Showtime’s Work in Progress has gallows humor, smart writing, and Lilly Wachowski

“This show is queer as fuck. Queer and trans as fuck.” What’s not to love?

If I told you that Showtime’s new series Work in Progress marked the first foray into half-hour television for Lilly Wachowski, one of the visionary directors behind The Matrix trilogy, and Speed Racer, and Bound, and — honestly, I could list everything she’s ever made — you might picture something drastically different from what you will see when you tune in. But you should definitely tune in! It’s very, very good.

Instead of a cosmic tale that transcends time and space, Work in Progress is the story of a middle-aged queer woman, one who’s gender non-conforming, overweight, and struggling with suicidal ideation while living in Chicago in the late 2010s. If Wachowski’s other work tries to find the specific in the universal, Work in Progress finds the universal — our sadness and loneliness and fears — in the hyper-specific.

But though Wachowski is working as an executive producer, writer, and showrunner on the series, its hyper-specificity comes from its star, co-creator, writer, and co-showrunner Abby McEnany, a comedian and performer from Chicago who has grounded Work in Progress in her very real experiences and life. The opening three minutes of the first episode — essentially a very dark comedic sketch — are at once some of the most heartbreaking and hilarious I’ve seen on television this year.

And everything that follows is thoughtful about a wide range of topics, from gender identity to the intersection of queer identities and mental illness to Julia Sweeney, the Saturday Night Live performer who invented the character of Pat, whose ambiguous gender was the bane of existence for gender non-conforming folks like McEnany. Sweeney even appears in the series as herself.

Work in Progress is smart about all of this stuff and more. And when I found out it started its life as an independently filmed pilot, I wanted to know so much more about how it came to be, how it ended up on a major network like Showtime, and how Lilly Wachowski got involved as a producer. So I jumped at the opportunity to talk with McEnany; her co-creator, director, and co-showrunner Tim Mason; and Wachowski herself (after hyperventilating a little) about the process of making Work in Progress.

A transcript of our conversation — lightly edited for length and clarity — follows.

Amy Sussman/Getty Images

Emily VanDerWerff

So you produced this pilot independently, then Showtime acquired it as a series. That’s a pretty rare way to get a TV show on the air. How did you decide to pursue that strategy?

Abby McEnany

There was no other way for us to do it. So it was just like, “Well, you do it yourself.” I don’t know how to answer that! We just knew nobody would pick it up, or how [we would find someone who would]. We didn’t know anybody. How would we get a meeting? So it just came down to: “Well, we’ll just do it ourselves.”

Tim Mason

We actually were like, “What if we shot this and then we put it online in chunks, and it’d be a web series?” And then we put it into chunks and it really didn’t work. It worked as a full pilot. I had been taking general meetings after this short film [a different project], and I told Abby, “I’m so sick of meetings that don’t lead to anything. We didn’t get into this to have meetings. We got into it to make stuff.” So we looked at the budget and were like, “What the hell, let’s go do it.”

Abby McEnany

We had to come up with $30,000, and we did.

Emily VanDerWerff

As someone who enjoys meetings —

Abby McEnany

[imitating Emily] “And at that moment, I had nothing in common with the Work in Progress crew. They hate meetings?! That’s a bunch of bullshit!”

[all laugh]

Emily VanDerWerff

I’m sorry! I do! When you were making the pilot, though, did you think there might be a platform for it? Or did you just want to make it the best it could be?

Abby McEnany

The goal was always to make a TV show. Create this thing. Make it as as great as we can on our budget and [with] our limited time. Then the goal is like, “Let’s try to sell this thing, and how are we going to do that?” So the goal was always to create an episodic TV show.

Tim Mason

What’s amazing is the favors that we called in for some people, like my editor, some of the cast. You know, like the cast came in, and it was, like, on an ultra-low-budget SAG agreement. So they got paid $125.

Abby McEnany

Julia Sweeney got $125 for the pilot.

Tim Mason

People did it basically as a favor. Now, because Showtime’s putting it straight on air, those people became cast members. We were all in together. And so my editor is now coming on as the editor for half of [the series]. The [director of photography]. Everyone. Everyone who gave us favors, we tried to keep in the family.

Emily VanDerWerff

Lilly, you have a unique perspective on this, having joined the project a little later. [Wachowski joined the pilot on the basis of its first scene, a three-minute act with Abby in therapy.] You must get handed a lot of stuff. What was it about this?

Lilly Wachowski

As a viewer and supporter, I was in when I saw the first three minutes a year and a half ago.

Tim Mason

We had filmed those first three minutes a year before.

Lilly Wachowski

But even before that, I was into Abby, after seeing her one-woman shows. I knew what a brilliant and unique storyteller she was. You don’t get opportunities to work with people like that a lot. And so I was like, “I’ll do whatever I can to help you guys get the show into whatever form it’s going to take, because I want to see the show.” It’s amazingly funny and beautiful and touching, and all the things that you want a show to be.

Emily VanDerWerff

How have you found the process of writing for half-hour television?

Lilly Wachowski

There was this investigation that took place to figure out what the thing was. Make the thing, and then figure out what the thing is after. Once they made the pilot, it was just, like, “Well, what’s going to happen?” The pilot has been so perfectly set up with this idea of the person who has suicidal ideations and has given themselves 180 days to live. It’s like you’ve built in this ticking time bomb in the plot of the show.

There was no question in my mind that you had this very A to B structure, which was like, “Okay, last episode, no [time] left, what happens?” If you’re riding a roller coaster, what are the ups and downs? We’re trying to find it. Tim is constantly reminding us all the time, “Whoa guys, this is a comedy, don’t forget. It’s supposed to be funny.” No, it’s dark. Heading towards the darkness.

Abby McEnany

That’s kind of my go-to.

Lilly Wachowski

So once you have this whole picture, then you go, where do you make the cuts? And it’s just like you’re telling these acts. So in our case it’s like an eight-act thing. The first act [the pilot] is done, and then you can make little compartments [for the other acts].

Showtime

Emily VanDerWerff

A lot of Work in Progress takes place in the intersection between queer identities and people who have mental illness. What did you find interesting about that intersection? What stories lie there?

Abby McEnany

I guess I’ve always wanted to just tell my truth and be very open about it. I have no shame about telling people that I have mental illness. So I didn’t even think [about] it that way. I just think it was, like, tell this story. I really am just constantly trying to figure this shit out. What am I doing? I’m trying to be open with that stuff.

In the last few years, to me, just the idea of gender and sexual fluidity has opened up a lot of freedom. To me, my relationship with Chris [a character on the show] is based on a real relationship I had with a young trans man I met. I was in DC for a month, years ago, and I met this lovely man. We dated and then we did long-distance. And this woman who I’ve known in the community, was like, “You’re dating a trans man? Well, I guess you’re not a lesbian anymore.” I’m like, “Who fucking cares? Do you have a list?” In my mind, she has this big whiteboard in her home.

So I don’t even know. When all the crew heads [met for the first time], Lilly introduced us, and everybody got up and said what they were doing and their pronouns. I was like, “She, her, hers. Could change tomorrow.” There’s so much more openness now. So you’ve just got to tell the truth, barf it all out, figure shit out.

Emily VanDerWerff

You want to honor this ticking clock around the character’s suicidal ideation, but Work in Progress is a TV show that might run for many years, so you don’t want to treat the topic callously. How do you tell that story responsibly?

Abby McEnany

That is something that’s very concerning. It’s a comedy, but we people having suicidal thoughts — that’s not funny. But it’s, like, humor [is] the reason that I’m still alive. Sometimes it’s very dark, but that’s a mechanism for me and several people to survive. But we’ve checked in a bunch to make sure, are we honoring that darkness? We don’t want it to be glib. This is real shit that people are dealing with. I hope we do it right.

Lilly Wachowski

In this show, it’s coming from a real place. To be able to talk about suicidal ideation and to do it with humor is important. We do enough of not talking about suicidal ideation. So we do it with humor as an entry point for people to enter into this discussion and get seriously involved in this kind of dialogue. When we talk about the character, for me, it super resonates as somebody who’s battled depression and my gender dysphoria. Knowing that Abby has gone through her own depression, I think we’re definitely being sensitive about it. But it’s more like a welcome mat to start talking about these topics.

Abby McEnany

The goal is, we’re not making fun of it. A lot of comedies I love, there’s one thing like, “God. Really? It’s fun to make fun of fat women? Whatever.” Everything’s great about the show except for that one thing. So hopefully we’re honoring the experience and not making fun of the people, or the fact that people live through this stuff. That’s like opening conversation. Because it’s not funny that people are so desperate that they want [to] end their life. That’s not hilarious. It is devastating and tragic and real.

But the way the three of us have created Work in Progress is to talk about it in a way where it’s all about losing that shame of mental illness, that stigma. People don’t talk about it.

Emily VanDerWerff

I know how these things get sold. This show will be sold as, “From Lilly Wachowski, director of The Matrix, etc.” People are going to come into it expecting one thing and get something very, very different. So, what’s the intersection of the grand cosmic scale that Lilly’s other projects have been on and this tiny little project?

Lilly Wachowski

I think the intersection is that this show is queer as fuck. Queer and trans as fuck. I think all the trans people that come up to me and say, “Oh my God, The Matrix! It unlocked so many things for me. Thank you so much.” All those people will watch this show. They’re going to watch the show and they’re going to really like it. Because it’s sweet and it shows trans people and queer people in a very normalizing and loving way.

Tim Mason

As we were working, I was like, “I’m gonna watch Cloud Atlas.” With the budget that I’ve been working on for this show, there’s nothing like sitting down and watching Cloud Atlas and being like, “Oh my God, we are coming from such different filmmaking backgrounds.”

At the crew head meeting, we were talking about cross-shooting [shooting scenes between two characters by alternating focus on those characters, with the camera always focused on the person furthest from it], and I said I had had really good luck with it on this crap mac-and-cheese commercial. Lilly was like, “Oh well, we did it on Cloud Atlas.” [all laugh]

Abby McEnany

[imitating Tim] “Well, on my Cloud Atlas, crap macaroni-and-cheese commercial…”

Tim Mason

The intersection I see is the respect for the emotional truth that the characters have that exists in those giant, beautiful films of Lilly’s, and then in this tiny thing. There’s a lot of similarities, that it has to do with how you respect your characters and how you treat your characters.

Emily VanDerWerff

Well, I will be sure to headline this interview, “Work in Progress: It’s just like Cloud Atlas.”

Work in Progress (a TV series that is exactly like the 2012 Wachowski magnum opus Cloud Atlas) debuted Sunday, December 8 on Showtime. New episodes air Sundays at 10 pm.