In Reunited, Awards Insider hosts a conversation between two Emmy contenders who have collaborated on a previous project. Today, we speak with Jesse Plemons, who stars in Love & Death, and Molly Shannon, who appears in The Other Two and guest-hosted Saturday Night Live this season. They previously worked together in the 2016 independent film Other People.

Other People may have been a modest movie, but for most everyone involved, it represented a kind of career breakthrough. For writer-director Chris Kelly, the semi-autobiographical piece about an adult son who returns to his small hometown to help care for his mother after her cancer diagnosis, marked an auspicious debut feature before he went on to co-create Max’s The Other Two. For stars Jesse Plemons and Molly Shannon, the project offered rare opportunities for, respectively, a leading role and a dramatic showcase. Plemons earned a Spirit Award nomination for best male lead, while Shannon memorably accepted the trophy for best supporting female. 

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It’s seven years later, and the two are in the prime of their careers—Plemons in a richly dramatic key on Max’s limited series Love & Death, about the death of Betty Gore (Lily Rabe) at the hands of Candy Montgomery (Elizabeth Olsen), and Saturday Night Live alum Shannon at her funniest in Kelly’s The Other Two, playing the uber-famous mother of adult children desperately trying to break into show business. Much has happened in both of their careers since they first met, so there’s plenty to catch up on. We get into all that—before ending with Plemons and Shannon comparing notes on their favorite Bravo shows. 

Vanity Fair: What were your first impressions of each other?

Molly Shannon: Jesse and I just clicked right away. He was so easy to talk to. He's just so genuine and down-to-earth and thoughtful and very observant. I worked with Jesse before he was with Kirsten [Dunst], which is so wild—I was friendly with Kirsten through my friend Sofia Coppola before Jesse and Kirsten were ever together. Can you believe that? It's just wild how life works. And I was so happy for Kirsten. I was like, “Oh my God, that makes perfect sense.” 

Jesse Plemons: We met at some little coffee shop on the East side—one of those instant, “All right, we could sit here and chat for hours.” I felt the exact same way about you. There's no pretense, no air, so genuine and so easy to talk to and yeah, you’re a great storyteller. And no matter how interesting what you say is, Molly always makes you feel like what you said was in fact interesting. [Laughs]

How did you first discuss working together on Other People?

Shannon: Jesse and I are both really into acting, and we were comparing some notes about some previous teachers and just talking about that. We had the same opinions about some types of teaching. That's all I'll say. [Laughs] We bonded over that, and it's actually a very intimate topic—it's a funny thing to be talking about acting technique when you're in a scene in this intimate way, using some of those techniques that you've learned. 

Plemons: And I had no idea that in your early days, you were mainly focused on theater. I think of shows in your range. You have this amazing handle on dramatic stuff, and then the other side of your training is like SNL. It was so much fun to work with you because of that. We talked a lot about there not being one way. I shy away from any dogma that is very rigid and take things from whatever's inspiring.

Shannon: Exactly. Way before I met Jesse or anything we were talking about, I remember taking a class in in LA actually. It was not good. If you stood up to the teacher, it was like a very, “Don't do that.” And it was a very popular class. I just remember being like, “I don't like this. This feels too cult-y to me.”

Jesse, am I right that you had watched Molly on SNL back when she was a cast member? 

Plemons: Yes, that was my introduction to Saturday Night Live. I was of the age where my parents finally said, “Okay, you can watch.” Doesn't get much better than that era. I'm sure I'm not alone in feeling like this, but when I met her, it's like—I don't know, such a part of very formative years and especially films or anything where you feel like your parents are like, “It's a privilege to get to watch this.” That was my introduction to her.

Shannon: That's so sweet. Oh my God.

I’m interested in what you guys were saying about bringing technique to your actual work together, because it's a very intimate movie, and sometimes quite devastating. How did you find playing scenes as mother and son, connecting in a way that really had to translate as incredibly naturalistic and believable?

Shannon: Yeah, you're right. It was really intimate. We had a scene early on where we're chatting in bed and he's just worried about me. Remember that scene, Jesse? We did that really early on. And it had to be this very natural feeling, but I don't know, it just felt so easy. I think Jesse is one of our greatest actors, and so for me, it was just such a pleasure. We did have a scene at the end too, that I remember, where I was really sick and could barely speak. That was definitely harder. But the whole thing was just a wonderful experience. It's one of my favorite experiences ever, shooting Other People with Jesse.

Plemons: When I was younger, I think I put so much pressure on myself. I've gotten better at managing that, but with this movie, there was this weight on set, knowing that these [were] moments we were recreating from Chris [Kelly]’s actual life and relationship with his mother. There was just a feeling during some scenes that was really powerful and you could just feel in the room. I didn't realize it, but I was going through all of the same thoughts as the character I was playing, thinking, “God, I'm messing this all up. This is Chris's life.” I was in my head for some of it, and was, at times, kind of a head case. I was isolating myself sometimes. And I was like, “God, am I selfish?”

Molly, this was a major dramatic role for you. Did you feel any of the kind of pressure that Jesse was talking about?

Shannon: I think I was just more really excited. I've never had an opportunity like that before, dramatically. So I just felt excited.

Plemons: It was so honest. The script had a shade in the grieving process that you don't get to see very often. It's not just one thing. It's sometimes surreal and absurd and really darkly funny. And there's a whole range, which you only know if you've been through it. Chris was able to put all of that into it.

Shannon: Humor and sadness, everything. 

Molly, your Spirit Awards speech is one of the most joyous awards season moments I've ever seen live.

Shannon: [Laughs] I decided to throw “Superstar” in at the end. Nobody told me to do that. I was just like, “If I win, this will be so perfect.” I was just so excited. Those speeches are hard. I’m always so impressed with people that get up and do that because I think it's very difficult.

Plemons: I was there. Oh my God. The best moment by far of the night.

What has it been like to work with Chris on The Other Two, continuing your collaboration together? 

Shannon: He'll still write these emotionally dramatic scenes that are also hilarious. You play the emotion like you would a very serious, dramatic actor, but then he writes the greatest jokes that are like gifts from God. It's my favorite combo. I love working with Chris. He's just the greatest. In the beginning, I never even watched the episodes because I just wasn't worried at all. I was like, “Oh, I know it's going to be great.” It is different from the movie because the movie was a contained, certain amount of days. It begins and it ends. TV is harder. It goes on and on and on, and it's really like a marathon and you have to pace yourself.For Chris and Sarah [Schneider] who run the show, direct episodes, edit it, do everything, it is really hard. I just have so much respect for what they do and how hard they work. That's a really hard job. Don't you feel that way, Jesse?

Plemons: I can't imagine, when you actually think about the workload, running a show like that. But I think there's also a flip side of it,. When I was doing Friday Night Lights, we shot so fast, but that was built into the show. It was all handheld and we didn't do any rehearsals or any of that. And we're just kind of flying by the seat of our pants. You can get overwhelmed, but there's another thing that sometimes happens where you don't have the time to overthink things. It can kind of be a benefit. Other People felt very fast too.

Shannon: So many actors get in the car after they shoot—I don't know if you do this, Jesse—and they'll redo the scene in their heads so much better by themselves alone in the car. [Plemons nods] They'll go through it like, “Oh, I should've done it like that!”

Jesse, in Love & Death you’re playing another real-life based character, but in a very different key—this being a kind of true-crime tale. How does the preparation differ? Did you still feel that pressure on yourself? 

Plemons: I didn't feel the pressure, as far as the characterization or any of that. I mean, the book was really, really helpful because it goes more in depth into all of their upbringings and how the characters met and all that. Having kids makes things harder in some ways, in terms of just being away, but something shifts in your brain where it's like you don't have the mental space to do the same kind of spinning. It kind of simplifies things in some ways. I've gotten better at what I was talking about earlier. And it was just a really fun show because of how crazy the tone shifts.

Shannon: That was really interesting. I found the whole story of your character so interesting too, in the end, when they say what happened and how he remarried and his kids were taken care of by the grandparents. I really liked that [Elizabeth Olsen’s Candy] was like, “I really want to have an affair with you.” And he's more passive. You played it so well, Jesse. I had not read the book, so for somebody like me, I was like, “Oh my God, this is so interesting.” My daughter and I loved it. We watched it really fast. 

Then [Candy] kept taking those pills. As a matter of fact, this is so funny—I watch Vanderpump Rules. There was a cheating scandal, and I think Andy Cohen said he thinks one of the girls in the cheating scandal might have taken something to make herself calm for the reunion. And so it reminded me of Love & Death because people were wondering why she wasn't very reactive.

Plemons: Should I watch this show, Vanderpump Rules?

Shannon: Jesse! I think you should watch it with Kirsten. Just watch this season because as far as reality goes, it delivers times 100, and it's not hard to just catch up. I would say just watch this last season and you will not be disappointed.

Plemons: I got pretty obsessed with Below Deck.

Shannon: People really like that show. Don't they pay people to go on the boat? You can bring your friends or whatever, right?

Plemons: They must.

Shannon: It's something like that where they get a fee, almost like reality actors, and they can get their friends. I don't know. I thought it was something like that, but what do I know?

Molly, this season on The Other Two, your character has had to navigate fame in a particularly intense way. Did you relate to that story line at all? Curious for both of you how you’ve handled being in the public eye, even since the movie you made together.

Shannon: Yes. When I was shooting The Other Two, I fly back and forth all the time, so I know all the airline stewardesses and they're always like “Ah!” And they'll sit down and talk to me. Sometimes I have to work and memorize my lines. I'll be like, Oh my gosh, thank you. Okay, I got to work now.” I try to be friendly. Pat, my character, of course, has alien-level fame, like Oprah-level. But I think that when you go out in public, you have to be the mayor. “Hello!” I happen to be an extrovert, so I don't mind talking to strangers. But if you're more of an introvert, which a lot of actors are, it's interesting, because people really come up to you a lot. 

You learn a lot about people and behaviors. It's almost like a social study. I had a woman come up to me at a party. She came over and I had a glazed over look of—I thought she was a fan. She was like, “You don't remember me.” That was her intro. And I was like, “Oh God, I'm sorry.” And then it was actually somebody I knew, but I hadn't seen them for 25 years. I don't know if you've experienced this, Jesse, but people will be like, “I went to school with Jesse. Jesse's my good friend. Remember me?” And you find out it was like 20 years ago and you might be bigger in their head. 

Plemons: I agree. A lot of it is some sort of a social experiment because you just meet more people, and so you do learn a lot, and you meet people coming up to you with something very specific. It's a double-edged sword, but most of the time everyone's nice. And yeah, you learn a lot about human behavior.

What's a kind of role you would love to see the other in that you haven't yet?

Plemons: I don't know why this popped into my head, probably, because you met Kirsten on Marie Antoinette. I would love to see you play some tyrannical, evil, funny queen. Kind of Olivia Colman. 

Shannon: Do you know that that's exactly what I would like to do? I would love to play that kind of part. So thank you. Well, Jesse does everything, so I'm like, “What hasn't he done?” Hold on, let me think. This is very serious. [Long beat] Oh, a musical that's really silly and broad!

Plemons: I love it.

This interview has been edited and condensed.