Nearly 50 years after he talked his mother into parking outside Muhammad Ali's Chicago mansion, Ben Watkins has finally gotten closer to his childhood hero. Watkins is the creator and showrunner of The Greatest, Prime Video's planned three-season drama about the boxing legend, which released its complete eight-episode first season on Nov. 4.
Watkins traces his fascination to a children's biography he ordered from the Scholastic catalog in first grade. Not yet ten years old and newly moved to the Illinois suburbs in the late 1970s, he learned Ali lived nearby and persuaded his mother to drive him to a wealthy enclave on Chicago's south side, where they sat outside Ali's Tudor mansion for an hour. When a limousine with tinted windows finally pulled out, his mother told him Ali had waved. "I didn't see him at all, but in my little kid mind, I was like, 'I just met Muhammad Ali,'" Watkins recalled in an interview with The Hollywood Reporter. "And that was it for the rest of my life."
That lifelong attachment shaped his ground rules for the series. "I didn't want to do a traditional biopic, so I started the writer's room by saying, 'If it's been in a documentary, it can't be in this show,'" Watkins said, adding that he wanted a character study viewers would watch even without the famous fights and historical milestones.
The project first reached Watkins through his agents, and he said the major lure was that Ali's widow, Lonnie Ali, and the estate were behind it. He initially passed, only for the show to come back across his desk years later after Michael B. Jordan and Outlier Society attached themselves. The two had history: Watkins had cast Jordan in a Burn Notice guest spot between The Wire and Friday Night Lights, at one point digitizing a VHS copy of Jordan's reel so the network could approve him.
Watkins acknowledged that an authorized portrait carried risks, particularly with a figure who has "ascended to almost deity status." Lonnie Ali is an executive producer, and Watkins said trust ran in both directions. When he proposed exploring unflattering family material, including panic attacks Ali rarely discussed publicly and domestic violence in the boxer's parents' marriage, she told him: "I'm OK with all of it as long as you tell the truth." That became the show's organizing principle. The early episodes frame Ali's fraught relationship with his father, Cassius Clay Sr., as central, recasting the fighter's eventual name change as more than a statement of religious conversion.
Casting the lead took a year and a half. Watkins told casting director Kim Coleman he wanted a newcomer with an athletic background, ideally from the Southeast, and, as he put it, somebody with daddy issues. Coleman searched boxing clubs, regional and community theater and acting classes rather than normal channels. Jaalen Best, who had largely given up on Hollywood and moved back to North Carolina, sent in a tape. His first audition was a full-on Ali impersonation, which Watkins said was good but exactly what he did not want, so Best taped again as himself. The field of hundreds, perhaps thousands, narrowed to four finalists, who underwent a three-day physical evaluation at a Los Angeles gym with trainer Rob Salley. Watkins did not warn the actors they would meet one another. "I wanted to see who had that quality" of walking in with Ali-like certainty, he said.
Jordan, Watkins said, takes producing seriously and gives strong story notes, and his clout proved decisive. After Amazon's leadership changed and the already greenlit show was "really hanging by a thread," Jordan rearranged his schedule to attend key meetings in person, which Watkins said helped clinch the deal.
The production also chased scale. Watkins wrote a sequence set in the Roman Colosseum into the script without believing it was possible, and said the series became the first and only television production allowed to film there. When he asked why the venue said yes, he was told: "Because it's Muhammad Ali, and because it's our history too."
