The actor, who first came to fame as football player Ricky Baker in the groundbreaking 1991 film, "Boyz n the Hood," barely looks to have aged since then.
Chestnut now stars in a new NBC drama, "The Enemy Within," a psychological thriller which teams him with actress Jennifer Carpenter.
In the series, Erica Shepherd (played Carpenter) is a brilliant former CIA operative turned traitor serving a life sentence in a Supermax prison.
Chestnut's character, FBI Agent Will Keaton, enlists Shepherd to help track down a fiercely dangerous and elusive criminal she knows all too well.
While the concept may sound familiar, Chestnut told CNN it's not what viewers are used to seeing on the small screen.
"People may have made similar comparisons to other shows, but our show's different because I'm in the FBI, she's in the CIA, but that's just the backdrop of the show," he said. "It's a character-driven show. We're driven by emotion ... there's emotional push and pull throughout each episode."
The role is different from Chestnut's previous portrayal of pathologist Beaumont Rosewood, Jr. on Fox's "Rosewood," which Chestnut said he also loved.
"It's a cable feel on network," he said of "The Enemy Within." "And that's what really intrigued me about it."
Playing Will Keaton is also more dramatically and physically intense.
Chestnut, who turned 50 on New Year's Day, stays in shape with the help of his trainer, Obi Obadike.
The pair co-authored a fitness book and launched a New Year's resolution challenge to help others get fit.
Obadike said it's been great to work with Chestnut.
"First and foremost we're great friends," Obadike said. "That friendship turned into a bond after helping him get in shape. It's been phenomenal."
Chestnut has brought that spirit of wanting to be his best to his career as well.
He said he's seen Hollywood open up more opportunities for actors like him.
"When I came up, I think really the only black male lead was Denzel Washington," Chestnut said. "Right before we came out with 'Boyz n the Hood,' Wesley Snipes was in 'New Jack City.' But now I'm looking at everybody. There's Samuel Jackson, Denzel, Idris Elba, Michael B. Jordan. There's a lot of people out there now."
Chestnut said he's also seen more inclusive storytelling on television, with more black men in lead roles.
Such representation helped "The Best Man" become part of a cannon of beloved black films.
The romantic comedy about a group of friends who come together for a wedding was so popular that fans lobbied for years before a sequel, "The Best Man Holiday," was released in 2013.
Chestnut said he's anxious to do a follow up film.
"There's a script for it," he said.
So what's the hold up?
"Studio red tape," Chestnut said. "Just getting them to give it the green light."
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