Few people have lived a life like Muhammad Ali’s. The certified Greatest of All Time has had umpteen books, documentaries, and biographical dramas that tell and retell his years as a heavyweight champion and a political activist. Hell, there is a movie about Muhammad Ali, starring Muhammad Ali. (Not to mention an iconic Esquire cover featuring the legend.) But a new Prime Video series, simply titled The Greatest, aims to be more than another boxing biography. The Greatest isn’t just about the man who was born Cassius Clay, but the family who raised him into a legend.
“Most things you’ve seen or read, they don’t go into his childhood much,” says Lonnie Ali, the 86-year-old fourth wife of Ali, in an interview with Esquire. “The Greatest is his pathway to growth, at home with his brother and his parents. It’s a granular deep dive into Muhammad’s life, to understand who he was, how he started, and how he progressed to become one of the most beloved icons.”
Created by Ben Watkins, with Lonnie Ali among its executive producers, The Greatest stars newcomer Jaalen Best as Muhammad Ali in the years spanning his gold-medal victory at the 1960 Olympics in Rome to his championship bout against Sonny Liston in February 1964. Between these hard-fought wins, Ali lives in Louisville—where his godlike status collides with Jim Crow—and trains to turn pro with the support and tough love of his family: father Cassius Clay Sr. (Omari Hardwick), mother Odessa “Bird” Clay (Dana Gourrier), and brother Rudy, later Rahaman Ali (Kai Parham). The series will begin streaming on Prime Video on November 4.
You can watch the trailer below, along with exclusive images only at Esquire.
In conversations with Esquire, Watkins and the stars describe the series as a coming-of-age family drama that so happens to follow the footsteps of an icon. That meant putting an equally big spotlight on the people who surrounded Ali in his most formative years—and being truthful to who they were. “It’s an interpretation of real life and a real person,” says Watkins, who adds that there was a “feeling-out period” where he sought to gain the trust of Lonnie Ali and the Ali family.
“I had to gain their trust, but they also had to give me leeway to tell the story the real way. That means you’re going to see parts of Muhammad Ali that aren’t always flattering. And it shouldn’t be. We shouldn’t do something where he’s perfect.”
At the same time, Watkins and his team knew they were treading familiar ground. Throw a rock at your Roku and you’ll hit a documentary about Ali. And his mythical boxing matches? They’re on YouTube, upscaled to 4K. So Watkins, whose previous work in television includes Burn Notice and Cross, imposed a rule (albeit loosely) for his writers’ room. “The rule was: Anything that’s in a documentary will not be in the show,” he says. He admits it’s an exaggerated rule—so much of Ali’s legend unfolded in the public eye—but it was about setting “intention.”
“We need to be excavating, looking for details that give us a better understanding of who this is. The Crown is a recent example, where some of the best episodes are about things no one ever knew about. That’s what I wanted to do.”
Jaalen Best stars as Muhammad Ali in The Greatest, along with Dana Gourrier (left) as Odessa, Kai Parham (center-right) as Rudy, and Omari Hardwick (right) as Cassius Clay Sr.
Jaalen Best had not boxed before he was cast as Muhammad Ali. He trained extensively for months, and shed 20 pounds to achieve the look of a young Ali.
Which is what made Ali’s family compelling subjects for a streaming series. You can quiz sports scholars and historians on Ali’s stats or what his conscientious objection meant to the anti–Vietnam War movement and to future athletes to use their platforms for protest. But ask them about Ali’s family—the way he doted on his mother, the way his father built dollhouses as a hobby—you might stump them all.
“That’s what you see here,” says Omari Hardwick, who plays Cassius Clay Sr. in The Greatest. “You get to see how the person we know as Muhammad Ali is created. How is he able to think the way he thinks? Who are the folks around him who shaped his thoughts? The backdrop is the boxing, the things we know that we don’t have to read about. The forefront of this story is the family members around him.”
Lest you think The Greatest is all feel-good warmth, think again. Set against the segregated South, the home life of the Clays was as turbulent as it was supportive of his lofty ambitions. Resentment, greed, suspicion, and infidelity sit at the same dinner table as love and compassion. “The reality is you could never be as powerful as Muhammad Ali if your greatest opponent was not your father,” adds Hardwick.
But the main event of The Greatest is still bearing witness to the rise of Ali’s legend. Jaalen Best, in his first-ever lead role, stars as the young champ when he still went by Cassius Clay. Best tells Esquire that he studied other onscreen Alis—namely Eli Goree in Regina King’s One Night in Miami—before figuring out his own voice through repeat listens of Ali’s real interviews. “I would watch these again and again, and I would find the little pieces that I think I could change,” he says. “Listening to his voice constantly, and repeating it so many times until I felt like I can do a voice memo [in his voice]. It was repetition, repetition, repetition.”
An athlete before he became an actor, Jaalen Best says he could never get enough playing time to show off his stuff. “I could never showcase how great I knew what my potential was,” he says. “Taking this opportunity, I was like, ‘I’m gonna show y’all how great I am.’ Proving to myself how great I could be, proving to people how great I could be, while also bringing to life the greatest Muhammad Ali—”
Best catches himself. “That was a rhyme. I didn’t even try to rhyme.”
Dana Gourrier describes Odessa Clay, Ali’s mother, as a “compassionate” and “loving” figure. “She’d seen someone get killed in the ring. So she’s bringing that wisdom into the relationship with her son,” she tells Esquire. “Sometimes with your kids, you gotta back up and let them go.”
Omari Hardwick, who plays Ali’s father, says The Greatest is about learning “more about the man who made the man.” “About the woman who made the man, the brother who made the man, and therefore being able to understand the man better.”
Oddly enough, learning how to box was the easier part. “I remember getting the role in April 2024. When I met with the trainer, the goal was [to train] from June all the way until we went to film the next year. So for eight months, I had to run every single day, Sundays off. I would report that time in and weigh myself every morning.”
Though a natural athlete, Best had never boxed before. Quite literally, he had to be shown the ropes. “[My trainer] would be like, ‘This is the proper way to throw a hook,’ because if you can understand the proper way, then you can understand how Ali broke the laws to create his own.”
Adds Best, “We would do three hours training doing the Ali routine. He’s putting me in the ring—I’m dancing around, throwing punches. At night he would send me clips of Ali and he’d say, ‘Break this down for me, punch by punch.’ That’s how I started learning the way he floats, his shoulder relaxation, how natural his face was. In that routine of studying it, it allowed me to really bring it to life.”
Michael Ealy stars as Malcolm X, a close friend and spiritual mentor to Muhammad Ali, at least during the years encompassing the first season of The Greatest.
For as much as the team strove to tell Ali’s story from a new angle, The Greatest inevitably comes across some of his greatest hits. Like his climactic battle with Sonny Liston (played in the series by Amin Joseph). Other moments are still up in the air in potential future seasons. Ben Watkins tells Esquire he has a three-season plan in mind. This first season, which he’s titled “I Shook Up the World,” is all about Cassius Clay becoming Muhammad Ali. Should the series see a renewal for season 2, it would be titled “I’m Ready to Die,” covering Ali’s ban from professional boxing due to his refusal of induction into the Vietnam War.
As for season 3? It’s called “I Am the Greatest.” “It takes place in the mid-’70s. Of course it includes Rumble in the Jungle,” Watkins says. When I ask if it would also include his infamous (and disastrous) match against Japanese pro wrestler Antonio Inoki, Watkins says it might. “I would love for folks to see that wrestling match, because not only does it make a huge statement about how the world was at the time, but he [Ali] sustained injuries that he never really recovered from.”
Sadly, Watkins skips Ali’s legendary meeting with the Beatles entirely, which took place weeks before his fight against Liston in 1964. “Imagine the challenge we have in terms of casting,” he says, “You have to get four legends right. I had to, unfortunately, let that moment go.”
But The Greatest isn’t about recreating episodes of Ali’s life in period-accurate cosplay. It is about how one man changed the world with his people at ringside. “Before he was a legend, he was a man, a brother, a father, a son,” says Watkins. “We admire him for accomplishing things that are almost superhuman, and it’s easy to forget he had the same fears and flaws. Once you are reminded that he’s human, you admire what he did even more, because you know how hard that is to do.”