The Real World on MTV, a docu-series focused on contemporary, young adults and issues relevant to modern life, from sex, addiction, AIDS, prejudice, sexuality, politics and substance abuse. It was fascination at first sight when Dickerson watched the inaugural season, set in New York City. Dickerson loved the social experiment aspect of the show, the mixing of backgrounds and beliefs at a vulnerable time in the participants’ lives. “It was ground-breaking, dealing with all these social issues in a new cinema verite style. They were telling important stories here. And I wanted to work on that show.”



While her fellow grad students scrambled for “the five jobs in the TV business where our degree would be useful,” Dickerson set her sights on wherever the next Real World would be set. She sent a letter to producers Mary-Ellis Bunim and Jonathan Murray of Bunim-Murray Productions stating, “I will do anything to work with you.” To her surprise, the two producers were in New York doing publicity and a meeting was set at the MTV headquarters. The next thing she knew, she was offered the job as a story editor of The Real World: Hawaii.


Dickerson would spend the next decade at working on and off for Bunim-Murray projects, including three seasons as the Senior Story Editor for The Real World. She said her time there was like “the best graduate school in the world, a meeting ground for young people, open to working outside of scripted television and, really, a group of people inventing a genre.” Her connections led to a host of other jobs, including work on signature series like The Bachelorette, Big Brother, Making The Band and The Mole. Dickerson and her team coaxed compelling storylines out thousands of hours of footage and created character-based arcs. She sums up her role, “My job was to bring direction and structure to a mass of content.”

True to her academic nature, Dickerson and her colleagues wrestled with ideas of how much to intervene, how to shape the shows safely but honestly. Dickerson’s attitude is sincere and thoughtful, understanding her responsibility as a filmmaker. She was uncomfortable when the genre shifted from real stories about real people to “lifestyle fantasy.” Maybe that’s why making the jump from the production side to the buyer side was a natural when she got a call from a former colleague about a position at OWN TV. “I really wanted to explore if we could create a different kind of reality programming.”

Starting from scratch at OWN TV was no easy task, but Dickerson is satisfied with the work the network has created. She continues to have the same interest in bringing powerful stories to the screen as she did as an undergraduate. And, after so many years in the business, Jill Dickerson has developed a leadership style that fits her mission, “I like to work with the most creative people and I like to empower them to bring their ideas at the table. What I don’t like to do is micromanage. My feeling is if you’re going to hire people who are creative, you’re hiring them because you respect their talent, their insights and their potential and it should be a collaborative process.”


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