HBO’s Winning Time is a delicate dance of intention and improv, not unlike the 1980s Lakers

Editor’s note: All interviews for this story were completed prior to the SAG-AFTRA strike.

Despite winning a championship during Magic Johnson’s rookie year, Los Angeles Lakers assistant coach Pat Riley was so stressed he wore a neck brace for six weeks during the 1981 postseason.

Riley’s tension is evident during the second season of Winning Time: The Rise of the Lakers Dynasty, which premieres Sunday on HBO. The Lakers had clashing basketball ideologies: then-head coach Paul Westhead’s rigid and deliberate offense named The System versus Riley’s fast-paced and more improvised style.

When Westhead’s system failed, the Lakers fired him after just 11 games in 1981. Riley moved in as the replacement, instituting his run-and-gun style that became known as Showtime basketball. It was a literal change of pace for the Lakers, who began playing much faster on their way to a 1982 championship.

Kareem Abdul-Jabbar reflected on these contrasting philosophies, writing last year that he felt Westhead’s “methodical, tactical approach” actively stifled Johnson’s spontaneity. He added that the best moments with Johnson “were less choreographed and more like jazz” while on the court.

The pressure points between The System and Showtime, two dramatically different approaches, are a central theme in the second season of Winning Time. Decades later, the cast and crew of Winning Time worked to find the right balance with their own craft while on the set of the show as well.

They found themselves in a fairly similar position and the actors on the show are aligned with Johnson and the 1980s Lakers: They, too, prefer creativity over rigidity. But most are seeking at least some sense of balance. Max Borenstein, the showrunner for Winning Time, said that is all intentional and deliberate.

“There is a quality to the show as the whole team executes it that feels fun, and sometimes has an improvisatory vibe,” Borenstein explained to For The Win. “Sometimes it is improvised, and sometimes it just feels that way.”

Jason Segel portrays the rules-oriented Westhead, but his origins as an actor working with director Judd Apatow on the television series Freaks and Geeks were more improvisational by nature. He predominantly found himself in those types of playful comedic roles until he was cast as the author David Foster Wallace in a 2015 drama.

“I kind of cut my teeth in improv comedy, which is the run-and-gun Showtime-era approach,” Segel said. “Then I did a movie called The End of the Tour, which was all prep. I was scared. The only way I was going to accomplish it was if I prepared really, really hard.”

Segel has come to learn that there is a perfect middle ground in these two worlds.

“It is a combination of those two things. It is intense prep so that by the time you are shooting, you have complete freedom,” he added. “You’re not thinking about your lines because you know them perfectly. If something else happens, it happens. But it’s all built on the intense prep you did before.”

Brody, who plays Riley, stressed the importance of malleability. But he noted that the filmmakers ultimately have the final say in helping these ideas come to life on the screen, deferring to the de facto “coaches” of the production.

“Sometimes too much freedom doesn’t give you enough boundaries, and you can go way off. That’s why you need a great director,” Brody said. “That’s why we rely upon directors and filmmakers to have a vision and an overall vision and to make sure that what you think you’re bringing fits within it.”

Playing the exuberant Johnson, Quincy Isaiah said it’s not unlike listening to a coach.

“You got to lean on your leaders and trust that they will lead you to the promised land,” Isaiah said.

John C. Reilly, playing longtime Lakers owner Dr. Jerry Buss, has perhaps the strongest improvisational background of any actor on the show. Many of his most famous and iconic roles, including his appearances on The Tim and Eric Awesome Show, were largely improvised.

“I personally think actors are the best when they feel like they can do anything,” Reilly said. “It doesn’t matter. When the camera rolls, do whatever you feel. Whatever seems genuine. But I think a great director will always say, ‘You give me one just as written, and I’ll give you one where you do whatever comes out of your mouth.’”

Some of his approach comes with years of first-hand experience working alongside Winning Time executive producer Adam McKay, including in leading roles for Talladega Nights (2006) and Step Brothers (2008).

Reilly said that especially in the moment while filming, it is impossible to tell which take was actually the best one for the project.

“They’re going to pick one moment that’s best and those editors don’t give a [expletive] whether it came from the script or whether you made it up in the moment,” Reilly explained. “They just want the best moment.”

Michael Chiklis — who plays Celtics executive Red Auerbach and previously appeared in the McKay film Don’t Look Up (2021) — explained that as much as he loves to improvise with his colleagues, it is important to have structure to balance it out.

“That’s the Adam McKay school,” Chiklis said. “It says honor the script, let’s get it written as solid, and then let’s do a few where you guys can bring some improv and some jazz to it.”

Sean Patrick Small took advantage of that playbook when he was on the set of Winning Time. Sometimes, Small, portraying Larry Bird, would even ask specifically if he could do a take aimed to fail.

“Maybe you’ll get a reaction out of the other actor or maybe you’ll get somewhere by the end that you would have never thought to go and that could end up in the cut,” Small said.

That sort of approach lends itself to a fun and creative atmosphere when filming as well, according to Solomon Hughes, who plays Kareem Abdul-Jabbar.

“Especially working with this incredible cast of actors, there’s always going to be something new. Nobody is robotic,” Hughes said. “Everybody is bringing something special and unique to every take.”

This sort of environment allowed actress Hadley Robinson, who plays Lakers owner Jeanie Buss, to get out of her comfort zone.

“I came from structure, and so The System is probably something I would feel more comfortable with,” Robinson said. “I bet I would thrive in The System. But I feel like this show has allowed me to sort of do the Riley way a little bit more.”

When looking at what didn’t work about The System and what did work about Showtime, it isn’t too different when creating a show like Winning Time. Both the show and the offense require structure and extraordinary attention to detail, but it all comes to life on the screen with some unexpected and unscripted moments as well.

“The balance of Showtime between something that has a structure at its core and the ability to improvise and have fun around that feels like a really nice metaphor for what we try to achieve in the show,” Borenstein concluded.