The star-studded cast is led by John C. Reilly as Lakers owner Jerry Buss, Jason Clarke as Lakers general manager Jerry West, Sally Field as Jessie Buss, Hadley Robinson as Jeanie Buss, Adrien Brody as Lakers coach Pat Riley, Jason Segal as Lakers coach Paul Westhead, and Quincy Isaiah as Magic Johnson.
Rounding out the cast are Dr. Solomon Hughes as Kareem Abdul-Jabbar, DeVaughn Nixon as Norm Nixon, Gabby Hoffman as Claire Rothman, Tamera Tomakili as Earlitha “Cookie” Kelly, and Rob Morgan as Ervin Johnson Sr.
Based on Jeff Pearlman’s book Showtime: Magic, Kareem, Riley, and the Los Angeles Lakers Dynasty of the 1980s, Winning Time is described as a “fast-break series chronicling the professional and personal lives of the 1980s Los Angeles Lakers, one of sports’ most revered and dominant dynasties — a team that defined an era, both on and off the court.”
According to Matthew Belloni of Puck, the Buss family, the Lakers leadership, its 80s-era players, and the NBA in general all absolutely hate this show.” Aside from having no financial interest in the show, Belloni says these parties “feel HBO and McKay have taken real people and turned them into a fictionalized ’80s version of Entourage or Ballers. According to someone who’s seen the pilot, it’s raunchy, filled with drugs and womanizing, and it is said to portray Buss as a misogynist party boy.”
Winning Time is also the show that led to the creative split between McKay and longtime collaborator Will Ferrell. As McKay recently revealed, Ferrell had wanted to play the role of Jerry Buss and became incensed after learning that McKay had replaced him with their longtime friend, Reilly.