‘The Greatest’ Boss Unpacks Epic Finale Battle, Reveals 3-Season Hopes for Muhammad Ali Series

Ben Watkins and stars Jaalen Best and Amin Joseph tell TheWrap about the casting process and filming that Sonny Liston brawl

The-Greatest
Jaalen Best in "The Greatest" (Prime Video)
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Note: The following story contains spoilers from “The Greatest.”

Just as its title indicates, “The Greatest” takes on the task of portraying the life of acclaimed boxer and activist Muhammad Ali in the first authorized scripted series about his life. But it was exactly that legacy that led showrunner Ben Watkins to take Ali’s life piece by piece, starting with a coming-of-age story.

“Everybody who hears the name Muhammad Ali pictures a fully-formed legend — maybe we should introduce them to a person,” Watkins told TheWrap. “Yes, we’re going to have the key big moments in his life, but let’s not have that be the purpose of the show. Let’s show the small, intimate brick building of the foundation of the man that would one day become Muhammad Ali.”

To achieve that level of detail, Watkins pulled out the defining moments of Muhammad Ali’s rise, introducing an 18-year-old Cassius Clay who had just won a gold medal at the 1960 Rome Olympics, and was determined to become heavyweight champion as soon as he could — a title he would earn at age 22 just four years later. Those years also mark Ali’s embrace of the Nation of Islam —which led to controversy both in media and boxing circles as well as within his own family — leading up to him taking on the name Muhammad Ali after earning the title.

“You win the gold medal in ’60, you win the heavyweight title in ’64, and along the way, you go from being a kid to becoming a man,” Watkins said. “You go from being Cassius Clay to becoming Muhammad Ali.”

Achieving his goal of becoming heavyweight championship bookends the first season of “The Greatest,” as Ali (Jaalen Best) takes on rival Sonny Liston (Amin Joseph), whose journey is also shown side-by-side Ali’s during the eight episodes.

But their fight was anything but easy, with Ali temporarily blinded after a particularly brutal hit from Liston. The intensity of the fight was felt by the actors, with the three-day shoot in the ring marking the culmination of over a year of training for Best and just under that for Joseph.

“This is the finale, this is the crescendo, this is … the climactic thing here, and it’s like man, all of the preparation, all of the calorie restrictions, all of the two-a-days … and now finally we’re in a ring together over three days, and all the lights and all the cameras on this choreography that now we know like the back of our hand — that is so surreal,” Joseph told TheWrap. “You just pinch yourself and go, ‘Man, I think we’re creating something.’”

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Giovanni Ribisi and Jaalen Best in “The Greatest” (Prime Video)

While the finale ends the battle for heavyweight champion, Watkins has hopes to portray more of Muhammad Ali’s life with two more seasons, which don’t officially have a green light from Prime Video. But Watkins notes Season 2 is “being discussed right now, and there’s a lot of enthusiasm around around it,” adding that reception for Season 1 will be a “deciding factor.”

“From the beginning, I always pitched it as three seasons,” Watkins said. “I wanted to pick very key moments that I felt were representative of the mythology of Muhammad Ali, and I wanted to pick three seasons, but always with the intent that we will go behind the scenes, we will turn the the lights off and stop the cameras rolling and show you all the connective tissue in between the big moments.”

Watkins revealed that with Season 1 portraying 1960-64, Season 2 will focus on ’67-’71, following another “key portion” of Ali’s life that saw him banned from boxing after refusing to be inducted into the armed forces during the Vietnam war, citing his religious beliefs, before coming back in the “Fight of the Century” with Joe Frazier.

The final season would take place from ’74-’77, but Watkins intends to flash forward to 1996 when he lit the cauldron in the Olympics, and revealed flashbacks could be used in Season 2 to fill in the gaps following the assassination of Malcolm X in 1965.

TheWrap: How this project first came together? 

Watkins: There was a producer who, by the name of Josh Wakely, who really is a been a lifelong Ali fan, just like me. He started the wheels rolling early on, saying he wanted to do something Ali related, and he got Universal Music Group interested. Then he got Authentic Brands interested. That got him to Lonnie Ali. He went to Louisville to do research, got close to the family, and then he got Roc Nation and Jay Z interested in this. This critical mass started building, but they weren’t getting traction in a way where they could get the show set up.

And then Michael B. Jordan got interested in with his company Outlier, and they were at Amazon, and I was doing a show for Amazon, and that’s when it got to me. I had heard of the project, but was really hesitant to engage because that’s my lifelong hero. I’m not going to tell that story and mess it up. But then I realized with the advice that I give to everyone that is a writer and really to all artists is you should do the thing that scares you. I feel like if it scares you, is probably really close to a truth for you, and I wasn’t listening to my own advice, so I decided to go ahead and lean into the story. To have Lonnie Ali as an EP on this show, somebody who has protected this legacy and uplifted the legacy, but also could connect me with all these people that go beyond the books and the videos and the documentaries and the movies, but actual real people that were connected to Ali gave me an insight and an advantage that I felt was game changing.

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Dana Gourrier, Jaalen Best and Kai Parham in “The Greatest” (Prime Video)

How did you find your Muhammad Ali? How many actors did you look at and what made you confident Jaalen was the right pick?

We started that search as soon as I finished the first script. We didn’t know if we were going to get greenlit, but we knew there was enthusiasm. And I said, “we have to start the search now because it’s going to be tough. And if we don’t find the right Muhammad Ali, maybe we don’t do justice to this story.”

We got Kim Coleman involved, who I’ve been working with for years, one of the best casting directors ever, and in this case, she had to find a newcomer. I didn’t want anybody tuning in and saying I recognize that actor from somewhere, so she couldn’t go to all the unusual spots. She was going to boxing gyms, off Broadway, regional theater groups. She was searching everywhere, all the nooks and crannies, and somehow she starts pulling in these options. And Jaalen Best was one of them. And his early audition, I saw resemblance to Muhammad Ali, but I also saw someone who was doing an impersonation of Muhammad Ali, so I actually made him re-tape and just said, “I need you to do it as the character, not as Muhammad Ali.” And he did that, and that was the beginning of what turned into a two-year process. It was 18 months of the search, narrowed it down to four people, multiple rounds of auditions, multiple meetings.

They all had to go to do a physical eval … but that first day, I made them show up together because in my mind everything was a test, and one of the tests was if you could play Muhammad Ali, you’re okay with the threat of competition because you think you’re destined to do this. And when I hear Jaalen talk now, he said that’s how he approached the whole process. He had to approach it like the role was his, not like it was a role he might get. And he always, no matter how good the competition was, he always wound up at the top of the heap at every level. So by the end of that process, it was a no-brainer. The last step was sending him to meet Lonnie Ali … 10 minutes after he gets to Louisville, I get a message from her, and she said, “Ben, he is the one in more ways than you know.”

It’s a massive responsibility to play such an iconic figure as Muhammad Ali. what was the audition process like and what was it like taking on the role?

The audition process was very lengthy. It was about a year-long process … it was maybe 2023 whenever I got the first audition … it’s almost four years. It’s an honor to be able to see life through his lens and to be able to do that at such a young age for me, where I still have my life to live, and it makes me be able to ask the question, “what do I want to stand for?” and so I think that was my mentality throughout this entire process, getting to learn about you know a person that the world calls their hero, and get to discover why he’s my hero.

This interview has been edited for length and clarity.

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