Jason Segel Talks Transforming Into Paul Westhead for ‘Winning Time’

Jason Segel
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[Warning: The below contains spoilers from Season 1, Episode 6, “Memento Mori”] Winning Time: The Rise of the Lakers Dynasty

Out of tragedy comes opportunity for Jason Segel’s Paul Westhead on Winning Time: The Rise of the Lakers Dynasty. The Los Angeles assistant coach finds himself stepping in for head coach Jack McKinney (Tracy Letts), who is clinging to life in an ICU bed after a devastating bicycle accident.

With the schedule in full swing and the NBA team’s hope to keep McKinney’s health status out of the headlines, Westhead is thrust into the spotlight as the interim man in charge. The proverbial student must now become the teacher while also managing the clash of personalities between Magic Johnson (Quincy Isaiah) and Kareem Abdul-Jabbar (Solomon Hughes). Not to mention owner Dr. Jerry Buss (John C. Reilly) putting the pressure on Westhead to win with literally everything on the line. Who said basketball was just a game?

Here Segel sits down to go into Westhead’s evolution and gradual transformation.

Given your basketball background in high school as “Dr. Dunk” and winning a slam dunk competition, did going to set bring back memories?

Jason Segel: It actually does bring back some really great, really fond memories. It also brings back the really intelligent level of fear that someone is going to ask me to do anything resembling play like that ever again.

Did you have any playtime on the court with the cast?

Honestly, I tried to stay as far away from that as possible. I did not want to be exposed as a fraud. I let them believe whatever they wanted to believe about my athletic ability. I would just sit and listen to my iPod.

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In the last episode, Paul is really put under tremendous pressure in a very short timeframe. Here a close friend and mentor in the hospital fighting for his life, but he also feels this obligation to keep everything he worked for on track.

I think not believing in yourself is a really relatable thing. I think when you don’t believe in yourself the nightmare scenario is you are forced to be a leader. I really wanted to set that up as the blank canvas. In episodes 4 and 5, Paul Westhead is sort of the comic relief in Winning Time. So, when that bicycle accident happens and I’m made head coach essentially, I wanted the audience to feel the same way Paul Westhead felt, which is, “Oh no! This is not going to go well.” To see somebody succeed here, I think is really inspirational.

For a lot of actors on set, this is their first big break. How was it working with them?

It is honestly the joy of the whole show. Watching these men. There is a learning curve for all this stuff. I think when you have the exuberance of youth and the confidence and do these things that have taken me 15 years to wrap my head around. They’ve done this within a few episodes…To watch Quincy, Solomon, and all these guys, episode by episode, they’re owning the performances more. We would talk about it. Tracy, Adrien [Brody], and I would talk about it. We were watching a lot of these scenes as the coaches.

You are able to show different sides within this role. In the first episodes you mention taking a more comedic tone, but there are some raw and emotional scenes with Paul in the hospital as the weight of the world is felt on his shoulders.

To me, really great comedy is just layering it on top of drama. It needs to be under there for the comedy to be good. It’s the same skillsets. I think over the past six or seven years after How I Met Your Mother ended, I made some real conscious choices to be around people I admire. I wanted to do projects I was scared of…This show is perfect for me because it’s the synthesis of all these different tools I’ve sharpened from my backpack.

'Winning Time': Tracy Letts Talks Shining Light on Coach Jack McKinneySee Also

'Winning Time': Tracy Letts Talks Shining Light on Coach Jack McKinney

Letts unpacks McKinney’s arch on the HBO show and the importance of giving this unsung hero his due.

The show really transports you into the late 1970s into the 1980s. That goes for the hair and wardrobe. How was it for you to step back to that time?

For me, it was largely humiliating [laughs]. Every time I had to step out of my trailer in these tiny shorts, I just felt like, “Oh, now I’m going to go do acting.” I would hope and pray I didn’t pass the mirror at any moment when I needed to feel confident.

How would you describe Paul’s evolution heading into the back half of the season?

He undergoes this transformation and goes through hell to get there. He gets sick. He gets scared. He is vulnerable. Slowly, he has to learn how to stand up for himself and say no. He has to learn to set boundaries and has to learn to stand up and speak confidently to people he knows are in a lot of ways better than him. It was a really cool part to play.

What was it like for you to have this story of the Lakers told?

There was a moment in my life when I was really passionate about playing basketball in high school and really passionate about the acting I was doing. Even though, I was literally acting secretly because I was too embarrassed to tell my basketball friends. I definitely did feel a special synthesis happening where it was, “Look where you ended up. Funny how it all goes.”

You’ve come full circle in that sense.

That’s right.

Tracy Letts and Jason Segal

Warrick Page/HBO

The news came out that Winning Time was renewed for season 2. How is it knowing the story will continue?

This is a total dream job. I said to the young guys on the team, “I know for some of you this is really early on in your career. It doesn’t get better than this. Enjoy every minute.” When they announced season 2, I felt really lucky I get to do this for another year. Especially, with the friends, I got to make. We’re making art and getting along and it’s turning out cool. It’s pretty rare.

What do you hope is explored next?

Because it is based on history, you kind of know what will happen with the Lakers. But what will happen with Westhead? A guy right now trying to wrestle with his own ego, which he hasn’t had to do before because his ego is so deflated. There are a lot of players, especially Magic Johnson, who have big egos of their own. You’re going to watch this historic power struggle go on between Magic and Westhead.

Winning Time: The Rise of the Lakers Dynasty, Sundays, 9/8c, HBO

Catch episodes also on HBO Max.