Tim Sanford and Leslye Headland

Tim:  Leslye, why would a bright, capable young person such as yourself like theater? 

Leslye: (Laughs)  

How did you get enmeshed in this funny business? 

Oh my god, how can you not like theater?  I think I was just like most people who are young, and when they’re in high school they don’t really know what’s going on... and I fell in love with Stephen Sondheim.  I was obsessed with Stephen Sondheim.  I wasn’t really a musical theater nerd or a drama nerd but when I moved high schools, they were doing a production of Company and I really wanted to be in it.

Where was this? 

This was in Connecticut.  In Westport. 

Did they cast you? 

Yes,  I played Sarah.  It was a good production, too.  I loved it.  And that’s how I made all of my friends.

You said you weren’t a drama nerd, or---


You didn’t audition for plays or-- 

I did after that, because I thought, “I don’t have anything better to do.” Then the following year when I was a senior I directed Little Shop of Horrors on the Mainstage.

You must have impressed somebody.

I just thought that to impress people you have to look prepared, and you have to be prepared.  

Was that unusual to give a student that kind of opportunity? 

No, they would pick one or two seniors to direct a show.  And usually they direct in the black box, at my high school.  But every once in a while, if a senior pitches a good show, they’ll let them direct something on the Mainstage. 

Did you have any relationship with straight dramatic plays at this time in your life?

The boy that I liked, the boy that I got to make out with when I did Company, did The Bald Soprano as his senior project.  And I thought, “This is the greatest thing I’ve ever seen in my life.”  I loved that play!  I loved it.  Other kids were like, “That was weird.”  But I was laughing my head off. 

Well high school can be pretty absurd. 

Absolutely.  Then when I got to the Playwrights Horizons Theater School, I directed The Lesson when I was a third year.  Ionesco was actually one of the playwrights I knew about.   Also Eugene O’Neill.  I read a lot of Shakespeare when I was thirteen or fourteen.  If I didn’t understand it, I would buy the audio book and listen to it while I was riding my bike to school, and then read it again.   Hearing the performances helped me to understand the plays.

I need to introduce you to David Greenspan, because--

I am obsessed with David Greenspan.

Because when he and I went to see John Douglas Thompson’s Othello, he was comparing it to recordings of Olivier and Ralph Richardson that he used to listen to in high school.  

Greenspan is the only playwright that I’ve ever gone up to and introduced myself to unsolicited.  I saw him in an audience at New York Theater Workshop or somewhere.  And I went up to him and I said, “Hi, I just want you to know I think you’re a genius.” 

Were you interested in other things as a teenager besides theater?

I loved writing.  I did a lot of writing.

What were you writing?

I was writing these stories that were like veiled allegories, like C. S. Lewis.  I liked C.S. Lewis.  

Did you like him because he’s an allegorist or because he’s a Christian revisionist?

Because he’s a Christian revisionist.

Were you brought up religious?

Yes, very religious, so C.S. Lewis was like a great way of making peace with the rest of my family.  I saw him as kind of my bridge to being able to understand where I was coming from.  I loved Mere Christianity.  Incredible book.  And I loved The Great Divorce. 

When did you write your first play?

After college.

You didn’t write plays before then?

No.  Only directed in college. 


Yes.  At Playwrights Horizons, four years!  I loved it!

Was that always your plan? 

I thought I would go to Northwestern to study journalism.

Little did you know...

Little did I know you could become a playwright.  And I wasn’t a drama kid.

A serious person.

A serious person! My college counselor said, “You’re should go to NYU and audition for Tisch because you have this huge resume of all this theater stuff that you’ve done.” And I didn’t know about any of the studios except CAP 21, because I was in high school with a bunch of drama kids.  And I auditioned for this woman who said, “You’re not really a singer, are you?”  And I agreed. And she said, “Well do you wanna go here?”  And I said, “I want to go to Playwrights Horizons.”  I got in and then had a directing class with Fritz Ertl, and my design class with Michael Krass--

What made you say Playwrights Horizons?  

They had a list of their shows.  And I’d read The Heidi Chronicles and obviously listened to Sunday in the Park like a thousand times.  After my first directing and my first design classes I thought, “Oh, I want to do this for the rest of my life.”


I just loved it!  I loved directing class and I loved design class.  Loved.  It.   Class with Fritz Ertl blew my mind.  And with directing I thought, “I could probably talk my parents into this.” 

But your parents weren’t like super-judgmental...

No no no.  They are the sweetest people in the world, they’re just very religious.  That’s just that’s their vocabulary.  “Let’s pray about this.  Let’s talk to God about this."  They don’t just say, “Let’s follow a bunch of rules.” It’s actually a design for living with a spiritual basis.

What denomination were they? 

My dad’s Episcopalian and my mom’s Catholic.  I was raised Catholic.

So they didn’t mind you majoring in theater?

Well, my parents understand art, but they do not neccessarily understand the idea of giving your whole life to it and pursuing it as a career.  They’re like closet artists.  They got married very young and they had me very young and had four kids and they were going to make enough money to support those kids.  

Are you the oldest? 

Yes, maybe that’s where a lot of the directing came from, too, I think--just being left in charge of three kids all the time.  After a while you just put on West Side Story and you’re like, “Okay you go over here and you go over here and you go over here and you’re gonna be this guy who’s on the screen.”

There were four of you?  

Four altogether, including me. 

Have you heard that theory that all groups of four can be interpreted through a Beatles paradigm?

Oh my god!  I know what you’re talking about. 

You know what I’m talking about?  I think I read that in Fortress of Solitude, although he probably heard it from somewhere else.  

Oh for sure.  That was definitely true of us. 

Who were you?

They’d all say that I’m John.  And they’re probably right.  I would like to think that I’m George, but I’m not.  I’m probably John. 

What was the prize you got when you graduated?

The Robert Moss Prize for Directing. 

How’d you get that?

I directed Godot my senior year.

You seemed to like those theater of the absurd writers.

Love that play. 

What did you do when you graduated?

I got a job as an Assistant at Miramax while I was still at NYU.  I worked in the Archives Department.  The cool thing about it is that you get to go through a lot of the props and costumes that are used for the movies and this was during the Chicago, Gangs of New York filming. 

Were you an intern?

Yes, so I still had classes. So I would go be a student from eight until noon and then I’d work in the Archives department from twelve until six or seven.  Then I’d direct Godot in the evening until like one in the morning.  And it was just a great time in my life.  I just love being that busy.  Like even now, doing this play and finishing the mixing for the movie... I just love being that busy.  I love it love it love it. 

So when you graduated, did you get more responsibility?  

When I graduated I was lucky because one of the production executives needed an assistant.  I ended up working with a lot of great executives there, including Harvey Weinstein.  Working for Harvey was amazing!  When I was younger, Pulp Fiction had just come out, so I must have been about thirteen, and I kept seeing these photos for this movie in The Washington Post, and I wanted to see the movie even though I had no idea what it was about.  What I was interested in was who was it that was making me want to see this movie.  That’s what I thought was cool.  And it was also around the time Miramax had  Muriel’s Wedding and Strictly Ballroom and The Crying Game, then later Life is Beautiful and Shakespeare in Love--so from the time I was thirteen to eighteen, Miramax films were a huge part of my life.  And for somebody who wasn’t boy crazy and wasn’t really super-saturated with popular culture, Miramax films were things that my parents felt okay for me to see. 

Did you assume when you were studying theater that you would end up with a career in the movies?

Honestly, I kept thinking that only journalism was possible as a career choice.  But during all of this time I was directing theater.  I was directing Nocturne, I was directing Bash, I did these all-- 


In fucking basements!  I would literally put up all of my own money that I had just made after having worked overtime into a tiny production of Bash that no one was going to see.  I did a lot of Adam Rapp. I did a lot of Neil LaBute.  I did a Sarah Kane play. I did 4:48 Psychosis, by myself, basically.  For the three people that saw it.  I spent all of my free time doing that.  Any free time that I had, any free money that I had.  I would always blow it renting Under St. Marks’ space for a weekend, and pass out a bunch of postcards and... nobody came.  Finally I thought, “This isn’t working. I’ll just write a play.  I’ll write a play that’s got the right age group of people--” Because that was the other problem, tough to do O’Neill with a bunch of 23 year olds. Nobody wants to fucking see that.  We wanted to do Who’s Afraid of Virginia Woolf?I said, “We can’t do it. We can’t do it, none of us are the right age, this is terrible.”  And then I just said “Fuck it, I’ll just write Who’s Afraid of Virginia Woolf? but a 2004 hipster version.” And that’s Cinephilia. And Kirsten Dunst, who is in the movie verion of Bachelorette, came to see one of those productions. 


Kirsten just knew somebody who knew somebody!  It was literally her and two other people!  In a basement!  I kept thinking, “What is Kirsten Dunst doing here?” “Oh she knows so-and-so in the show.”  Talk about supporting theater.  Then later when we met for the movie, Bachelorette,  she said “I saw your play in a basement.”

Did you find out things about yourself as a writer by directing?

Oh, yeah.  That I was a bad writer.  (laughs).  I’d be like, “Oh my god, this section sucks.  This is fucking awful.”  It was a terrible play.  It got better.  It took me about four years to make it a decent 90-minute play.  Honestly. 

And during these years you were at Miramax? 


And when you worked as an assistant you said it became a 24-hr job.  Kind of like it is for your characters.


And did you have any choices to make... like your character? Did you have an epiphany or something?

No, I wish it had been that cool.  It was more like I had a really bad day.  And I thought, “I don’t know how to do anything.  The only thing I know how to do is write a play, which I taught myself over the last four years.”  And this was around the time when I came up with the idea for writing plays about the Seven Deadly Sins.  I was still working as an assistant, and I actually did what my parents had always suggested to do in times like this and I said, “You know if I’m not supposed to be a writer, then I don’t need to be a writer.”  I just sort of sent that out into the universe. I was like, “But the only thing I ask, Universe, is that if I’m not supposed to be a writer that you take away this feeling.”  You know, “That you take away this urge I have to be a writer.  But if it is my thing then I will live on a couch and I will be poor and I will do all of the things that I’m scared of doing,” you know what I mean.  And it wasn’t that the heavens opened up and Jehovah came down and said something, but a phrase did pop into my head, which was “Cinephilia’s part of a larger thing.”  That was it.  That’s all I got.  And it could have been me, it could have been somebody whispering in the corner, I don’t know.  I just kept getting that phrase, and thought, “Oh.”  And I had just started writing Bachelorette at the time and, and I kept thinking like, “Well, what could that be?  What does that mean, ‘a larger thing?’"  And because it had been sort of a spiritual experience, I thought, “Well maybe, maybe it has something to do with God."  And that was when it just came to me.  I just went, “Oh my God.  Seven Deadly Sins.” 

Were you still an assistant at this point?

I was about to leave, but I didn’t tell anyone. But once I had that feeling, I felt like I had the courage to go in and quit.  Because people don’t just quit Harvey Weinstein’s office.  He’s a big personality. 

Did he give you a hard time? 

No, he was terrific.  He was actually really nice to me about it.  He had read Cinephilia so when I said, “I’m gonna quit to go be a writer,”  he said, “You absolutely should do that, because you’re a good writer and you’re not that great of an assistant.”

So you said you were writing Bachelorette, before you had your a-ha moment, right?

Yes, and that’s one of the reasons I felt it was the right thing.  It wasn’t just, “Oh, we’re going to attach lust to this one after the fact and then move on to gluttony.” The reason I felt it was the right thing was that I had been having a big problem with Bachelorette because even though the characters sort of emerged fully formed, I had no idea what it was about.  And then I had this moment where I thought, “The bride’s overweight. That’s what it is.” And the entire play came within two months.

You were living in New York when you were working as an assistant.  Why’d you move to L.A.? 

I had some bad experiences with scam blackbox theaters.  People taking my money, claiming I broke a light at the end of the production so they could charge me more. I thought, “I’m gonna go to L.A.  It’s gotta be cheaper there to put up black box productions of my plays.”  And I was not going to sit around and wait for people to read my plays, either.  I wasn’t gonna do it. 

You moved to Los Angeles to do theater?!  You wild and crazy woman! 

I’m a trailblazer!  Blazing the trail.

What did you do to make money?

Oh my god.  I sold everything I owned basically, in a dramatic way.    And I just stayed with people.  I didn’t get an apartment.  Didn’t get a car.  Then I got a job.  I worked in a video store.  I worked in a record store.  My only rule with myself was that I was not gonna be an assistant again.  I would take any other job, pretty much, except the sex industry.  I thought, “I’m not gonna have sex for money and I’m not gonna be an assistant again.”  Even though at this point I’m 27 and I’m working jobs with eighteen-year-olds, taking the bus everywhere in Los Angeles...

You made enough money in these other jobs to self-produce again?   You formed a theater company, right?

IAMA Theatre Company in Los Angeles had already formed.  Amy Rosoff, Wes Whitehead, Katie Lowes, and Adam Shapiro were all people that I knew from Tisch.  I didn’t know them very well, but Amy and I had done a show together. 

Our Amy?

Our Amy [Rosoff, Jenny].  And I’d done Cinephilia with Amy.  She played Arden in Cinephelia about 30times.  Every time we did a production of it she was either in New York or LA already.  We remountedCinephilia with Amy and a couple of other people.  And it was a perfect match because as actors they were in the place that I had been like a couple of years earlier, “What play can we license that we can all be in?” I had two plays and we decided to just do them as quickly as possible--don’t charge too much; don’t spend too much.  Just make as much back as you spent.  And people kept coming. 

And did you direct Cinephilia? 

I directed Cinephilia and I directed Bachelorette.  I did not direct Assistance when we did it.  I was directing another show at the time.

One of yours?

Yes,  Surfer Girl.

You really were doing them quickly. 

Oh yeah! We did four plays in one year.

So how many of these plays were written after you moved to Los Angeles?

I finished Bachelorette, then I finished Assistance and Surfer Girl within the first year of living there. 

And Assistance was greed?   What was Surfer Girl?

Sloth.  Reverb is wrath and then Accidental Blonde is envy.  I haven’t finished pride yet. 

How did anyone know about Bachelorette?

The huge response to Bachelorette was completely unexpected. The second we opened in Los Angeles, people lost their minds over that play.  Young people.  But there we were, in a 50-seat theater off of Sunset Boulevard next to a Thai food restaurant.  

Did people recognize the moral impulse?  Did anyone know it was about one of the deadly sins?

No, that’s what’s so funny.  In L.A. we had audience after audience full of people who were 30 and younger, and all they thought was, “These are people I know.” 

Talk about Assistance.  How did that come to life?

I worked as an assistant for a lot of different people.  I struggled for a while about with writing it but then it all came together when I realized that the conceit is that it’s one of those stories where you never see the boss.

Plus as an allegory, isn’t he kind of like the devil?

I don’t know, is he the devil or is he God? 

Same thing, in a way.

Is it the same thing? 

And I think the point of your inspiration is that the play is really about “assistant-ness,” and it’s fine to exaggerate.  

Yes the play’s not about a particular person or a particular boss, but what we make them out to be, who we come to be, in how we deal with them. 

So you’re free to make it more and more outrageous because the point is not to write an exposé of some real guy but it’s really to dramatize the ruthlessness and the self-flagellation--


When you had the breakthrough, “Oh I can write about it, the boss won’t be in it.”  Did you know it was greed?

Right at that moment.  I was like, “Aaaaaand it’s greed.  Got it.”  Yep.

And how do you write?  This play has a particular structure--do you map it out in any way or is it instinctual for you? 

This is why I love theater.  When I write a screenplay, it’s so much about structure, outlining, index cards.  But writing a play...  there’s nothing better than starting a play, in my opinion.  Once I have that one thing, whatever it is, as soon as I’ve got it, I just sit down and within a short time I have a first draft.  The characters are just there, they just come out and they’re talking to each other.  Then, as soon as I possibly can, I get a bunch of actors in a room and I hear it out loud.  And that’s when I’m like, “WHOA!  There are so many ideas here; you’ve got to pick one of them.”  And then it’s a lot of re-writing.

The difference between the first draft of Assistance, which was finished in 2007-2008, and this one is absurdly different.  Nick and Nora are completely different.  I loved what you said Tim in the bulletin letterabout Nick and Nora and the significance of their names.  This is the kind of thing that I don’t even realize when I’m writing.  I always start with names.  And I thought “Nora” right away, because I knew she was going to leave at some point, like A Doll’s House.  Nick I couldn’t figure out for a while.  I think his name was something else like Luke or something and then I started doing their dialogue then I thought, “Oh nonono.  It’s Nick and Nora.  Obviously, that’s what it should be.”  But what you said about calling them a couple without them being a couple was something that I really didn’t know until I had workshopped it with you guys and had heard it with actors in a room again.  In the first production, the only hint of a relationship is that line, “The guy that I’m cheating on.”  And I thought whoever does a production can decide whether or not she’s talking about Nick. 

Leslye, isn’t this potential of their relationship sort of endemic to what you wrote? They make an immediate connection with each other.  Their minds seem to think alike.  And they both seem to possess deep feelings but they can’t afford to let their feelings go too much.  And that much is clear even before they became a couple.

Yes, that was always at the forefront of why I wanted to write the play. 

So we root for them to connect, even as we root for them to come through this job with their souls intact.  But their relationship is probably doomed as long as they work there.

And also I always thought it might be interesting to end the play with someone having left and someone being promoted.  I liked the idea that there were two ways to escape from that particular office. 

And what would be your response to the reductive question:  Are you Nora?

(Laughs)  I wish I was Nick...


I wish I was Nick.  I wish I had a nice little comeback for everything. 

You do, you just write it.

There’s always a character that I wish I could talk like.  Like in Reverb there’s June, this sort of sultry, Southern woman from Georgia who’s stuck in Silver Lake. It isn’t that she’s so smart, it’s just she’s always got a great comeback and she can handle the problem person in the play.  There’s usually the eloquent person in the play and there’s the problem person in the play.  There’s also the person who’s so sucked into the world of the sin that they don’t realize that it’s not working any more, like Regan inBachelorette.

What about that moment when Nora comes back?

For a while,  I wasn’t sure why she was coming back.  I wasn’t sure if she was coming back to see him or if she wanted something else. 

It’s developed so beautifully.  It’s like a Casablanca moment. 

I love that you said that!  I love the character Nick!  I love him!  And it’s kind of weird with my male characters sometimes.  I think with female characters, I just I assume I know what I will feel when I see them come to life.  I know what I’m gonna feel for Nora, I know what I’m gonna feel for Regan.  But when the male character Nick comes to life, or when Joe comes to life in Bachelorette, I think, “Oh my god, there he is.  He’s alive.  He’s talking.”  And Nick especially.  The guy is sort of like a sorcerer, but he’s like the Mickey Mouse sorcerer.  It’s like he thinks he’s making all these things happen and they’re not actually happening.  Like Nora’s arc goes from beginning, middle to end.  But Nick is like the indoctrinated character--the company man character--who really only realizes it in the last few seconds.  Like Regan only realizes in the last few seconds of Bachelorette what a devastating shitstorm she’s in. 

Talk about the interludes in Assistance.

A lot of the interludes came from knowing that I was going to be doing it in a blackbox theater, knowing I was gonna need time for costume changes, and knowing that I wanted time to feel like it was actually going by.  But also you’d only just met these characters and then they were gone.  I wanted to spend a little more time with them.  The interludes actually became the psychological through-line for the show.  Nick and Nora are the heart of the show--what happens to somebody’s soul and what happens to somebody’s heart.  The interludes are what happens to somebody’s brain.  In a way, I think each one is about how that assistant becomes Daniel in some way.  It’s the only time you ever get to see Daniel, really, is in the interludes.  Vince’s monologue is how Daniel does business.  Heather’s monologue is how Daniel lets out a frustration on someone he knows is never going to leave.  Heather lashes out at her Mom because her mom can’t leave.  She and her mom are connected.  Justin represents the idea of that lust for that power and for that greatness, that some people just don’t have.  I don’t think everybody’s created equal.  The superstar boss or mogul has that job for a reason. And for someone like Justin, I think to be near that and be around that is probably the best thing that will ever happen to him.  And I think that sometimes people have to admit that to themselves. 

And Jenny.

Yes, then obviously there’s Jenny.   You know her dance is funny.  When I wrote it I was so excited by it.  But I wasn’t sure exactly what it would be physically.  And my director in L.A. asked me about it.  She was really struggling with it and not quite sure what it meant and what it was supposed to be.  And she actually said the words, I’m not even joking, she said, “If this was being done at Playwrights Horizons, what would it look like?”  And I didn’t know! 

Did you learn about it as you watched it?  Did it start to make more sense to you?  Or is it still kind of a mysterious thing?

There’s a deep level right here in my gut where I believe it makes sense.  As soon as I typed “She dances forever.  She never stops.  Her dance destroys the space,”  I thought, “Oh, yeah.  This is what happens.  This play ends with a huge, epic tap dance of Singing in the Rain proportions.” Sometimes it’s hard to know how to end things, so it felt good to have an ending that feels like an ending.

Trip [Cullman, Director] sometimes references Singing in the Rain when he talks about the ending. Flashdance too.  He and Jeffry Denman [Choreographer] have such a clear vision of what it should be.  Has it started to make logical sense for you?

I think the reason it’s relevant is because nothing actually happens in this play.  Physically nothing happens to the space.  Nothing happens to Daniel, he’s not threatened in any way.  When I was writing Jenny’s monologue I was trying to think of what would actually threaten Daniel, like what would “destroy Daniel.”  What would destroy the idea of him?  And I thought skill would actually do that.  Nobody’s shown any skill throughout the play.  Like Nora says, “We’ve just been perfecting the art of dodging responsibility.”   And I thought, “What skill should she have?” And then I thought, we’re on a stage and stages are meant to be tap danced on.  So there’s a performative aspect to it that felt right.  

One of the things we talked about early on is why it’s Jenny.  Why does Jenny get the final moment?  

Right.  “Why isn’t it Nora?  Why does Jenny get sort of this triumphant moment?”  And I think it’s because as much as she may want it to be, Nora’s not going to be Daniel.  Somebody else will be.  I think it would be backwards to say that Nora has that triumph.  I think the Jennies of the world have that triumph.  A lot of times, especially in films, people seem to be rewarded for the wrong behavior;  meaning if someone’s sort of good and nice and sweet and moral they get all the stuff.  And in reality, I don’t know if that happens very often. 

That makes sense to me.  And I also think on a certain meta-theatrical level, Nora has escaped.  I think the dance transforms the story, in a way.  It’s like an artist’s revenge, in a way.  There’s something rigorous and aggressive about a tap dance.  But there’s also something pure about it as well.  It is sort of pure artistic expression.  At least, that’s what I’ve begun to take away from it. 

One more question.  What are they making? 

Oh yeah NOTHING!  They’re not actually making anything.  

I always inferred in Vince’s monologue that he could be talking about an actor.  

Sure, I can see that, but all he says is, “He could do it.”  And I love that phrase.  “He could do it. He could totally do it!”  Do what?  For this play, I think it’s important that it’s not movies actually, because I love movies.  I think that if it were about making movies, it would actually be a much more flattering play than this one. But I think it’s important for everybody, that no matter what job you have, there has to be some moment when you stop and think, “I’m not actually doing anything.” And you have to push that back down inside of you in order to keep going.  You have to believe that there is something larger going on in order to keep pushing forward.  If you don’t have that connection to something larger than yourself, then you have to push that down into a tiny little box and continue to work.  It will make you crazy to think about whether or not what you’re doing is important. 

Tolstoy had this great religious conversion at the end of his life.  And there’s a quote*, this point where he realized--not in an existential, cool way--that his life really meant nothing.  And this is from the guy who wrote Anna Karenina.  He decided that ultimately, his existence, without any connection to something bigger, was nothing.  Even his art.

*The question brought me to the edge of the abyss...  Is there any meaning in my life that will not be destroyed by my inevitably approaching death?

My deeds will be forgotten sooner than later and I myself will be no more.

Why then do anything?  I therefore could not attach a rational meaning to a single act to my entire life.  The only thing that amazed me was how I had failed to realize this at the very beginning... 

It is possible to live only so long as life intoxicated us; once we are sober we cannot help seeing that it is all a delusion.

-- Tolstoy, from A Collection of Religious Writings