Before decamping for Los Angeles, actor Rome Flynn spent his childhood across all sides of Chicago, splashing in open fire hydrants and playing tag in the hallways of apartment buildings. He entertained his mother and siblings for hours with impressions of Denzel Washington, Will Smith, and Jamie Foxx — glimmers of things to come.

Today, Flynn is a familiar face to millions, performing alongside Viola Davis as law student Gabriel Maddox on ABC's primetime drama How to Get Away with Murder. He's also won a daytime Emmy for his recurring role on The Bold and the Beautiful.

But Flynn’s path to stardom has been anything but straightforward. His family spent months in and out of shelters and public housing, including the Henry Horner and Robert Taylor Homes, and occasionally lived out of their car. He recalls one of several Christmases spent at a Salvation Army shelter on the North Side, when a man dressed as Santa Claus let him and his siblings pick toys from his sack.

“I didn’t have the privilege of believing in Santa Claus,” Flynn says. “Growing up in that way, in that environment, you were just trying to figure it out the whole time.”

By the third grade, he’d lost a friend to gang violence. Later, he watched through his apartment window as a neighbor he admired was shot.

“I had to understand the concept of death pretty young,” Flynn says. “I think that’s partially the reason I’ve found myself successful: I realized at a young age that life is short.”

Flynn (right) and his family in an undated photo taken at the lakeshore
Image: Courtesy of Rome Flynn

Flynn funneled his early energies into basketball. His family eventually moved downstate to Springfield, where he graduated from Lanphier High School. A hand injury prevented him from participating in traditional recruitment, so he attended open gyms at nearby colleges, mostly uninvited, until he secured a basketball scholarship to Benedictine College.

From there, Flynn had a set plan: He would play on the team and study psychology or nursing. But before he started his first semester, he heard a casting call for models and actors on the radio. A friend dared him to go and, despite having no formal training in the arts, Flynn accepted. He was floored when he received the call telling him he made it to the next round. “It was scary as hell. I don’t get scared, ever, so it intrigued me,” he says.

Flynn took the leap. He turned down the basketball scholarship and began booking small gigs in Chicago, including work on Columbia College students' thesis films and commercials, with a goal of someday moving to Los Angeles.

There were some brief setbacks. He struggled to save up for the move, working as a seasonal janitor at the Illinois State Fair, pawnbroker, and door-to-door insurance salesman at different times to make ends meet. At one point, he relocated to Peoria to live with his dad. Then, a few weeks before he was slated to go to California, he hit another car while driving and fled the scene. Rather than delay his cross-country move further, Flynn chose a five-day stint in prison over probation.

At Peoria County Jail, he watched his first soap operas, including the CBS daytime drama, The Bold and the Beautiful. He regaled his fellow inmates with his plans to move to L.A. to be a star. They laughed and called him Ken — like the Barbie doll — but Flynn’s faith didn’t shake.

When he finally arrived to California, success wasn’t immediate. For a time, he rode a longboard to restaurant and department store jobs and countless auditions until he scored a role in the television movie, Drumline: A New Beat. From there, he spent more than two years on The Bold and the Beautiful — the same show he watched in prison — as the grown-up Zende Forrester, a fashion intern who first appeared on the series from 2001 to 2002 as a young orphan.

Flynn later worked with Tyler Perry, one of his childhood heroes, on the OWN show The Have and the Have Nots and A Madea Family Funeral. But it wasn’t until he booked a role on How to Get Away with Murder as law student Gabriel Maddox that he started believing his journey to the screen hadn’t just been luck. He initially appeared in the season four finale, which aired in March 2018; when he got the call that the show wanted to extend his role to a season regular, he cried.

“To get a job on a huge network like ABC and to be working alongside Viola Davis — I realized this is what I was meant to do,” Flynn says. “Booking that show, it changed my life.”

Some of Maddox’s traits, including the character’s affinity for basketball, were written with Flynn in mind. “I really like [Maddox’s] honesty and his ambition to be a champion for people,” Flynn said. “He’s a prison abolitionist, which is very courageous.”

With the last season of the show airing on Thursday, Flynn says it sometimes still feels surreal that he’s come this far. “I feel like I’ve lived a lot of different lives,” he says. “When I look back to when I was in Chicago — or in Springfield, or Peoria — I feel like they’re different people. They have the same values, but they talk differently, dress differently, have different interests.”

Recently, he found a notebook filled with goals from when he first moved to L.A., before booking anything: Win an Emmy, be a series regular on a show, book a film, pay rent this month, keep up with car payments, to name a few. He’s accomplished most of them.

“But there’s so much I still want,” Flynn says. “I don’t think I’ll ever really arrive.”

The final season of How to Get Away with Murder airs on ABC from April 2 to May 14.