Around him is a crew, tirelessly working to recreate 1900s New York. Soderbergh, a meticulous but expedient filmmaker, is commanding his team for the Clive Owen-led series. Holland marvels at the symphony from afar, waiting for someone to say action. “That whole experience was incredible,” Holland tells Playboy. “Working with somebody on Steven’s level whet my appetite, you know?”

Eventually, his number is called on set, and he does what he’s meant do: act. As Dr. Algernon Edwards, Holland wholly embodied a man forced to battle prejudice in the Knickerbocker Hospital. It was a star-making turn. It’s also the experience that propelled Holland into confronting a similarly racial issue in his own life. “The role made me believe I was capable of being more than just a black friend,” he says. “That was a lot of what I was seeing in the parts that were peripheral.”

This light-bulb moment of self-worth carried him into Barry Jenkins’ Moonlight, where he plays a black friend, not the black friend, to Trevante Rhodes’ protagonist, Black. The images of Holland are vivid. In a diner, wearing a short-sleeved white shirt, smiling wide as Barbara Lewis’ “Hello Stranger” plays on a worn jukebox, Holland is unmistakably captivating. His eyes project a melange of trepidation and adoration.

Holland brings that same striking charisma to the Netflix film High Flying Bird, a collaboration with Soderbergh that “came out of a place frustration around not having the parts I wanted and not getting access to the parts that I was hoping to play.” Penned by renowned playwright (and Moonlight cowriter) Tarell Alvin McCraney and costarring Zazie Beetz, Holland plays an NBA sports agent in the midst of a lockout. In preparation for the role of Ray Burke, the 39-year-old actor spoke to agents around the league. “I had imagined that it was a business relationship, you know? That it was friendly, but business first,” he says. “But they’re highly involved in their [clients'] lives, in every aspect of their lives. And with their families as well. It’s not just a bunch of sharks trying to take advantage of these young guys. A lot of them really, really care.”

Holland fostered a similar mentor relationship with Soderbergh. “He immediately opened this door in that way,” he says. After long days on the set of The Knick, Soderbergh would extend an invitation. “He said, ‘Look, man, why don’t you come over, we can pick a film, we can go through it and we could break down shot by shot and discuss why this shot and not that one, why they edited it this way and not that way?’” Naturally, Holland jumped at the opportunity.

In these late-night film-studies sessions, Soderbergh imparted wisdom accumulated through 30-plus years of moviemaking. “He taught me to be good to the people that you work with, and not just the people that you work with immediately, but to everybody involved in the process,” Holland recounts. “He always said managing expectations is important. And then the last thing: error-correction. By that, I think he means it’s OK to make mistakes, but don’t keep making the same mistakes.”

When I ask Holland what mistakes he’s made in his career, he’s forthright. “It’s tough. When it comes to making choices about projects to get involved in … there are times when I chose to do things for the wrong reasons because I thought it would lead to something else, or I thought it would be a smart thing to do,” he says. Holland is capable of introspection while still looking ahead. “From now on, what I’m committed to is only doing things that truly speak to me,” he explains. “And if they don’t, I’m not going to be seduced by all the other reasons that you can come up with for doing the thing.”

And then there are the missteps we make as a result of work. Since building a career in his 20s, both in TV and film, Holland has been routinely ambitious. “To a fault at times,” he admits. “It kept me from being as present as I should have been. There were people in my life who were very important to me, and because I didn’t have balance, those relationships suffered in a way that they shouldn’t have.” There’s a pause. You can hear the sincerity in Holland’s voice as he reflects on his youthful inclination to place work before all else. “It has been hard to look back at those decisions that I made and accept the consequences of those decisions.”

The past may inform the present, but it can’t hold us captive. In 2019, Holland bangs his drum to a different beat. “Now I feel like living a life that feels full and exciting, where I can really engage with the world, and building meaningful relationships with people.”

One of those relationships is with Oscar-winning actor Mark Rylance. This past summer, Holland costarred alongside Rylance in a London production of Othello. But the memory that lingers is one at the intersection of work and family—“a tough balancing act,” as Holland notes. On Oct. 13, closing night of the show, Holland’s parents flew in from Ala. As the program concluded, Rylance walked onstage and spoke fondly of his costar. In the middle gallery, Holland could see his mother and father wiping away the tears. “It just felt really lovely, you know?” he says. “All the difficulties that came with playing that part suddenly felt worth it.”

It was the kind of moment one spends a lifetime searching and longing for—to feel, at once, validated and reborn by the people that brought you here. “My mother and my father are brilliant, brilliant people. My mom is probably the smartest person I’ve ever met, and my dad is a poet at heart,” he says. Once Holland finds his rhythm, it unspools like an impromptu Shakespearean monologue. “And yet they were born in a place and in a time when there were very real restrictions on what they were able to do and how far they were able to go.”

He continues of his Ala. upbringing, “Growing up where I grew up, I’ve always felt this responsibility to somehow live the life that maybe they didn’t have access to. In that moment, it felt like a relief that we, together, had arrived at that place, you know? It felt like a release.”

The publicists are telling us that our time is coming to an end, but Holland has more to say. “I think all of this is connected to the idea of finding balance. The moment released me from that obligation of feeling like I had to live out their dreams.”

There’s a beat. “You know what I mean?” We do.