Work in Progress: Gallows humor, smart writing, and Lilly Wachowski – Vox.com

If I told you that Showtimes 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 shes ever made you might picture something drastically different from what you will see when you tune in. But you should definitely tune in! Its 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 whos gender non-conforming, overweight, and struggling with suicidal ideation while living in Chicago in the late 2010s. If Wachowskis 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 Ive 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.

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

There was no other way for us to do it. So it was just like, Well, you do it yourself. I dont know how to answer that! We just knew nobody would pick it up, or how [we would find someone who would]. We didnt know anybody. How would we get a meeting? So it just came down to: Well, well just do it ourselves.

We actually were like, What if we shot this and then we put it online in chunks, and itd be a web series? And then we put it into chunks and it really didnt work. It worked as a full pilot. I had been taking general meetings after this short film [a different project], and I told Abby, Im so sick of meetings that dont lead to anything. We didnt 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, lets go do it.

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

As someone who enjoys meetings

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

[all laugh]

Im 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?

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, Lets try to sell this thing, and how are we going to do that? So the goal was always to create an episodic TV show.

Whats 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.

Julia Sweeney got $125 for the pilot.

People did it basically as a favor. Now, because Showtimes 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.

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?

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

We had filmed those first three minutes a year before.

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 dont get opportunities to work with people like that a lot. And so I was like, Ill do whatever I can to help you guys get the show into whatever form its going to take, because I want to see the show. Its amazingly funny and beautiful and touching, and all the things that you want a show to be.

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

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, whats 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. Its like youve 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 youre riding a roller coaster, what are the ups and downs? Were trying to find it. Tim is constantly reminding us all the time, Whoa guys, this is a comedy, dont forget. Its supposed to be funny. No, its dark. Heading towards the darkness.

Thats kind of my go-to.

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

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?

I guess Ive 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 didnt 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? Im 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 Ive known in the community, was like, Youre dating a trans man? Well, I guess youre not a lesbian anymore. Im like, Who fucking cares? Do you have a list? In my mind, she has this big whiteboard in her home.

So I dont 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. Theres so much more openness now. So youve just got to tell the truth, barf it all out, figure shit out.

You want to honor this ticking clock around the characters suicidal ideation, but Work in Progress is a TV show that might run for many years, so you dont want to treat the topic callously. How do you tell that story responsibly?

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

In this show, its 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 whos battled depression and my gender dysphoria. Knowing that Abby has gone through her own depression, I think were definitely being sensitive about it. But its more like a welcome mat to start talking about these topics.

The goal is, were not making fun of it. A lot of comedies I love, theres one thing like, God. Really? Its fun to make fun of fat women? Whatever. Everythings great about the show except for that one thing. So hopefully were honoring the experience and not making fun of the people, or the fact that people live through this stuff. Thats like opening conversation. Because its not funny that people are so desperate that they want [to] end their life. Thats 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 its all about losing that shame of mental illness, that stigma. People dont talk about it.

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, whats the intersection of the grand cosmic scale that Lillys other projects have been on and this tiny little project?

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. Theyre going to watch the show and theyre going to really like it. Because its sweet and it shows trans people and queer people in a very normalizing and loving way.

As we were working, I was like, Im gonna watch Cloud Atlas. With the budget that Ive been working on for this show, theres 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]

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

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

Well, I will be sure to headline this interview, Work in Progress: Its 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 11 pm.

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Work in Progress: Gallows humor, smart writing, and Lilly Wachowski - Vox.com