Full Cast of Winning Time Season 2 - Every Actor & Character In New Episodes

By Richard Nebens Posted:
Winning Time, Quincy Isaiah as Magic Johnson, John C. Reilly as Jerry Buss

Season 2 of Max's sports drama Winning Time: The Rise of the Lakers Dynasty is officially underway, with a massive cast of actors embodying the real-life characters driving its story.

Just like Season 1, Winning Time Season 2 takes a unique look into the legacy of the Los Angeles Lakers of the 1980s, who created one of the most memorable dynasties in sports history under the nickname "Showtime."

Taking a fictionalized look at that dynasty's development in the Lakers' front office and on the Great Western Forum court, Season 2 covers a full four-year span of the Showtime era rather than the single year (1979-80) highlighted in Season 1.

And while the series has stirred up controversy amongst those who lived through this era, with Lakers star Magic Johnson telling Variety that there's "no way to duplicate Showtime," the series hit the ground running for fans reminiscing on those golden years.

Winning Time Season 2 Cast & Characters

Season 2 of Max's Winning Time features 34 actors bringing the personalities from inside and around the Los Angeles Lakers' Showtime dynasty to life, many returning from Season 1 along with a few newcomers.

1.) John C. Reilly - Dr. Jerry Buss

John C. Reilly, Dr. Jerry Buss
John C. Reilly

Leading the efforts of both Winning Time and the Lakers organization is team owner Dr. Jerry Buss, a former real estate mogul in the Los Angeles area, played in this series by Oscar and Golden Globe-nominee John C. Reilly.

In Season 2, Dr. Buss has high ambitions starting off his second year owning the Lakers, looking to repeat the same success the team had in 1980 after the purple and gold won their seventh NBA championship and the second in Los Angeles.

Reilly is best known for his award-nominated efforts in 2002's Chicago and 2009's Walk Hard: The Dewey Cox Story, and he is also part of the expansive MCU with a role as Corpsman Dey in 2014's Guardians of the Galaxy.

2.) Quincy Isaiah - Earvin "Magic" Johnson

Quincy Isaiah, Earvin
Quincy Isaiah

Taking the challenge of playing an NBA legend, Quincy Isaiah portrays Earvin "Magic" Johnson, who joined the Lakers as a rookie in 1979 before helping the team win the NBA title in 1980 - he even won the NBA Finals MVP award.

Season 2 puts Magic in uncharted territory as a budding NBA veteran with some caché. Starting the season off with a gruesome injury, he looked to build a healthy relationship with his older and more experienced teammates. This all comes on the heels of signing one of the biggest contracts in NBA history.

Winning Time is the biggest credit on Isaiah's resume to date as he looks to build upon his work as Magic Johnson and move into other prominent roles.

3.) Jason Clarke - Jerry West

Jason Clarke, Jerry West
Jason Clarke

Coming back from Season 1 is Jason Clarke as he embodies Jerry West, a 14-time All-Star and former NBA champion with the Lakers who serves as the team's general manager after a failed stint as head coach.

Season 2 sees West put to the test over the early 1980s as players and coaches clash with one another, all while he makes some potentially risky personnel moves in order to keep the Lakers on top of the professional basketball world.

Along with his roles in 2012's Zero Dark Thirty and 2015's Terminator Genisys, Clarke was most recently part of the massive cast featured in Christopher Nolan's 2023 historical epic Oppenheimer.

4.) Adrien Brody - Pat Riley

Adrien Brody, Pat Riley
Adrien Brody

Oscar-winner Adrien Brody returns for Season 2 as Lakers coach Pat Riley, who goes into Season 2 to take over as the team's head coach before winning the first of his four NBA championships in the City of Angels.

Quickly moving his way up the Lakers staff from being one of the team's broadcasters to taking on a coaching position, Riley finds himself diving right into the fire as he leads the way for some of the team's toughest on-court battles.

Brody is best known for his Oscar-winning role as Wladyslaw Szpilman in 2002's The Pianist, and he starred more recently in Apple TV+'s Ghosted and 2023's Asteroid City.

5.) Gaby Hoffmann - Claire Rothman

Gaby Hoffmann, Claire Rothman
Gaby Hoffmann

Gaby Hoffmann embodies one of the Lakers' unsung heroes in Winning Time, Claire Rothman, who serves as the President and General Manager of the Great Western Forum in Los Angeles, California, the Lakers' home arena.

Rothman is the first and only female manager of any sports arena in any major city, using her high intelligence and fortitude to become a success story in a male-dominated industry.

Hoffman is in the midst of an incredible 34-year career in the film industry, boasting roles in projects like Uncle Buck (1989) and Field of Dreams (1989) amongst her nearly 50 credits.

6.) Tracy Letts - Jack McKinney

Tracy Letts, Jack McKinney
Tracy Letts

Season 1 of Winning Time saw the Lakers promote Tracy Letts' Jack McKinney to the position of head coach, although he only lasted 14 games with the team before an injury forced him to vacate the job.

Even being the mastermind behind the Lakers' uptempo-style playing style that earned them the "Showtime" nickname, his lack of experience in the pros didn't help in his endeavor to be successful before moving on to other coaching jobs.

Letts was part of a number of impressive projects over the last few years including 2017's Lady Bird and 2019's Little Women, and he also played Henry Ford II in 2019's Ford v Ferrari.

7.) Jason Segel - Paul Westhead

Jason Segel, Paul Westhead
Jason Segel

Jason Segel takes on the intriguing role of Paul Westhead, who takes over as the Lakers' head coach after McKinney suffers a major bike-riding injury early into the 1979-80 season.

Coach Westhead goes on to win the 1980 championship alongside Magic Johnson, although Season 2 sees him butting heads with players and management before he's let go in favor of Pat Riley.

Along with his legendary role as Marshall in How I Met Your Mother, Segel's more recent credits include a role alongside Harrison Ford in Apple TV+'s Shrinking along with comedic roles in This is 40 and The Muppets.

8.) Julianne Nicholson - Cranny McKinney

Julianne Nicholson, Cranny McKinney
Julianne Nicholson

Emmy-winner Julianne Nicholson plays the key supporting role of Cranny McKinney, the wife of Jack McKinney, who is seen supporting her husband through his injuries and his rocky tenure as the Lakers' coach.

Nicholson's Emmy win came after her performance as Lori Ross in Mare of Easttown, and she also has experience in high-profile biopics like I, Tonya, and Black Mass.

9.) Hadley Robinson - Jeanie Buss

Hadley Robinson, Jeanie Buss
Hadley Robinson

Played by Hadley Robinson, the young and ambitious Jeanie Buss comes into play in Winning Time as she works her way up the ranks of Lakers management under the guidance of her father, team owner Dr. Jerry Buss.

While she experiences plenty of pushback early on for her ideas, Jeanie eventually finds her way on the business side working with the Lakers and the Great Western Forum, and she even takes over as team owner in real life after her father's death.

Although she has less than a dozen credits on her resume, Robinson is recognizable from her role as Sallie Gardiner Moffat in 2019's Little Women.

The real world's Jeanie Buss has also shown support for Winning Time, telling Los Angeles' AM 570 LA Sports radio show in August 2023 how much she misses her late father and how "it's kind of nice to see him" through this scripted series.

10.) Dr. Solomon Hughes - Kareem Abdul-Jabbar

Dr. Solomon Hughes, Kareem Abdul-Jabbar
Dr. Solomon Hughes

Winning Time gives a great deal of shine to the Lakers' starting center from the 1980s, six-time NBA MVP Kareem Abdul-Jabbar, with 6-foot-11-inch Dr. Solomon Hughes giving an inspired performance as the real-world 7-foot-2-inch superstar.

After being sidelined for Game 6 of the 1980 NBA Finals with a severe ankle injury and watching Magic win the Finals MVP award, Abdul-Jabbar returned in Season 2 with his unique and aloof personality as he worked his way back into the fold.

Following a brief stint as a semi-professional basketball player with the Harlem Globetrotters and a tenure as a professor at Stanford University, Winning Time became Dr. Hughes' very first acting credit in 2022.

Tamera Tomakili, Earlitha “Cookie” Kelly
Tamera Tomakili

Magic Johnson's longtime wife, Earlitha “Cookie” Kelly, is played by Tamera Tomakili as the on-again, off-again couple pushes through their early years together while Magic begins his career in the NBA.

Due to Magic's newfound worldwide fame and his travels across the country, Cookie and Magic go through plenty of trials and hardships with one another as Cookie's patience and fortitude are tested thanks to her love for her sweetheart.

With just over half a dozen credits on her resume, Tomakili is best known for her role alongside Michael B. Jordan in Ryan Coogler's Fruitvale Station and a three-episode run in FX's Blindspotting.

12.) Brett Cullen - Bill Sharman

Brett Cullen, Bill Sharman
Brett Cullen

Becoming one of the NBA's most influential pioneers as a four-time champion, a coach, and the Lakers' eventual general manager, Bill Sharman takes the spotlight in Winning Time behind a performance from Brett Cullen.

This series highlights Sharman nearly two decades after his playing days are over as he starts to lose his voice, being forced to consider his future as the Lakers look to remain successful.

Lasting in Hollywood for over 40 years, Cullen's biggest roles actually come from the comic-book movie realm, playing a congressman in The Dark Knight Rises and  Johnny Blaze's father, Barton Blaze, in 2007's Ghost Rider next to Nicolas Cage.

13.) Stephen Adly Guirgis - Frank Mariani

Stephen Adly Guirgis, Frank Mariani
Stephen Adly Guirgis

Stephen Adly Guirgis plays a minor supporting role in Winning Time Season 2 as real estate entrepreneur Frank Mariani, Jerry Buss' best friend and business partner, who goes all-in with Buss as the pair look to win big in the NBA.

Guirgis has been in the industry for over 25 years, with credits in movies like 2018's Vice and 2014's Birdman (The Unexpected Virtue of Ignorance).

14.) Joey Brooks - Lon Rosen

Joey Brooks, Lon Rosen
Joey Brooks

Magic Johnson's eventual agent and business partner, Lon Rosen (played by Joey Brooks), is shown working his way through the industry alongside Jeanie Buss as one of the youngest employees of the Great Western Forum.

Brooks' resume is only eight credits deep up to this point in time, with his biggest project being a one-episode stint on the highly successful HBO show Succession in 2018.

15.) Sarah Ramos - Cheryl Pistono

Sarah Ramos, Cheryl Pistono
Sarah Ramos

Kareem Abdul-Jabbar's romantic life is highlighted in Winning Time via Sarah Ramos' Cheryl Pistono, who serves as the Lakers center's girlfriend in the show's first two seasons.

Pistono is a much different person than the usually reclusive and quiet Abdul-Jabbar, using her warmth and outgoing personality to bring the NBA superstar out of his shell during his long stint with the Lakers.

Recently starring in an episode on FX's The Bear, Ramos also played a central role as Haddie Braverman on NBC's Parenthood.

16.) Spencer Garrett - Chick Hearn

Spencer Garrett, Chick Hearn
Spencer Garrett

Spencer Garrett embraces the challenge of playing a central figure in Lakers history, Chick Hearn, who became arguably the most famous TV announcer in sports history.

Winning Time Season 2 shows Hearn in the middle of his 37-year career as the Lakers' main broadcaster, calling games with his unique voice as he added a new flair for fans watching the Showtime era unfold.

Boasting over 220 credits, including a small role as a town sheriff in the MCU's Iron Man 3, Garrett is best known for movies like Air Force One, Bombshell, and Once Upon a Time in Hollywood.

17.) Molly Gordon - Linda Zafrani

Molly Gordon, Linda Zafrani
Molly Gordon

Molly Gordon's Linda Zafrani is seen working in the Forum Office as the Buss family takes over Lakers ownership, having to navigate plenty of different relationships through the organization over the years.

Taking on a supporting role in Season 2 of The Bear, Gordon enjoyed an impressive run throughout 2023 with credits in projects like Theater Camp and You People.

18.) DeVaughn Nixon - Norm Nixon

DeVaughn Nixon, Norm Nixon
DeVaughn Nixon

DeVaughn Nixon brings a family theme to Winning Time as he actually portrays his own real-life father, Norm Nixon, who joined the Lakers' starting lineup as the point guard starting in 1977 until Magic came to town.

This series sees Nixon living a playboy lifestyle and even becoming an NBA All-Star in 1982, although his ego oftentimes gets the better of him battling with Magic for playing time and the spotlight, even while winning a couple of championships.

DeVaughn Nixon joined Hollywood at a young age with roles in films like Terminator 2: Judgement Day and The Bodyguard, and he also had a nine-episode run in Marvel's Runaways on Hulu.

19.) Delante Desouza- Michael Cooper

Delante Desouza, Michael Cooper
Delante Desouza

Industry newcomer Delante Dezouza joins the Lakers' fictionalized roster as defensive ace Michael Cooper, who would go on to win five championships with the Lakers while being named to the NBA's All-Defensive team in eight seasons.

Winning Time shows Cooper in his early days after a horrible knee injury forced him to miss his rookie season, learning the ropes of the NBA and Los Angeles alongside Magic and the rest of his teammates.

Outside of a couple of short movies, Winning Time is the only true credit on Desouza's resume as he adds his own flair to this take on Lakers history.

20.) Jimel Atkins - Jamaal Wilkes

Jimel Atkins, Jamaal Wilkes
Jimel Atkins

Veteran All-Star Jamaal Wilkes is played by Jimel Atkins, with the Lakers star being more of a soft-spoken and good-natured player who's often overshadowed by the bigger personalities and egos on the Lakers.

Thankfully, Wilkes is able to handle all of the distractions and the lights with poise while making a name for himself as one of the NBA's best players, even earning the nickname "Silk" as he won two of his three championships in Los Angeles.

Atkins only has a few other credits on his resume outside of Winning Time, including six episodes on David Makes Man and a single episode on Mindhunter.

21.) Michael Boucher - Jack Curran

Michael Boucher, Jack Curran
Michael Boucher

Michael Boucher's Jack Curran held the job of Lakers trainer in the late '70s and early '80s, being the first in that position to work with the Showtime Lakers as they kickstarted their run of dominance in the '80s.

Boucher's resume mostly includes single-episode appearances on a number of network TV shows, including Scorpion, Justified, and Dead to Me.

22.) Austin Aaron - Mark Landsberger

Austin Aaron, Mark Landsberger
Austin Aaron

Mark Landsberger spent half of his seven-year NBA career in Los Angeles as he played back-up center to Abdul-Jabbar, and he's played in this series by Austin Aaron.

Aaron only has three credits to his name including Winning Time, although he enjoyed a three-season stint as Luke Holliday on Netflix's hit series 13 Reasons Why.

23.) Rob Morgan - Earvin Johnson Sr.

Rob Morgan, Earvin Johnson Sr.
Rob Morgan

With both seasons of Winning Time diving into Magic Johnson's life away from basketball, his family gets plenty of shine as well, with Rob Morgan portraying Earvin Johnson Sr. as the Michigan native watches his son grow into a global icon.

Working as a garbage man and on an automobile assembly to provide for his kids, this series shows the differences between Earvin Sr. and Earvin Jr. as the family learns what money and fame truly bring into their lives.

Morgan is memorable to Marvel fans for his role as Turk Barrett in multiple Netflix shows from the Defenders Saga, and he's also famous for playing Sheriff Powell across the first four seasons of Stranger Things

24.) Kirk Bovill - Donald Sterling

Kirk Bovill, Donald Sterling
Kirk Bovill

Kirk Bovill is seen playing a minor role in Winning Time as Donald Sterling, the stingy and tough owner of the crosstown San Diego/Los Angeles Clippers, who consistently struggle in the fight for citywide supremacy.

Lacking a sense of tact or empathy, Sterling is shown as quite a negative figure in town, which preceded the infamy that came with his public image decades later involving a sexist and racist rant that went public in 2014.

Along with minor roles in TV shows such as Better Call Saul and CSI: Vegas, Bovill's biggest role is actually in another project based on real-world events, playing former United States Secretary of State Henry Kissinger in 2018's Vice.

25.) Michael Chiklis - Red Auerbach

Michael Chiklis, Red Auerbach
Michael Chiklis

Red Auerbach serves as one of the Lakers organization's biggest antagonists with his job as the general manager of the team's ultimate archrival, the Boston Celtics, as he's brought to life by industry veteran Michael Chiklis.

Winning a then NBA-record nine championships as the Celtics' coach before masterminding seven other titles, Auerbach is at the height of his powers as an executive in Winning Time as he looks to get inside the Lakers' heads at every turn.

Recognized in leading roles from The Shield and Gotham, Chiklis is certainly most recognizable for his part as Fox's original live-action Fantastic Four, playing Ben Grimm/the Thing in 2005's Fantastic Four and 2007's Fantastic Four: Rise of the Silver Surfer.

26.) Carina Conti - Paula Abdul

Carina Conti, Paula Abdul
Carina Conti

Carina Conti brings a real-world Los Angeles entertainment icon to life by playing Paula Abdul, who has the start of her career highlighted in Winning Time as she helps to get the Laker Girls dance team off the ground.

Dr. Buss adds a new form of entertainment to life by starting the Lakers Girls and having them perform at home games, with Abdul becoming one of the stars of the group as the Lakers rise to power on the court.

Conti's biggest credit to date comes with a four-episode stint in Season 3 of Freeform's Good Trouble.

27.) McCabe Slye - Jimmy Buss

McCabe Slye, Jimmy Buss
McCabe Slye

McCabe Slye portrays the youngest member of the Buss family, Jimmy Buss, Jeanie's youngest brother and an eventual key piece of Lakers management as he starts his run in the 1980s.

Before eventually taking over the team from his father in the 21st century to minimal success, Jimmy Buss is shown as a young and ambitious go-getter in this show as he and his siblings learn the ropes from their father.

Slye's biggest role to date can be seen in Rise, in which he has a three-episode run as a character named Travis.

28.) LisaGay Hamilton - Christine Johnson

LisaGay Hamilton, Christine Johnson
LisaGay Hamilton

Magic Johnson's mother, Christine, helps to serve as an emotional backbone for her son, as LisaGay Hamilton teams up with Rob Morgan to give Quincy Isaiah's leading character his own set of parents.

Christine is seen as a natural leader in her community with the ability to command a room thanks to her charisma, and she does everything she can to keep Magic grounded as he learns to handle his newfound fame.

In 2023 alone, Hamilton appeared on screen in Will Trent and The Boogeyman, and she's best known for her longstanding role as Rebecca Washington in The Practice from 1997 to 2003.

29.) Ari Graynor - Honey Kaplan

Ari Graynor, Honey Kaplan
Ari Graynor

Ari Graynor is introduced in Winning Time Season 2 as Honey Kaplan, a new love interest for Dr. Jerry Buss who he was actually with before his rise to power as an NBA team owner.

There is actually no single direct person for Honey in real life from whom Winning Time takes inspiration, although she's most likely inspired by a couple of different partners of Buss that were made into a more fictional character.

Graynor is recognizable from a number of memorable movies, with roles in films like Nick and Nora's Infinite Playlist (2008) and The Disaster Artist (2013).

30.) Andy Hirsch - David Stern

Andy Hirsch, David Stern
Andy Hirsch

Andy Hirsh's David Stern is shown in Winning Time as the NBA's legal council, looking to use Magic Johnson and Larry Bird's star power and personal rivalry to revive interest in the league before it falls into ruin.

Later into Season 2, fans see his rise to the position of NBA Commissioner in 1984 - a position would then hold for an impressive 30 years before the real Stern retired from the position in 2014.

Winning Time is Hirsh's second historical sports drama this year alone after playing a small role in Ben Affleck's Air, and he also added his voice talents to The Super Mario Bros. Movie.  

31.) Gillian Jacobs - Chris Riley

Gillian Jacobs, Chris Riley
Gillian Jacobs

Gillian Jacobs' role in this series is that of Chris Riley, the wife of eventual Lakers head coach Pat Riley, although Chris has her own place in the story next to her hardworking husband.

Jacobs' supporting character works as a therapist, using her emotional expertise to help her husband through his job and even helping shape the Lakers into the team they need to be to win it all.

Currently playing an ongoing role in Amazon Prime Video's hit animated series Invincible as Atom Eve, Jacobs also played Britta Perry on the six-season hit series Community.

32.) Newton Mayenge - Jim Chones

Newton Mayenge, Jim Chones
Newton Mayenge

Newton Mayenge's Jim Chones gets an emotional stint in Season 2 of Winning Time, being traded away from the Lakers to the Washington Bullets after the disappointing 1980-1981 season.

While the series shows Chones as being angry with the Lakers over the move, even storming into Coach Westhead's office and cursing out management, Mayenge's real-life counterpart was more saddened by the news before finding some comfort in the move.

Mayenge's biggest project had him in an uncredited role in 2015's Straight Outta Compton.

33.) Sean Patrick Small - Larry Bird

Sean Patrick Small, Larry Bird
Sean Patrick Small

Sean Patrick Small gives Magic his true on-court rival as he plays Boston Celtics legend Larry Bird, a 12-time All-Star and three-time NBA champion who sees plenty of battles against the Lakers throughout the 1980s.

Bird is much more averted to the spotlight than Magic, preferring his beer and Indiana living while he looks to trash-talk opponents and win as much as possible on the court. He and Magic also continue a rivalry that started in college, with Johnson's Michigan State and Bird's Indiana State meeting in the NCAA championship in 1979 before the Lakers and Celtics' rivalry is renewed.

Winning Time is Small's biggest role to date, with a number of other smaller appearances in short films prior to this.

34.) Max E. Williams - Jack Nicholson

Max E. Williams, Jack Nicholson
Max E. Williams

Max E. Williams embodies yet another real-world icon in Academy Award-winning actor Jack Nicholson, who is also known as arguably the Lakers' biggest fan in franchise history.

Nicholson has been a court-side regular at Laker games since 1970, with Williams starting to bring the acting legend to life in Winning Time starting in the second half of Season 1.

Other projects on Williams' resume include Agents of SHIELD, Bosch, Bullet in the Face, and the Red Dead Redemption video game.

Other Stars in Winning Time

Season 1 of Winning Time also features a number of big names who haven't been seen in Season 2, some of them confirmed to not be returning.

Oscar-winner Sally Field plays Jerry Buss' mother, Jessie, throughout Season 1 before she passes away near the end of the season.

Ant-Man actor Wood Harris takes on another Lakers player in Spencer Haywood, a backup center who spends much of Season 1 battling drug issues before he's sent home.

Comedy icon and Hangover star Mike Epps also joins this series in Season 1 as he portrays real-world comedy legend Richard Pryor.

The first two seasons of Winning Time are available to stream on Max, with new episodes premiering on Sundays at 9 p.m. ET.

- About The Author: Richard Nebens
Richard Nebens joined The Direct in March 2020, now serving as the site's Senior Writer and also working as an assistant editor and content creator. He started his journalism career as a hobby in 2019 and is passionate about sharing news and stories from the entertainment industry, especially comic book movies, comedy, and sci-fi. Richard looks to expand his knowledge about movies and TV every day, and he is eager to stay locked into the latest releases and breaking news at every opportunity.