Talking to Hilary Winston About Writing for ‘Community’ and ‘Happy Endings’ and Adapting ‘Bad Teacher’ to TV

Comedy writer and producer Hilary Winston has been building quite the impressive resume these last few years, jumping from critically-acclaimed show to critically-acclaimed show. After spending four years on staff for My Name Is Earl’s entire original run, she did two seasons at Community and then two seasons at Happy Endings. Now, after years of writing on other people’s shows, Winston has one of her own with Bad Teacher, a half-hour sitcom based on the film of the same name that premiered on CBS last week. Winston adapted the Bad Teacher to TV, serving as the show’s creator and showrunner.

Starring Ari Graynor, Sara Gilbert, Ryan Hansen, Sara Rodler, Kristin Davis, and David Alan Grier, Bad Teacher has been picked up by CBS for 13 episodes, which will be airing on Thursday nights over the next several weeks.

I recently caught up with Hilary Winston to discuss her beginnings in television, what she learned from writing for My Name Is Earl and Community, and adapting Bad Teacher.

How did this project come about, turning Bad Teacher from a movie into a TV show?

My friends Lee Eisenberg and Gene Stupnitsky wrote the movie, and I really thought that it was such a funny script. It was a hilarious script and such a great concept. And they told me, “We’re thinking about turning it into a TV show.” And every time I went to lunch with Lee, I said, “I think you should do this, and don’t do this, and I would not do this,” and then finally, after tons of those kinds of lunches, he said, “Would you consider writing it?” and I said, “Yeah, you know, actually I would.” But I said, “I think I’d want to dump pretty much all the backstories and stuff from the movie and just start over with just the concept.” Lee and Gene were really open to that. So for me, that put me on board. I love the concept, I love the archetypes from the movie, but I really wanted to start fresh with a clean slate for this new Bad Teacher.

What type of challenges do you face when you’re taking an established product and then adapting it for TV? I know you said you sort of wanted to make it your own a little bit, but how can you still stay true enough to the original so it doesn’t put off fans of the movie?

That’s really the challenge, especially with the movie where some people say, “I love the movie,” and some people might say, “I hate the movie.” You really have a lot of challenges making it with existing material. So to me, I of course wanted to please people who really loved the core idea of the movie. In order to do that on network TV, you really had to ground the world. Because what works in a rated R movie is very different from what works on a sitcom. At the time we were making it, we didn’t know — we could have been on at 8 o’clock — how to make it work. So it was really about grounding the world so that in our show, the bad teacher’s name is Meredith, so Meredith’s connection with the students and the way she dealt with her interactions could kind of be what was edgy. Her interactions with her other teachers could be edgy because the world felt real. If we started in kind of a bigger world, like the movie, there was really nowhere to go in the network TV world.

As far as making the show edgy, what kind of stipulations were put upon you by, for instance, CBS? When you compare the movie, which was pretty raw and you have to go to primetime television, what boundaries did you work within?

It was like a battle. You know, going back and forth. You want to have a lead character who is still likable and when you have a lead character who’s bad — in any other show, the bad teacher would kind of be part of the ensemble, not the lead — so you have this character who’s the lead who can’t get away with as much because she really needs to feel like you’re watching the show through her experience and then you want what she wants and all that and it’s hard if her motives are really suspect. So, I think that, for us, it was always kind of pushing back on the network, we need to be able to push her far enough that the show still has edge but then we can’t push her so far that you’re not interested in this character anymore. So that was always the battle and I think that the network and studio and, at first, the writers’ room kind of had different ideas of where that line was. We all probably have different favorite episodes but, to me, what I think is fun is that we were still able to do a lot of that edgy stuff that we wanted to do; we just kind of had to be a little smarter about it.

What was your involvement with casting the show?

I was totally involved in every step of the way on casting. David Alan Grier, I think, is the first person we cast. I had worked with him on Happy Endings, and I felt like he was this American treasure, you know? He’s just amazing. With a lot of people like Sara Gilbert, we got coffee with her, we talked, she really connected with the character and everybody came to it in such a special way and it just started building. I mean, how did I get so lucky to have a cast like this that all comes from such different walks of comedy life? Kristin Davis, all those years on Sex and the City and what a different type of comedy that is from In Living Color, or from Roseanne, or any of the movies that Ari [Graynor] does; she’s like a scene stealer in everything. Then you look at Ryan Hansen and what he did in Party Down and Burning Love, and it’s just so interesting to see how all of them are different and then work so well together.

How has working on Happy Endings, Community, and My Name is Earl prepared you for Bad Teacher?

Everything you work on, even the stuff that doesn’t get mentioned — my first job was on a Nickelodeon show — it really prepares you for how you want to do things, the stories you want to tell. Every story you ever break in your career, which is like hundreds and hundreds of stories, prepares you to tell the next story. I got to work with Greg Garcia, who is one of the most amazing story-breakers I’ve ever worked with, on My Name is Earl. I got to work with Dan Harmon, who pounds out stories in such a totally different way. We all kind of know the story embryo that he talks about, Joseph Campbell. I mean, before you even start breaking a story, Dan can probably talk for hours about the idea. So, it’s just different ways of approaching a story, and it was so great to have those ways in my head. There were some days where I’d go in the writers’ room, and I’d want to break a story like Greg Garcia does, with precision. Then, some days, I would come in and I would put a story circle up, and I would say, “Hey, this is Dan Harmon’s story circle. This is how we did it at Community, let’s throw it up on a circle and use the storyboard.” I just felt I had a full toolbox by the time I had my chance to run a show.

A few years ago, your book, My Boyfriend Wrote a Book About Me, was picked up by Paramount, and you’re currently working on the script. Can you tell us anything about that project?

I did write it as a movie script, but I don’t know what’s happening. It’s so funny coming from TV, which moves so fast — we started the show a year and a half ago and now we’ve shot 13 episodes — and then turning to the movie world, which is so slow, so beautifully slow. So, I can still be talking about the movie in 10 years.

How did you get your start as a writer?

The TV Academy that does the Emmys has an internship program, and they let you apply after you get out of college for a year. I was interning and working as a research assistant at NPR, and I was just kind of like trying to find a legitimate way to write that my parents will respect, and I kind of realized I’m sick of finding real stories; I would just much rather be making up stories. I applied to this internship program, and you had to write a spec script, which I hadn’t written before. I got it, and they placed me on the hit comedy Star Trek: Voyager. So my first job was as a writers’ assistant on Star Trek: Voyager, with amazing people like Brian Fuller — who I think was a staff writer or story editor when I was there; he did Pushing Daisies, which I adore — and Rob Doherty, who was a freelance writer at the time and created Elementary. I’m so excited that Bad Teacher is on at 9:30 and Elementary is on at 10. It’s just very exciting because we all started off at this internship program. It was a really cool, random way in.

Who are the writers you most look up to?

I think that the show that I probably watched the absolute most growing up was M*A*S*H. I think that Larry Gelbart — just that kind of style, being able to talk about something real and still be laughing while you’re doing it — was really inspirational. Also, The Muppets. I always loved The Muppets. The Muppet Show was so underrated because they literally could be singing about The Vietnam War and, you know, they’re puppets and it was amazing. So I think those kind of things that I watched as a kid really influenced what I wanted to do.

Thinking about all the projects you have going on, you really have an impressive trajectory going. But what is a dream project that you feel would be your crowning achievement as a writer or showrunner? 

I think that in the world we’re in now with such amazing stuff being done on cable with so much freedom, I think that we all believe that we’re kind of earning our shot at doing an amazing cable series where we don’t get any notes and we can make it exactly what we want it to be. I’m a huge Game of Thrones fan, and you look at a show like that, and it just makes you want to be a better writer. So I have to say that I would love to have my shot at a notes-less, amazing passion project on a cable hour.

But I have to say, although that’s something I’d like to do in the future, I’m so happy doing network TV. I grew up on it. I did homework in front of the TV every night — and my parents were still good parents — with Cheers and M*A*S*H and Roseanne and everything. I really feel like there’s something special about network TV. It’s not in a good place right now, but I think that it can come back. I believe that there is something valuable in it, and it’s why I don’t write movies. I mean, other than a movie adaptation of a book. But because there’s something special about letting these characters into your home every week and how close you get to them and what you can do with those kinds of characters that can be on TV for seven years. It’s so cool, and there’s really nothing else like it.

What other projects do you have in the works that we should be on the lookout for?

You know, this has been all-encompassing, but I’ve been writing a column for Playboy, which has been really fun, and I definitely think there is a possible series in there and in some of those ideas. So it’s been a fun, experimental platform for writing my ideas.

New episodes of Bad Teacher air Thursday nights at 9:30 on CBS 

Photo credit: Jay L. Clendenin/Los Angeles Times

Isaac Kozell is a writer and standup comic. 

Talking to Hilary Winston About Writing for […]