Austin Winsberg is a little worried about the reaction to this Tuesday’s Zoey’s Extraordinary Playlist.
“I’m starting to get paranoid that everyone’s going to turn on me after that episode,” Winsberg says with a laugh.
This week’s upcoming episode is a big one — Zoey (Jane Levy) continues to mourn her father’s passing all while juggling a promotion at work and her new romance with Max (Skylar Astin). Plus, Zoey also has to balance being a supportive daughter, sister, and friend. And did I mention she can hear people’s thoughts in the form of over-the-top musical numbers? It’s a lot. But episode three proves that any fears of an Extraordinary sophomore slump are completely unfounded. The series continues to be a near-perfect cocktail of profound human emotion and drama blended with genuine comedy featuring performances that reverberate long after each episode ends.
During our conversation, I asked Winsberg how exactly the Zoey team hits the right notes every week and managed to get him to dish on major plot points he has planned for this season.
Episode three, in my opinion, marks the best Zoey has ever been. But, if this interview is any indication, perhaps the best is yet to come.
Awards Daily: We don’t want to spoil anything, but what can you tease about episode three?
Austin Winsberg: What can I tell you? Zoey is having a recurring nightmare, and it’s affecting her ability to sleep. And she’s so troubled by the nightmare that it’s impacting her work. It’s impacting her in her relationships. And it gets worse and worse as the episode goes on.
AD: I wanted to talk about establishing Zoey and Max’s romance. First of all, there’s that really creative love scene at the end of episode two. Talk to me about that, because that is one of the most innovative things I think I’ve ever seen. What was your inspiration for portraying that pivotal moment in that way?
AW: We liked that scene that we did in the season finale last year, where Max was singing a song for her when they were trying to hook up. And we thought that this could be an interesting, funny escalation to that. On top of that, we got excited about the idea of doing one act of the show as just one long scene between the two of them. After the buildup of everything sexual with them, just to live in that moment in real-time with them felt interesting and innovative. And, we liked the idea of going from it being comedic to being sentimental and emotional.
You know, I grew up writing plays and loving theater. We approached it like a one-act play, and we even rehearsed it for two weeks, like a one-act play before we shot it. Everything was thought out within an inch of its life, the choreography, and all of the movements.
AD: I wanted to ask you about season two’s delicate tonal balance —this is something you did very well in season one. But I think season two pushes it a little further. You have a study of profound grief, a romantic comedy, and a workplace comedy satirizing Silicon Valley. There are many different tonal shifts in each episode, yet it’s well balanced and interesting. How do you manage to pull that off each week?
AW: [Laughs] I think that’s always the greatest challenge of the show. And the thing that I am most concerned about is tone, because we vacillate between comedic moments, emotional moments, musical moment. And trying to find the right balance of that is something I talk about every day in the writer’s room. I talked about it with the actors. I talked about it with the directors. We discussed it in the choreography, and it extends to editing. Every step of the way, I’m always trying to be mindful of that. And that’s why it’s such a challenging show to navigate— if it gets too sentimental, it can skew one way. If the musical stuff gets too jokey, it could feel silly. So, trying to make sure that all of those things can coexist in the world is the biggest challenge of the show.
But, it’s also the way that I think life is too. Because we laugh, and then we cry, and hopefully, we sing and dance a little bit. So, I am trying to emulate that to some extent.
I mean, I’d hate for there to be emotional whiplash from scene to scene. Hopefully, when you view it as a whole, you’re encompassing and viewing everything Zoey is going through. And that’s the goal, that every week we can have some degree of emotionality with comedic stuff happening at the same time.
But not every episode is going to be as emotional. Episodes four and five that are coming up, for the most part, are much lighter episodes.
AD: On that note, what can you tell me about season two? What did you hope to accomplish?
AW: From the early days of thinking about season two, I thought about what to do after Mitch’s passing. That storyline was very much the show’s emotional anchor. And I started wondering if we needed to create a new disease of the season or illness of the season to get us through. And to me, something about that felt a little fake or artificial. And I wanted to stay authentic. This show was based on what happened with my own father. So, for me, it was more important to stay in the emotionality of what Zoey is going through. For me, grief was an extended process. I cried for the six months leading up to my dad dying, and I cried for six months after he died. I thought an interesting emotional arc and through-line for the season would be to chart the different phases of Zoey’s grief. And I believe grief is not always a straight line. The arc of the season became about Zoey’s path through recovery, and similarly, Maggie (Mary Steenburgen)’s path to recovery and David (Andrew Leeds)’s path to recovery. The whole family is struggling to deal with it. And we all handle grief differently and approach it in different ways. And we’ll see that coming up with other characters too, but we all have different approaches for that.
So that became the through-line, the emotional arc of Zoey navigating grief throughout the season and the ways in which she recovers, or tries to recover, then relapses, then rises from the ashes. I wanted to go through the spectrum of those feelings.
AD: I think a lot of times in TV and movies, the grief just disappears. That was a concern of mine going into season two. I’m happy you that delved into that and are taking time to explore the nuances of everyone’s experiences.
AD: We need to talk about Max and his arc for season two. I’ve loved what we’ve seen from him so far, and he has an incredible musical number coming up in episode three. Again, exploring the dynamic of Zoey and Max’s relationship through music has been interesting. What can you tell me about what’s coming up for Max in season two?
AW: Yeah, I mean, first of all, I do everything through the prism of what is Zoey going through? What does Zoey need right now? And so Max and her journey continues as they try to navigate what’s next for them after episode three. And how they can be there for each other but also give Zoey the space that she needs to recover.
This is an ongoing journey for them that has different twists and turns. And Max also needs to find ways to protect himself. And Zoey needs to find ways to recover. And some of that means together, and some of that means apart.
AD: One thing that you told me when we first spoke last year is that Andrew Leeds’ character, David, acts sort of like a stand-in for you and your own experiences. You became a father shortly after losing your own. What’s coming up for him? And in what ways have you continued to use your own story as inspiration for his character and others in the show?
AW: [Laughs] That’s funny that I said that before. I would say that David, Max, and Zoey are all extensions of me in some way. I think David is also wrestling with understanding that time is precious and that there are no guarantees. And how do we want to spend the time that we’re here?
By becoming a new father, he now has something new that is important to him. Wanting to be with [his son] will create new complications for him, especially in terms of his job and trying to reassess what he wants to do with his life. I think when a death happens, you can’t help but put things in perspective and say, ‘Am I happy?’ ‘Is this what I want?’ ‘How do I make the most of the time when I’m here?’ And I think that’s what David is going through.
AD: I love that season two has given us a lot more insight into Emily (Alice Lee). What are some of the other characters that you want to explore further? Any other backstories that you could potentially tease for us?
AW: Well, we’re going to see some more with Emily now that we’ve seen her sister, and some of the emotional stuff that Emily is going through. We meet Max’s father in episode five. We certainly do a deep dive into some very real-world issues with Simon (John Clarence Stewart) in episode five and six in particular. Episode six is an episode that I’m particularly proud of—dealing with systemic racism in the workspace. And it’s something that’s very prevalent in Silicon Valley.
As the Black Lives Matter discussions are taking place, we also talked about it in the writer’s room. It felt like something that we could explore in an interesting way on our show.
Who else do we continue to do deep dives in and explore? We do some romantic stuff for Leif (Michael Thomas Grant) and Tobin (Kapil Talwalkar), respectively.
Every one of these characters— for Mo (Alex Newell)—I’m always looking for ways to add dimension and go more in-depth and understand their issues. And we see Maggie back out in the world, too. We see Maggie working on a new house for multiple episodes.
AD: Mary is doing such an incredible job on the show! Before I let you go, Is there anything else you wanted to mention that we haven’t discussed?
AW: I mean, the only thing I would say is that in general, with the state of the world right now and how challenging everything is, I think to be able to do a show that has emotion to it —and joy. And I get a lot of joy from people on Twitter, where they feel like it’s a nice escape from their life for an hour. I think that’s the power of music and the power of positivity. The show is all about empathy and emotion, and connection. And I think that’s something that we can all benefit from right now.