Justine Lupe on Willa, the Sex Worker Tied Up in ‘Succession’

In the dark and twisted world of Succession, where alliances shift on a dime, everyone is always lying, and no one isn’t expendable, it’s tough to identify who, if anyone, is the most morally upright character in the show. But Willa (Justine Lupe), the high-end sex worker-turned-playwright-turned-political-wife, comes close.

At the start of the series, Willa is an outsider who serves as a proxy for the audience, a fish-out-of-water trying to navigate the choppy waters of the Roy family. As a high-end escort hired by Connor Roy (Alan Ruck), Logan’s buffoonish, goat-like failson, their relationship initially starts out as purely transactional, with Connor offering to fund Willa’s theatrical ambitions. Yet as Connor starts falling for her, and Willa becomes more deeply enmeshed with the Roy family, their dynamic evolves into something more complex and weirdly sweet. By the time Connor asks Willa moments before their wedding whether she’s just marrying him for his money, and she responds in the affirmative while confirming her loyalty to him as well, it’s clear that in many ways, they have the most honest and healthy relationship on the show.

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Played by Lupe with wide-eyed, coltish energy, Willa has become a Succession fan favorite, known as much for her occasional yet sparkling bon mots — to date, she is perhaps the only Succession character who has stunned Marcia (Hiam Abbass) into silence — as her savvy in getting the bag. Rolling Stone chatted with Lupe about Willa’s killer wardrobe, who got drunkest at the Succession wrap party, and Alan Ruck’s extremely Connor-esque moment related to that huge Episode Three twist.

This interview has been edited and condensed for clarity.

Willa has evolved a lot over the past four seasons. I’m curious, what was the description for the character like when you initially auditioned?
Oh my gosh, it was six years ago. So I don’t actually remember what the character description was. I knew that she was a high-end escort. So I knew that she was hired. They gave me one scene that was a breakup scene between Connor and Willa, and it was in a bedroom. That was the only information I had. [I] auditioned just with [casting directors] Doug Aibel and Henry Russell, and it was a tape that they ended up sending off. I remember seeing it was for HBO and that Adam McKay was producing it and big names were on it, so I thought, “OK, I probably won’t get this.” I was so pleasantly surprised I got it. But I didn’t ever meet Alan until the day that we met on set in the hospital [after Logan has a stroke in the first season].

What was that like, to act with Alan for the first time? It seems like you guys have a really fun dynamic.
I remember he was immediately incredibly warm and easy to talk to. The first scenes that we did together on set, they were these really long night shoots, and it was a lot of one-on-one time. We were starting nights at 8:00 and going all the way into three or four in the morning. It’s not the easiest first meet, doing an overnight shoot with someone that you’ve never met before for hours on end. But I just remember him being so warm and kind and interesting and interested. I immediately really liked him and felt really at ease with him.

I spoke with Dagmara [Domińczyk, who plays Karolina on Succession] last week and she said Alan Ruck was the funniest person on the Succession cast text thread. Do you agree with that assessment?
Alan is the funniest. He also feels like the dad of the text chain. There’s a really funny story about the text chain, which is that Jesse [Armstrong, the creator of Succession] let a core group of people know about Logan’s passing in the first table read. And the text chain has way more people than just the main series regulars. There were a lot of people that hadn’t found out yet, and we were supposed to keep very hush-hush about the whole thing. And there was a point where Alan wrote on the thing, like, “Oh, Episode Three is going to be so, so sad.” He pretty much gave him a little bit of a leak on this text chain. And then I sent him a separate chat text individually, like, “Alan, you’re not supposed to be telling everyone,” and he’s like, “Oh, shit, oh, man, I’m too comfortable in this chain.” And then I was like, “Don’t worry, I’ll flood the chain so that nobody sees that.” I started writing random things on the group chat to get his text out of the way so that nobody would see it. I remember like three people texting me like, “What’s the deal with you and Alan? You guys are pretty manic on this chain.”

That’s very Connor.
I know.

I was actually rewatching the first season and I didn’t realize that Roman actually mentioned that he introduced them. Did Willa date Roman too? How much did you and Alan discuss Willa’s backstory?
No, I don’t think he necessarily dated Willa. I think he just says, “Yeah, she’s a party girl that likes getting paid by guys to date them.” I kind of imagined that Roman had her in his periphery and they hang out in the same social circles, and that Alan was at a bar one night — I think Alan and I kind of went over this, at the very beginning of us creating the characters — and that we connected and that he made a pass and kind of understood what was going on there, and it just ended up escalating into something that was far more than just Willa’s normal protocols.

I’m curious, did you talk to any sex workers over the course of doing research for this role?
No, no, because it’s a very particular kind of sex work. I did have a friend when I was in my early 20s who did something like this, where she was an artist and a creative and she needed a little bit of extra cash on the side and so she went on dates with guys that would pay her, but I just felt like this wasn’t really in my wheelhouse and to go too far down a road that wasn’t in line with what Willa’s actual experience would have been, I feel like could have led me a little bit off-track.

I saw a TikTok this morning about how there’s some significance to the fact that Willa often wears a black choker, because apparently sex workers during the French Revolution would wear black chokers to mark themselves. Is there any significance to the fact that she wears a black choker?That’s fascinating. I’ve never seen that. No, Michelle [Matland], who’s the costume designer, and I wanted to find a way to continue to keep [Willa’s] artistic sensibility and a little bit of her edge and a little bit of the drama alive in Willa’s wardrobe, while she’s kind of assimilating into this new position of being a presidential candidate’s wife. We wanted to find small ways to kind of keep her in touch with her being an artist. And so we thought that a choker might bring a little bit of her youth into the picture and a little bit of her edge into the picture. Because that is such a major point of kind of attention in their relationship, that she’s with this much older man.

I’m really fascinated by Willa’s wardrobe, because it seems like — and correct me if I’m wrong — that it becomes a lot more high-end over the course of the season. Can you talk about that a bit?We wanted her to start out a little bit bohemian — she’s an artist, she’s in New York, she leans into that aspect of herself quite intensely. So we played around with the Santa Fe kind of version of Willa, the flower dresses, and what would this woman be wearing when she’s not quite like a Roy yet. We wanted her to feel like a black sheep, the difference between her and the rest of the family. That was where we started out, and then we just really wanted to play with, how does this woman progress as she stays with the family? She’s going out with these people that are mega-billionaires, but she also is kind of funky and has a free spirit, so how can we marry those things and keep her essence alive while she’s assimilating into this family that’s very different than where she came from? We wanted to find a way to help her lean into the politician’s wife part of this, as well as keeping a little bit of her sex appeal and her independent nature alive.

It seems like she’s increasingly getting comfortable with her role as trophy wife, like in last week’s episode, when she started interior designing Marcia’s apartment at Logan’s memorial. What was the turning point for her? How did she get to that point, because she was uncomfortable with this role for so long?
I don’t necessarily think that she was so uncomfortable with being with Connor. I think that she’s always had a hard time with the commitment part of it, and the conditions of their relationship have always been kind of ambiguous. She’s always kind of been pushing against his propositions in different degrees. But I never felt like, oh, this woman is having a really hard time being a part of this world. She was willing to have [Connor] spend millions and millions of dollars on her play, you know? So it’s not like she feels uncomfortable with their money.

I don’t think it’s so much that she feels uncomfortable with the money. It just seems like there’s real ambivalence on her part, especially in the beginning of this series, about the relationship, and she also ditches Connor the night before the wedding. Did you guys talk about why she does that? What’s accounting for that ambivalence at that point in time?
In terms of addressing her ambivalence toward the beginning of the series, you see their relationship evolve. It starts out as more of a transactional kind of endeavor, and she was benefiting from the financial benefits of the relationship. But she’s grown to feel real affection for Connor and their relationship has moved in a different direction that I think surprises her. She’s still incredibly independent, and she still has her own ambitions. I think that that also plays into things like with some of the political stuff last year, where she’s on her phone, and she’s writing away. I think she’s incredibly good with boundaries and knowing how much she wants to give. But you also see her step into a new position of protecting him as the series goes on. And I think what happened with the rehearsal dinner is that she had a bit of an existential dilemma where she’s really considering, “I love this person, I care about this person, I’m endeared to this person, I have compassion for this person, I see this person’s trauma and where they’ve come from.” I think she really does believe he’s a good person who really cares about her on top of him being able to financially take care of her. But it’s not the most passionate relationship. And I do feel like there’s a sacrifice there. It’s not what we all imagine the great love story to be for ourselves. My feeling was that she got a little bit drunk and she took off and had an existential moment to process it, and went out and let off some steam and, like, had a real come-to-Jesus moment about what she was doing, and then came back and got into bed.

What was it like for you to shoot the wedding episode? You played a very pivotal role.
I loved that. I was so grateful for that moment. It felt like the first time that both of them were just putting everything onto the table. It was this very vulnerable moment between the two of them where they both said, “This is where I’m coming from,” but also Connor came and said, “I’m scared and this is where I feel vulnerable.” It also feels a little bit cathartic. There’s been this recycled kind of conversation that they’ve been having for four seasons, like, do you want to do this? Do you want to do this? Do you want to do this? And nobody’s quite getting straight to the heart of what’s going on between them. And so it felt like this kind of cathartic landing between the two of them.

She had that big moment, where she says, “I’m with you for your money, but I’m not just with you for your money.” Why do you think she says that? Do you think she truly loves Connor?
Yeah, I do. I do. Is she wildly in love with Connor? No. It’s like, yeah, you offer me security. And also, you’re a good man. And I’m a version of happy with you. I don’t know if it’s just that I’ve lived with Willa and Connor for the last six years, and I’ve seen the little nuances to the way that their relationship has evolved. But I feel more hope about their relationship and more optimism about their relationship than some of the audience does. They’ve got something that’s quite honest and authentic, and they communicate with more compassion than a lot of these other couples in the show communicate with.

I saw that Kieran Culkin say he thought Connor was the most evil character on the show, for entrapping Willa.
I know, I can’t with that. That’s just Kieran being provocative. I think that’s just Kieran being a stinker. I feel like that’s such a reductive way of looking at what happened between these two and I don’t know if Kieran would necessarily in all earnest stand behind that. Maybe I’m wrong. Maybe me and Kieran should have a chat. I just don’t agree.

Do you have a thought as to who the most evil character is?
Let me think about this. I don’t want to just answer impulsively. I feel like Greg is becoming the most sour. Greg is becoming a little rotten. There’s something about watching him just collapse into this guy that’s just kind of gross in the way that he handles things. Even that moment where he’s with Marcia in the last episode [egging on her humiliation of Kerry, Logan’s former assistant and lover] and he’s like, “Oh, look at how disgusting this is, how embarrassing.” It’s just so gnarly. It’s the steepest decline, because the first two seasons, you see him being this endearing, kind of fragile presence. Watching him devolve has been pretty impactful for me.

What were the wrap parties like and who in the cast got the drunkest?
[Laughs] The wrap parties were great. There was so many of them. We had one after our final table read. We had one after our wrap in New York. We had another after the premiere, like a dance party, and the night before Jesse threw this wrap party for the whole crew. We really maxed out our party cards. Everyone loves each other so much, the crew and the cast were all so close, it’s been such a ride. We went through six years of pandemic, not-pandemic, travel, all these kinds of special and also the hard moments together. And so we were all pretty close, so there was a bittersweetness to all of it. Who got the drunkest? I think, honestly, the night of the premiere, I think I got the drunkest. I don’t really drink and I had three drinks and I was really determined to stay to the end. And there was one moment where at the end of the night, my brother, who was my date, was showing me videos that he had taken of us all dancing and he had sent them all in this text to his girlfriend and had written “Justine’s blackout.” There was another one of me like doing pushups on a pillar with Juliana [Canfield, who plays Jess]. It was one of those moments I don’t think he wanted me to see what he’d written. I wasn’t blackout, but I had a fun time that night, for sure.

Can you tell me about the “Call Me Maybe” video from the wrap party [that went viral on Twitter]? It’s probably my favorite thing in existence right now.
The way this all started, there was no dance party and then [Sarah] Snook loves dancing so much — she’s such a free spirit, it’s funny how much different she is than Shiv, she’s got a lot of heart and just no self-consciousness, and I think you see that in her acting for sure — Snook and I love dancing so much that we just started dancing with Juliana. And that song came on and it became like this mosh pit type of thing. And then all of a sudden you see Jesse, who’s the loveliest, kindest, sweetest guy, but is kind of an intimidating figure, come out into the middle of the circle and start dancing. I was like, “This is amazing. My boss is dancing with us.” And then all of a sudden you look over and Brian [Cox]’s right there in the middle and they start hugging in the middle of this, these two incredible figures, and it just felt like this kind of dreamy, cathartic moment.

A lot of people on social media were like, “Where’s Jeremy [Strong]?”
I don’t know where Jeremy was! I think that was toward the end of the night, so maybe he just turned in early. J. [Smith-Cameron, who plays Gerri] was also not there for that, which was a bummer because she’s such a blast, too. So there were a few people that turned in a little bit early, but yeah, I would’ve loved to dance with Jeremy. I wonder if he would have done it.

What can you tell me about how Willa evolves this season? Does she sort of continue to settle into her Melania Trump role?
You know I can’t tell you that.

You can allude.
I’ll just say, she continues to to take the ride with Connor. Whatever he’s gonna gonna go through this season, she’s there. So I feel like that’s the most I can probably say.

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