John C. Reilly as Jerry Buss
With the help of a combover, mustache and print-filled wardrobe, the Walk Hard: The Dewey Cox Story star transforms into the self-made millionaire and majority owner of the Lakers during the team's Showtime era.
Prior to Reilly joining the series, Michael Shannon was set to portray the larger-than-life Dr. Buss, but he dropped out due to creative differences. "It really bugged Michael that we were breaking the fourth wall," executive producer Adam McKay explained to The Hollywood Reporter. "He kept saying, ‘I don't like this. It throws me. I'm having a hard time.'"
The casting decision would end up causing the ongoing rift between McKay and longtime friend and collaborator Will Ferrell, who expressed his interest in playing Buss and only learned Reilly would be taking over the part after he received a call from his Stepbrothers co-star.
Looking back, McKay admitted to THR that he "f--ked up" by not reaching out to Ferrell beforehand.
"It was at this weird moment where Will and I weren't exactly hugging each other, even though there was nothing that terrible and he called Will and said, 'Hey, McKay just came to me with this,'" McKay recalled. "And Will was very hurt that I wasn't the one to call him, and I should have."
Reilly, meanwhile, said, "Will is one of my best friends, Adam is one of my best friends, I was delighted to get the job and that's all I really have to say."
Quincy Isaiah as Magic Johnson
Talk about a magical debut role. The newcomer portrays one of basketball's most iconic stars in his rookie season with the Lakers after he is the No. 1 overall pick in the 1979 NBA draft.
The pressure was on for the Winning Time producers to find the perfect actor, with the series coming close to falling apart during what McKay called the "craziest casting experience" of his career.
"I turned to [producer] Kevin Messick at one point and said, 'We can't do this with a subpar Magic Johnson,'" McKay revealed to THR. "I mean, it's him, Dr. Buss, Jeanie and Kareem, that's the story. But the smile at the middle of it, what brought it all together, was Magic Johnson. So if we can't get this guy, we can't make the show.'"
They found him in Isaiah, who, like Johnson, was a Michigan native. But first, the former college football player had to undergo a basketball audition with former Lakers star Rick Fox.
"I wanted to see how bad he wanted it," Fox said. "He'd lean over and grab his shorts, and then he'd see me looking, and he'd stand up quickly and pop that smile like only Magic would."
Hadley Robinson as Jeanie Buss
Playing Jerry's ambitious daughter—who eventually goes on to become the controlling owner and president of the organization, NBD!—is played by the Moxie actress.
Jason Clarke as Jerry West
Meet "the Logo"!
The Australian actor is playing the Lakers all-star point guard for the championship-winning team who later spent head coach for three seasons. He left that position to become a scout and, eventually, general manager in 1982. And yes, the player silhouette in the NBA's trademark logo is West.
Gaby Hoffmann as Claire Rothman
The Now and Then star plays the L.A. Forum general manager and Buss confidant, who is credited with turning the front row at Lakers' games into a celebrity hot spot.
Solomon Hughes as Kareem Abdul-Jabbar
It's a tall order to play one of the sport's most notable stars. And standing at 6'11", Hughes, who played basketball at the University of California, Berkeley comes close to the 7-foot-2 six-time MVP.
"Kareem's one of the most complex and interesting people in American history," McKay told THR of finding the right actor. "He's the all-time leading scorer in the NBA, he's a voice for a people and a movement, a writer, a thinker and a jazz aficionado."
Before being cast as Jabbar in his acting debut, Hughes was a member of the Harlem Globetrotters and working in academia, and he was just finishing up a stint a Stanford University when he heard about the project. H lost 25 pounds for the role and attempted to connect with Jabbar, who declined to meet with Hughes. In fact, most of the IRL players were not particularly pleased with the project, including Johnson, who told TMZ, "I'm not looking forward to it. I'm going to leave it at that."
Adrien Brody as Pat Riley
The Oscar winner undergoes his most dramatic transformation yet to play one of the league's best coaches of all-time. After his playing days ended in 1976, Riley wasn't sure of his future with the organization, but ultimately led the Lakers to four NBA championships and unprecedented superstardom, becoming known along the way for his slick courtside style.
To land the gig, one of Brody's reps sent an email to the producers with side-by-side shots of the actor and Riley to show just how similar they look.
DeVaughn Nixon as Norm Nixon
No, the shared last name isn't a mere coincidence as DeVaughn is the son of the two-time NBA champion, who initially clashed with Johnson for the position of point guard.
Jason Segel as Paul Westhead
Taking on the role of the assistant coach, who would go on to lead the team by the end of the 1980 season, is the How I Met Your Mother alum.
Sean Patrick Small as Larry Bird
The actor and writer grew up a major fan of the Boston Celtics legend, who was Johnson's rival dating back to their college days. In fact, Small even wrote a four-part miniseries based on When March Went Mad: The Game That Transformed Basketball, a book that documented their epic rivalry.
And Small told Deadline he is hoping Winning Time could help his passion project get picked up by a network, saying, "We're still pitching, we're trying to get it off the ground."
Before Small was cast as his childhood idol, Bo Burnham was set to portray Bird, but had to drop out of the series due to scheduling conflicts.