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It’s Time to Relive All the Winning Time Drama

Photo: Warrick Page/HBO

Winning Time, for better or for worse, has A LOT of people talking. Whether it’s arguing about how its Lakers stars are portrayed or an in-depth discussion on why the show needs to look like that, the series is on people’s minds and in their group-chat discussions. But all press is good press, as the show has been renewed for a second season. But you’re not here for happy endings. You’re here because you love drama! Suspense! Action! Surprised? Oh, did you think we would be able to break down all the Winning Time drama without using voice-overs? Think again. If only we could access a sepia filter.

It’s Showtime! Oh, wait.

A series based on a book titled Showtime, after the era of Lakers history commonly known as “Showtime,” would be called Showtime, right? Not if it’s streaming on HBO. Named after the Horn nightclub’s signature phrase to kick off a night of partying, the Lakers’ Showtime era stemmed from Jerry Buss’s desire to make basketball games feel like the hottest ticket in town. However, once the show (based on the book Showtime: Magic, Kareem, Riley, and the Los Angeles Lakers Dynasty of the 1980s) received a pilot order from HBO in April 2019, it needed a name that definitely wasn’t Showtime to avoid “marketplace confusion” with HBO’s rival network, Showtime. The pilot was picked up to series in December 2019 and received a new name: the Untitled Lakers Project. It finally landed the Winning Time title almost two years later, when HBO released first-look photos in December 2021. HBO executive Casey Bloys confirmed to The Hollywood Reporter that “if there were not a pay cable or streaming platform called Showtime, maybe it was a different conversation. But I will say that ‘winning time’ is a Magic Johnson phrase.” Let’s just say the word Showtime for old times’ sake. Showtime!

Shows Before Bros

Will Ferrell and Adam McKay, who co-founded Funny or Die and Gary Sanchez Productions together, were at the end of the business partnership and, unknowingly, their friendship during the early stages of Winning Time. McKay, who left Funny or Die in 2018, began working on more serious, we’ll call them, film projects, starting with his 2018 film, Vice (it earned eight Oscar nominations), while Ferrell continued with comedies like Holmes & Watson with their mutual friend John C. Reilly. More on him later. Their differing career paths led to their creative breakup in their last business venture, Gary Sanchez Productions, in April 2019. Just a few weeks later, the series formerly known as Showtime got a pilot order from HBO.

McKay had to choose who would play the Showtime man himself: millionaire playboy and Lakers owner Jerry Buss. Coincidentally, Ferrell is a huge Lakers fan. Like HUGE. Enough that he started doing bits during Lakers games. Bits! A comedian’s most prized possession. He obviously would be down to play Buss. But McKay had other plans. In an interview with Vanity Fair, McKay revealed that Ferrell wasn’t an option. “The truth is, the way the show was always going to be done, it’s hyperrealistic,” he told the publication. “And Ferrell just doesn’t look like Jerry Buss, and he’s not that vibe of a Jerry Buss. And there were some people involved who were like, ‘We love Ferrell, he’s a genius, but we can’t see him doing it.’ It was a bit of a hard discussion.” Ouch. We call that unsportsmanlike conduct. McKay decided to cast Michael Shannon as the iconic owner, with Ferrell allegedly giving his blessing. But that was short-lived, as it was reported that Shannon wasn’t a fan of the show’s curious stylistic endeavors and eventually dropped out. Some would think this is a great opportunity to cast your longtime creative partner, who is obviously a fan of your creative vision, right?

But this is a post about drama — twists, turns, and unexpected endings. McKay decided to twist the knife into Ferrell’s back and cast one of their close friends: Reilly. AND he didn’t tell him beforehand. Oh, you felt that too? Reilly called Ferrell before he made his decision to accept the role. Ferrell was obviously hurt by McKay not letting him know, which resulted in the end of their friendship in September 2019. McKay still regrets how he handled the whole situation. “Will was very hurt that I wasn’t the one to call him, and I should have. I fucked up,” McKay said to THR. There have been no updates as to whether or not Ferrell and McKay have made up. Aw! But everyone seems happy with how the casting turned out, right? Right?!

How the Real Jerry West Was One Angry Fella

Now that we have our fictional Buss, we’re good, right? No more drama? Welcome the real Jerry West to the chat. West, who is portrayed as a sad, angry man in Winning Time, is very upset with HBO — so much so that he wants to bring the Supreme Court into it. He sent a letter to HBO from his legal team demanding a “retraction and an apology” from the network for portraying him as an “out-of-control, intoxicated rage-aholic.” He rallied other Showtime stars (former Lakers players Kareem Abdul-Jabbar, Michael Cooper, and Jamaal Wilkes, as well as office staff Claire Rothman, Charlene Kenney, Bob Steiner, and Mitch Kupchak) to write statements defending his character on his behalf.

HBO responded to West’s letter and is standing by the series, which is not touted as a docuseries. The network claims that the show is based on “extensive factual research and reliable sourcing” despite being a fictionalized depiction of the Showtime era. A very “he said, network said” situation. But it did not stop there. West fired back, claiming that he will take HBO to the most important court in the country. No, he’s not challenging the streamer to a game of H-O-R-S-E; he’s willing to take HBO to the Supreme Court. He claims that the show makes the Lakers “all look like cartoon characters.” And he doesn’t mean it in a good way, like in the original Space Jam!

Everyone’s a Critic

While some former Lakers have brought the law into the equation, others have gone the old-fashioned route: complaining about the show on the internet. Abdul-Jabbar, Lakers center and THR guest columnist, wrote about Winning Time in his Substack, a.k.a. his personal blog. While Abdul-Jabbar had a less emotional reaction to the series, he did share why he was not a fan of the show, unrelated to how he was portrayed. Normally, I’d be like, SURE, JAN! But Abdul-Jabbar is a fan of The Great, so he has good TV taste. Let’s hear him out.

When summarizing the characters of the show, Abdul-Jabbar had this to say: “Jerry Buss is Egomaniac Entrepreneur, Jerry West is Crazed Coach, Magic Johnson is Sexual Simpleton, I’m Pompous Prick.” Okay, alliteration. He also comes to the defense of Jeanie Buss and Rothman; both have not approved of the series. Abdul-Jabbar states that the show discredits Jeanie and Rothman’s accomplishments by making them into caricatures. “[Jeanie] wasn’t the naïve daddy’s girl,” he wrote. “Having Claire Rothman unbuttoning blouse buttons and flouncing her hair before meeting Jerry Buss (which she denies ever happened) reduces her intelligence and competence for a cheap joke — which is probably the kind of misogyny the women had to endure in business and now have to endure from the filmmakers.” Damn. So if he’s not a fan of the characters, does he at least think the show is funny?

“Humor is one of Adam McKay’s specialties, but he can’t seem to find any in this show,” wrote Abdul-Jabbar. Well, that answers it. He praises McKay’s other work (The Big Short) for its use of breaking the fourth wall effectively, but he doesn’t see the same spark in Winning Time. “In Winning Time, [breaking the fourth wall] is neither funny nor insightful, mostly just giving us information,” he explained. “Those bro-dude attempts are as cringy as a bad SNL skit.” And he’s coming for SNL now? Does he want to be a Vulture recapper? Now that we’ve heard from everyone, from the creators to the real-life Lakers, all that’s left is the man who unknowingly started this whole thing. 

The Pearlman Who Knew Too Much

And now we meet the man who started it all. He’s also, you guessed it, not happy with the show. But not in the same way everyone else is. Jeff Pearlman, author of Showtime: Magic, Kareem, Riley, and the Los Angeles Lakers Dynasty of the 1980s, was not spared from the drama off the court. Pearlman was first approached by co-creator Jim Hecht, Ice Age 2 screenwriter, who met him on Easter Sunday. “[Hecht] came off as very sincere. I ended up giving him the option rights to the book for free,” said Pearlman in an interview with Variety. “You really should never do that. I didn’t know what I was doing. But I never expected anything.” Pearlman didn’t believe the series would come to life, as he’s had his books optioned numerous times without success; Hecht would call him to give him updates on the development process. Even after meeting with McKay about the series, Pearlman considered it “bullshit.” It wasn’t until a friend emailed him about Reilly’s casting that it became real to him.

While Pearlman wasn’t directly involved with writing Winning Time, he did offer notes and feedback on scripts. His heavy involvement with the series didn’t come without consequences. As the Lakers stars depicted in the show began expressing their discontentment with Winning Time, Pearlman stood by the series, even if it meant losing the support of the team to which he dedicated his book. “Nobody from the Lakers will have anything to do with me,” he told The Hollywood Reporter this past February, “and it’s a bit of a bummer.” You can’t please everyone, but you can’t go back once you get drafted to another team. At least there’s another season for a redemption arc.

It’s Time to Relive All the Winning Time Drama