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Jason Segel And Solomon Hughes On ‘Winning Time,’ Power Struggles, And Their Gams

If you’ve been keeping up with Winning Time (which runs Sundays at 9PM on HBO) you know that things reached a head last week between burgeoning icon Magic Johnson and Iccarus in a sport coat head coach Paul Westhead over Johnson’s ill fit with “The System” playbook and Westhead’s view of the hierarchy. A trade demand was issued and now both men are set to see who has more sway with team owner Jerry Buss.

If you know basketball history on a base level, you know which of these two big personalities and talents is about to have a bad day in this next episode. But outside of this standing as an interesting point in the history of the Showtime-era Lakers, it also connects to this moment in sports culture. In the mid-80s, Magic Johnson was a trailblazer. Now, most athletes are paid more than the coaches and GMs who draw up the game plan and build the rosters and some superstars have a seat at the table when it comes to personnel moves. It’s fascinating watching Magic come into his power like this, but it’s also really interesting watching everyone else kinda freak out when he’s consulted on trades or wins a power struggle.

Actor Jason Segel is a big part of that palpable freakout as his character, Lakers coach Paul Westhead, tries like hell to keep the status quo, using his players as pawns in his grand scheme whether they like it or not. And forget about letting a player dictate who is on the roster. It goes against everything he stands for, especially as he cultivates an image of himself as an outside-the-box mastermind.

Before that image gets tested, though, we spoke with Segel and with Solomon Hughes, the actor who plays Kareem Abdul Jabbar, a legend from a different era who is often caught in conflict with Johnson’s brand of office politics and on-court play. In the conversation, which took place before the SAG strike, we discussed Segel’s insights on Westhead’s ego bloom, Hughes’ thoughts on Kareem and Westhead’s alliance against Magic, and the wonderful world of short shorts, bad wigs, whether we can make the word “gams” come out of retirement, and Segel’s pitch to come back in the future to play Phil Jackson.

What were you most looking forward to playing with these characters specifically, this season?

Solomon Hughes: Just further exploration of these great people’s lives, right? Beyond just what we saw on the basketball court, the ups and the downs, the tensions, the things that they were dealing with off the court. I think they all really kind of build on this incredible story of what they were able to accomplish as a group for such a long period of time.

Jason Segel: I knew that Paul Westhead was going to show up a little bit sassy this year and that was exciting for me.

It’s obviously not a documentary, it takes some liberties with the Paul Westhead character this season. Sassy is a word you could use. There are definitely some elements of his personality that come through in this season that someone might not love if that was them being portrayed. Any apprehension on your part about that?

Segel: No, I feel as though no human being would want to see themselves portrayed on screen in all of their full colors. So even if it was completely accurate, even if it was dead on accurate… I think we’re uncomfortable with ourselves and we never get to see ourselves clearly. That’s one of the weird things about being yourself, and so that is an unwinnable test. I think that what I always try to do when I’m acting whether a character is real or not real is I try to play them as though they’re me and I try to love them.

And so really early on I decided that Paul Westhead was a Shakespearean scholar and this was heightened reality and I was going to try to draw a Shakespearean arc and hope that as long as I loved the character and tried to be honest about each and every scene that it was going to be okay. And I really hope that’s true and if it’s not, I’m certainly sorry. I would hate to hurt anybody’s feelings, but I tried to do right by the story we were trying to draw, especially as an archetype.

I’m curious about what it is you think drove that conflict and at times rivalry between Westhead and Pat Riley? That need for Paul to put Pat in his place essentially. What it was about the characters that kind of motivated that conflict?

Segel: I think that Westhead is battling some severe imposter syndrome because he is not getting the credit he thinks he deserves for season one’s championship because it’s under the shadow of McKinney getting injured. And I think that probably there is a subconscious sense that Pat Riley is a better basketball mind than he is, and so he is sort of trapped in this position of the guy before him is considered a better basketball mind and he’s going to get found out real soon and he’s going to go back to where he came from.

Solomon, the alliance between Kareem and Paul, I wouldn’t say it’s buddy-buddy at all times, but it definitely feels like there’s an alliance there. Are they unified because both characters aren’t necessarily fully enamored with Magic?

Hughes: Well, I think it’s more that there’s familiarity. (They’re from) similar eras in terms of their perspectives on the game. I think Kareem, the Real Kareem, talks about his reverence for his coaches, John Wooden, et cetera. And to see that balance upended, I think it’s new and I think it speaks to a lot of the changes that were happening in the game in terms of just its visibility in terms of its star power. And so I think whenever familiarity is disturbed, interesting things happen.

You’re older than the other players, the other actors that are playing players. Is that helpful for you in terms of feeling somewhat, I mean, I get exasperated by younger writers sometimes. I’m sure you get a little exasperated from time to time by some of these 25-year-olds running around jumping and bouncing all over the place. Does that help to inform the portrayal?

Hughes: Yeah, but in addition to that, I remember playing being a senior and how you deal with incoming freshmen that might have a lot of talent, but not a ton of maturity, those dynamics. It was helpful to experience that. But yeah, I think for sure, I mean you’re looking at life a little bit differently for sure, and I think all that helps.

Jason, the mullet was on point. I’m curious how delighted you were to see yourself with that look and also the wardrobe. Some of those choices are pretty, again, I think sassy is the word of the day on those. Can you talk a little about bringing the character to life in his glow-up phase when he’s trying to embrace the Hollywood thing a little bit?

Segel: I made a decision, which is, in season one I was wearing a wig and I would be doing acting that I was really proud of and then I would turn and I would see a mirror and I would think, oh, it doesn’t matter. It doesn’t matter. I’m wearing this wig.

Oh, so is that real mullet? That was all you this year?

Segel: Season one was a wig and then I decided after that if we do a season two, I’m using my own hair. And so I told them on Shrinking that I was going to be growing my hair out during the season. And so they were very kind and let me grow my hair out. So it was a lot more comfortable to be working with my own hair.

It’s a beautiful mullet. I’m surprised you didn’t keep it. You didn’t want to just stick with it?

Segel: Well, it’s starting (again). Look at this.

Yeah, it’s a little there.

Segel: It’s a little bit, yeah. And this is not in prep for anything. This is just a strike hairdo.

Yeah, that’s right. In terms of the name for “The System” (Westhead’s on-court strategy), any thoughts on an alternate name? Because it is a pretty bad name.

Segel: I stand by the name of the system. Maybe it’s because I have to, but I think it is a very definitive and grandiose name. This is The System.

There’s no other like it.

Segel: People are focusing too much on “System” and not enough on “The,” which is what’s doing the heavy lifting.

Hughes: Timing is everything.

Segel: (Laughs) Yes.

Solomon, I don’t want to leave you out of the wardrobe conversation with the shorts of the era. Is there ever a moment where it’s like, can we just maybe extend it just a little bit? It might be just a little too short. Is that a thought that you ever expressed to the wardrobe department?

Hughes: I’m sure that was one of a number of conversations I had with the wardrobe department. I mean, I loved the gear, don’t get me wrong, but yeah, the shorts took some getting used to for sure. You had to wear tighty whities underneath. You couldn’t wear biker shorts, anything like that. So yeah, that was interesting. But the other thing is everybody else is wearing them, so there’s this sense of normalcy and you don’t feel as exposed. Everybody’s gams are just out there.

Segel: That’s how you know we’re old, by the way. He just said gams.

Hughes: I feel like the young folk are bringing it back. They’re bringing it back.

Jumping back to hair, Kareem’s more fully balding era, is that something you’re looking forward to or dreading?

Hughes: If that means that we get to work together again?

So that’s the price you’ll pay. But Jason, you won’t obviously be on the show at that point.

Segel: I may come back if this show goes long enough. I’m going to lobby to play Phil Jackson. I’ll wait it out, the timing will line up. I’ve done the math. (Laughs)

Or John Paxson, and then you can get in those short shorts. You get your gams out.

Segel: Yes. There you go.

New episodes of ‘Winning Time’ air at 9PM ET on HBO and on MAX