Colman Domingo understands how art can heal.

The day after his mother passed away in 2006, he auditioned for the rock musical “Passing Strange,” a show addressing parental loss, and it marked the beginning of his second Broadway journey.

“That production is what kept me alive,” Domingo asserts today. “It may sound intense, but that’s the reality.”

This experience partly explains why the Oscar-nominated actor felt compelled to be a part of “Sing Sing” (showing in 40 cities starting Friday, with a wider release on August 23). In this emotional new film, he plays the true story of John “Divine G” Whitfield, who wrongfully spent over 24 years in prison. While incarcerated at New York’s Sing Sing Correctional Facility in 1996, Whitfield helped establish Rehabilitation Through the Arts (RTA), a theater initiative aimed at providing inmates with essential life skills through writing and performing plays.

“I hope audiences leave with a richer appreciation for the nuanced humanity found within prison environments,” Whitfield conveys. “You’ll be astonished by the resilience of the human spirit and the potential we hold.”

Colman Domingo Embraces Vulnerability in ‘Sing Sing’

At 54, Domingo has a wealth of experience playing prominent figures, including civil rights activists like Bayard Rustin and Ralph Abernathy, and even Joe Jackson in an upcoming Michael Jackson biopic. However, “Sing Sing” presented a different challenge: He wasn’t just portraying a living person but also acting alongside a cast of formerly incarcerated individuals, many of whom had experience in Downstate Correctional Facility, where the filming took place.

“The biggest challenge was to blend in with these men; I didn’t want to appear as simply an actor,” Domingo explains. “They brought their own raw life experiences from being in institutions like Sing Sing. This significantly shaped my performance in a profound way, which makes it tough for me to watch. I feel emotionally exposed; I’ve never felt so vulnerable.”

The movie highlights Whitfield’s friendship with Clarence “Divine Eye” Maclin, who plays himself, a hesitant participant in RTA. It also showcases Whitfield’s long struggle to prove his innocence: In one poignant scene during a clemency hearing, he passionately shares how theater positively influenced his life. “Are you acting during this?” a parole officer responds skeptically, leaving him speechless.

“That line is taken directly from my parole board transcripts,” Whitfield recalls. “Colman captured my essence so accurately during that moment; I believe he could earn an Academy Award for that scene alone.”

Domingo connected with Whitfield multiple times via Zoom before filming began. He wasn’t focused on mimicking specific traits but instead aimed to embody Whitfield’s spirit—how his eyes sparkled when discussing his dance journey or how he shared his experiences at the library studying law, “helping others as well as himself find freedom.”

“I realized he is an incredibly hopeful person, still believing in the justice system—the same system that wrongly imprisoned him,” Domingo reflects. “Seeing the complexity of his character helped me understand how he navigates his surroundings and the depth of his spirit.”

For Whitfield, casting Domingo was “a dream come true,” especially as a long-time admirer of his roles in series like “Fear the Walking Dead.” He recalls feeling “starstruck” and “gushing” during their initial meeting, where their shared backgrounds and food preferences brought them closer.

“As we talked, I started to recognize our similarities,” Whitfield laughs. “I’ve always had a love for spinach, and apparently, so does he. It’s funny how those little things bring people together.”
“Don’t!”

The film instilled a sense of ‘hope’ in incarcerated individuals at Sing Sing prison

While filming in a closed prison, Domingo focused on maintaining his mental well-being through regular walks, treating himself to flowers, and involving his close friend Sean San José in the project.

“I knew I needed a companion to help me stay grounded,” Domingo, who is also a producer for the film, remarked. “It can be psychologically challenging. The layout of these places is complex; they’re built in such a way that there’s no fresh air; the cells are extremely cramped. It’s hard to comprehend how anyone could live in such conditions, regardless of their past actions. You lose your perception of space and time.”

Domingo’s compassionate and heartfelt portrayal has garnered exceptional feedback from critics, with many Oscar watchers predicting he may receive a second nomination for Best Actor following last year’s film “Rustin.” He has also been praised by Whitfield, who expressed gratitude for how he honored his story.

“Watching him felt like looking into a mirror,” says Whitfield, who was later exonerated and set free. He has since written several novels and is currently developing a screenplay, which he characterizes as an “action-adventure love story.”

For Whitfield, the highlight of this journey was presenting the film to the inmates at Sing Sing earlier this summer.

“You could see the hope lighting up their faces,” Whitfield reflected. “They now look at us and say, ‘You were right. There’s always something to look forward to.’ ”