The latest hit series from Winning Time: The Rise of the Lakers Dynasty, which tells the story of how the Los Angeles Lakers became a powerhouse during the '80s. Their "Showtime" brand of basketball basically became a mix of sports and incredible entertainment with celebrities at every game.
That means the series must recreate some iconic figures in sports and Hollywood history. They've done a good job so far thanks to the impressive cast who take on these important roles. Of note, some main actors like Quincy Isaiah (Magic Johnson) and Solomon Hughes (Kareem Abdul-Jabbar) don't have enough in their filmography to be listed here.
John C. Reilly - For Love Of The Game (1999)
Stream On Tubi TV
The most prominent character of the series outside of the guys on the basketball court is Jerry Buss. The legendary figure is the person who decided to purchase the Lakers and turn them from runner-ups into a championship dynasty.
The visionary man is played by John C. Reilly. Although Reilly is most known for comedy, he's no stranger to dramas. A good place to check him out is For Love of the Game as he plays Gus Sinski, a baseball catcher playing during a perfect game. The overlooked film is directed by Sam Raimi and gives you a look at Reilly in a sports role.
Jason Clarke - Chappaquiddick (2017)
Stream On Hulu
Portraying a real person can be difficult, especially when they're well known. That's certainly the case with Jerry West, one of the greatest basketball players in history and the guy whose silhouette is used on the iconic NBA logo.
By the era of Winning Time, West is done as a player and now is the volatile Lakers coach who loathes losing. He's played by veteran actor Jason Clarke, who has taken roles as real people before, including when Chappaquiddick, which details the famous Chappaquiddick Incident. Clarke's work was well received.
Gabby Hoffmann - C'Mon C'Mon (2021)
Rent On Vudu
If there's one character who the audience can quickly gravitate towards in of likability, it's Claire Rothman. She's someone who works in the Lakers office and must deal with being overlooked and things like sexual harassment that was all too prominent in the '80s.
Rothman sides with Jerry Buss and seems like she'll play a big role going forward. The talented Gabby Hoffmann takes on the character and you can see her in the critically-acclaimed C'mon C'mon as Viv, the sister of Joaquin Phoenix's Johnny. The performance earned her a Gotham Independent Film Awards nomination.
Hadley Robinson - Moxie (2021)
Stream On Netflix
There are so many impressive female actors on the rise in Hollywood right now and among them is Hadley Robinson. She had some small roles before landing a spot on Moxie last year.
Moxie follows Vivian (Robinson), a teen who starts a magazine to empower girls in her school. In Winning Time, she plays a young Jeanie Buss who is an important figure as she is currently a controlling owner and President of the Lakers. Seeing her early days with the team will be interesting.
DeVaughn Nixon - Marvel's Runaways (2017-2019)
Stream On Disney+ & Hulu
If there's one piece of casting that stood out to those who know about it, it was DeVaughn Nixon being brought on. He will be playing Lakers point guard Norm Nixon, a man who has a tense relationship with Magic Johnson since they play the same position.
The interesting thing about it is that Marvel's Runaways as Darius Davis.
Sally Field - The Amazing Spider-Man (2012)
Stream On TNT, TBS, & TruTV
Another actor with a ton of credentials is Sally Field. In fact, she has two Oscars, two Golden Globes, and three Emmys to her name among many other accolades. A lot of modern fans will likely know her from The Amazing Spider-Man movies.
There, she portrayed the likable Aunt May and her relationship with Peter Parker was one of the highlights of the films. Field rounds out the Buss family as she plays Jessie, mother to Jerry and grandmother to Jeanie. It's unclear how much she'll show up so far though.
Rachel Hilson - Love, Victor (2020-Present)
Stream On Hulu
Yet another talented actress on the rise is Rachel Hilson. She might not be a household name but she has had standout performances in shows like Love, Victor.
The show is a spin-off of the Love, Simon film and it sees Hilson play Mia, the ex-girlfriend of the titular Victor before he comes out publicly as gay. In Winning Time, she'll be portraying Cindy Day, the girlfriend of Magic Johnson.
Jason Segel - How I Met Your Mother (2005-2014)
Stream On Hulu & Prime
One of the most recognizable names on the cast list is certainly Jason Segel. The actor has kind of popped up everywhere over the years but most people still know him from he played Marshall Eriksen for nine seasons.
Not only does it show his great acting chops but there's also a running joke about his past as a basketball player who was really bad at defense, giving it some connection here. He plays Paul Westhead, a veteran player on the Lakers who wins a championship with them.
Sarah Ramos - Parenthood (2010-2015)
Stream On Peacock, Hulu, & The Roku Channel
You might not know who Sarah Ramos is but there's no questioning her talent. For one thing, she directed an episode of Marvel's 616 for Disney+ on top of her acting credits. Ramos has already appeared on Winning Time as Cheryl Pistono, the girlfriend of Kareem Abdul-Jabbar.
Easily, her biggest role was as Haddie Braverman on Parenthood, portraying her from a young high school student all the way through being in college as a guest star in late seasons. Ramos was one of the best performers on the show, so seeing her on this series should be great.
Adrien Brody - Peaky Blinders (2013-Present)
Stream On Netflix
Another huge name in the cast is Adrien Brody and audiences everywhere are excited to see him take on one of the most iconic roles of the series. He will be playing a young Pat Riley, a legendary coach who helped guide the Lakers (and later the Heat) to multiple champions.
Getting to see Brody embody Riley will be a blast and he certainly looks the part. There are so many great roles to recognize Brody from but his best work on TV is possibly his run as the villainous Luca Changretta in Peaky Blinders.