Matt Singletary and His Roommates

Five Los Angeles roommates turn the comedy of their lives into the first scripted YouTube show that is now in its third season


story by lisa stamos | Photo by Paolo Cascio

On a Monday morning in March, photographer Paolo Cascio and I met up at the suburban Los Angeles home of five funny, smart, and talented professional actors. At the invitation of Barrington native Matt Singletary, we had a chance to step inside their lives, and their home—where they plan and write the scripts as well as film their show, “Roommates”. It’s a new game in Hollywood these days, and these roommates aren’t waiting around for chance or luck to advance their careers.

Matt Singletary spent his early years in South Barrington before his family moved out East. He attended Grove Avenue Elementary School, and for grades 6–8, went to Immanuel Lutheran School in Palatine. He attended Saint Viator High School for the first part of his freshman year, until his family relocated to Maryland.

Singletary’s dad had a job transfer and the family moved to Baltimore. Following his father would end up being more than a geographic move for a new job. He would also play professional football after college for a few years, like his dad, before moving in a different career direction. Mike Singletary, Pro Football Hall of Fame player and coach, and Super Bowl Champion with the 1985 Chicago Bears, was hired as a linebacker coach for the Baltimore Ravens, and his son would attend the rest of his first year in high school and sophomore year in Baltimore.

Another opportunity for the coach came along with the San Francisco 49ers. The family moved to the West Coast, and Singletary attended his final two years of high school in San Jose, Calif. He went onto Baylor University (his dad’s alma mater) but didn’t stay. He transferred to California Polytechnic State University in San Luis Obispo and earned a degree in business management.

After college, the National Football League came calling, and the second-generation of the Singletary family to play football was hired by the Minnesota Vikings as an outside linebacker. His next move was to play for two Canadian Football League teams—the Hamilton Tiger-Cats, and the Saskatchewan Rough Riders. After a few years of football, Singletary moved home in 2014. “I worked as a trainer at the South Barrington Club,” Singletary says of his return to the Barrington area.

Art Imitates Life

A chance opportunity with a low-budget action movie's leading role was reminiscent of art imitating life. In the movie “Hood”, Singletary plays “RJ”, who in the movie returns home to Chicago after an 8-year tour in the army. While playing football isn’t exactly the same as being in the army (though both can be rough), Singletary’s return home followed a similar timeframe.

“It was a random move,” he says about going on an acting audition, and then being chosen for the part. “The movie role introduced me to something I never thought about doing,” Singletary says. “It was the most fun I’ve ever had.” He also had a spot in an episode of “Chicago P.D.” and realized the entertainment business was for him.

He found an agent to represent him with the goal of providing people with quality entertainment—not just to be famous. “If someone has a bad day, we [he and his roommates] want to help them shake it off. We are dudes that make people laugh,” Singletary says of the “Roommates” show.

Life Imitates Art

The five actors in "Roommates" met at the City Church in Beverly Hills and places where they worked out. They got to know each other and talked about working together to “create a dream scenario by pitching a show to the networks”. But Singletary said that that has been done before, and the group needed something more compelling. Heavily influenced by the movie “Straight Outta Compton”, the experienced actors were looking for direction, and figured that if the rap group N.W.A. could do it—five young rap artists who forever revolutionized music and pop culture and produced their own film—why couldn’t they?

Cooper Green’s parents let the actors move in with them to get a start with their vision; JT Neal had his own apartment at the time. “There were 10 people in this house,” Singletary says of the home they now live and film in. The Cooper family moved into a new house across the street so the five actors could stay where they were, under one roof, and settle in to the job ahead of creating their own show.

Becoming Script Writers

“We believed we could become writers,” Singletary said. “So before creating “Roommates” as it is now, we wrote a pilot and took it to the networks. The advice we received was to make our show shorter, push it out on YouTube, and make it about regular guys in everyday life.”

The guys decided to go for it. Their goal was to make the best content they possibly could and then look for financing or media distribution with the networks or cable along the way. The actors know what makes them laugh, and so decided to make their show called “Roommates” a reality show depicting their lives with scripted episodes that showcase a slightly more exaggerated version of themselves. “We feel led to do our show,” JT Neal said. “The work is collaborative,” Cooper Green adds. Green’s mom, Wendi, is the show’s executive producer who helps with financing, and wardrobe and set designs. “She heard the script and got behind us,” Green says. “It’s amazing what you can do on a small budget,” he adds. “My mom lets us run our own show, and offers us her input, but doesn’t make demands,” Green says. Jennifer Hook—or Miss Jen—is the team’s cinematographer, directing all the camera shots. She also plays the role of head coach for the actors.

More Than Just Friends

The show “Roommates” is about five guys and their similarities and differences. “There is some influence from the TV show “Friends,” Austin James says. “But there is no laugh track with ours. We are a dose of realism with the volume turned up.” The real-life roommates do not have a hierarchy around the show. They all make decisions together, talking it out until they find middle ground.

The key to their success is that they aren’t waiting around. They are creating their own content in the form of short episodes, filmed both at their home, and on location. They have two seasons posted on YouTube, a vehicle that some believe will bypass traditional network and cable distribution in the years ahead. One of the guest stars on Roommates, singer-songwriter Megan Nicole, debuted with YouTube in 2009 and now has 3.5 million followers. Having her on the show was a strategic move to help grow their audience.

“Roommates” is the first show to appear on YouTube that is a recurring, scripted comedy. In the first season, they use their own real-life moments to inspire their scripts with funny vignettes about life together. For season two, the “Roommates Do Stuff” writers—Neal and Singletary—wanted to pull themselves and their characters outside of their comfort zones. The cameras follow the roommates as they tackled new adventures, including drag car racing, sky diving, ice skating, and rock climbing.

Each season adds a stronger layer of experience and knowledge to “Roommates” original content, and with YouTube, the show can be seen 24/7 anywhere there is internet service. As new platforms like YouTube create greater opportunities to evolve in the entertainment business, “Roommates” is leading the way.