This is a transcript of the Final Draft Insider View, a podcast that takes you inside the screenwriting industry to talk with screenwriters, television writers, executives, and industry influencers. To listen to the podcast click here. To listen to other podcasts visit podcasts.finaldraft.com.

Pete D’Alessandro: This is the Final Draft Insider View, a podcast that takes you inside the screenwriting industry to talk with screenwriters, television writers, executives, and industry influencers. Hello, I'm Pete D’Alessandro. Welcome to another edition of Insider View. Today our guest is Phillip Iscove. He is the creator of and writer behind Sleepy Hollow, the TV show. Phillip, thank you so much for joining us.

Phillip Iscove: My pleasure.

Pete D’Alessandro: So I wanted to talk a little bit about how you got into the industry and what you've kind of done up till now, because I know this is the first thing you've sold, and it was a big deal, and I guess that only happens to everybody once.

Phillip Iscove: [Laughs] It does only happen once. You know, honestly, the truth is that all of this sort of happened pretty crazily for me just in the sense that I worked at…well, first and foremost, I went to film and television school back in Toronto, and then I sort of kind of wallowed in…well, wallow’s probably the wrong word, but post-graduate malaise I guess is probably the best way to put it, and my parents were sort of watching, wondering, “What is he doing?” My father at the time had been sort of working back and forth between LA and Toronto and became friends with an entertainment lawyer who was able to make the introduction to UTA, where I worked in their mailroom and worked as an assistant for almost eight years.

They sponsored my visa and they allowed obviously for me to stay in the country and they supported me and continue to be a tremendous company with support for me. I worked for a TV lit agent who is now my agent. I worked for him for over five years and wrote in my spare time.

I wrote five pilots and two features while working for him and just sort of went in every weekend and just kept writing and sort of used his relationships, if you will, and kind of built off of his relationships, and before I knew it I was sort of…you know, I had a handful of executives that were reading my stuff and supporting me in trying to sort of find work for me.

And then ultimately it became clear to myself and to my agent that I needed to get out of UTA, obviously, and my visa was set to expire and I went to him and said, “I'm going to get kicked out of the country in September if I don’t sell something,” and I sold Sleepy Hollow. It was one of those things where, I mean obviously I'm sort of giving the short version but, you know, we pitched it to a handful of places and Kurtzman/Orci – K.O. was the last place and Alex and Bob flipped for it, and the rest is history.

Pete D’Alessandro: Wow. I mean, that’s amazing. So did you have any kind of relationship with them before that?

Phillip Iscove: I did not have a relationship with Bob and Alex, no. I had a relationship with one of their executives who took the time to hear the pitch, and she was like, “I think Alex and Bob would be really into this.” I was like, “Cool.”

And a couple of days later I was sitting in front of them and it was pretty clear very early on that this was a project that made sense for them and, you know, it was one of those things where you're sort of sitting in that room and five minutes in they're sort of spitballing ideas and you're like, “My God, they get this. They know what to do with this,” and it was sort of a no-brainer.

Pete D’Alessandro: So how was the rest of that ladder of pitching up from there once you had them on board?

Phillip Iscove: Well, I mean, we attached Len quite quickly after that. Bob and Alex had worked with Len on Hawaii Five-0 and Len was game and phenomenal, just a visionary in terms of how he saw the show. He just immediately got it. He immediately understood sort of the high-wire act that is the show. It's a pretty rich stew and you’ve got to make sure that you don’t tip into cartoonish or just sort of the outlandish, if you will. You have to find that weird balance, and I think that Len understood that right away. And Bob and Alex and myself, so the four of us, kind of started breaking a very loose sort of pilot story and kind of started digging in and, you know, it goes without saying that when you're working with Bob and Alex and Len, a lot of doors open very quickly.

So it was one of those situations where we didn't have to…you pitch to the right people at the right times and it just sort of…it all happened…I mean, it was truly insane, and I mean that with all due respect to everybody. You know, I'd never been a part of anything like this, so for me it was just like I was just holding on for dear life. I'm just making sure that I was as much of an asset to the show as was humanly possible and allowed, more than anything, allowed Bob and Alex and Len to flourish, you know?

Pete D’Alessandro: Sure, sure, just kind of stay out of the way that the guys who have been down this road…

Phillip Iscove: A little bit, yeah.

Pete D’Alessandro: So what else had you written before this on your own? I mean, how far had any of that gotten for you?

Phillip Iscove: I had a couple of pilots that, or one pilot in particular that got a little bit of traction and enough traction that it got me noticed. I wrote a pilot that was sort of about a—I cannot even explain it—a 17-year-old Japanese Jewish girl who’s sent away to an art school rehab in Minnesota, which is sort of a Felicity/Through the Looking Glass, you know?

It was really kind of this coming-of-age sort of story of a girl kind of finding her artistic voice. And I wrote that and it got a little bit of traction at places that you would assume it would. It was a young story and a young sort of cast, so the major networks, it's not really in their wheelhouse. So it was a couple of places that showed interest in it. And then I wrote some other pilots, and it was honestly one of those things where what I was hoping for, quite honestly, was to start at the bottom and to be a staff writer and to work my way up and to learn the ropes, quite frankly, sort of slowly.

That was always sort of…that was the pie in the sky, quite frankly. Nothing like this was ever even on my radar.

Pete D’Alessandro: Of course, of course. I mean, that’s a wildly different way to traverse the business.

Phillip Iscove: [Laughs] Yes, absolutely, absolutely.

Pete D’Alessandro: That’s fantastic.

Phillip Iscove: So yeah, I mean, it was really just one of those situations where I had learned a tremendous amount in film and television school and the almost eight years at UTA had taught me a tremendous amount about the business of television and the business of this industry. And so for me it was just sort of now I was given this unbelievable hands-on keys to the kingdom, if you will, so it was really just a matter of making sure that I used what knowledge and experience and talent I had and apply it to the show.

Pete D’Alessandro: Wow. Okay. So I was curious about the specifics of what kind of…I mean, if you were at UTA for that many years, I imagine you've got insight that a lot of people do not get.

Phillip Iscove: It's true. [Laughs]

Pete D’Alessandro: What kind of stuff did you wind up taking away from that that winds up applying to what you're doing now?

Phillip Iscove: I think it was just an understanding of why something sells. I think there's this unfortunate misnomer that something has to be inherently bad for it to sell. [Laughs] Do you know what I mean? And I mean that in the best possible way, but I do think that as writers and as just creative people tend to look down their nose a little bit at the business of what we… because there's a lot of sort of, I don't want to say naiveté, it's the wrong word, but just people that immediately think a note is bad or immediately think that an agent doesn’t know what they're talking about. And they might not be wrong, a lot of the time they're right, but they're not always wrong and I think that what I took away from working at UTA was just trying to sort of understand why something sells and how to make it good and to make it sell. How do you find a way to not get lost in the sort of minutiae of sort of how do you make something lucrative and try to make sure that you sort of understand kind of like the framework of why a network wants to buy something or how do you get something marketable? How do you get something that can pop off the screen? And I guess more than anything it was just sort of trying to figure out the pulse. You can chase the zeitgeist as much as you want I guess… but at the heart of it, what is it really all about? I got incredibly lucky with my situation. I looked at the landscape of television and I saw that there was a whole bunch of genre stuff going on and I was like, “Okay, well, there's an opportunity here. There are all these sort of fairy tales and there are all these sort of public domain titles and blah, blah, blah.” And then it was like sitting in front of my computer and looking at public domain titles and figuring out how I can make that my own.

And Sleepy Hollow, Washington Irving pops up on public domain, you see Rip Van Winkle, you see Sleepy Hollow, and you think, “I can just put him to sleep, can’t I, and he just wakes up in 2015?”

Pete D’Alessandro: [Laughs] That’s a much more affordable way to do that sort of piece, yeah.

Phillip Iscove: It was a mixture of a lot of things. It was a mixture of my love of Tim Burton’s movie. It was a mixture of Twin Peaks. Alex and I both have…we all do, but Alex and I really love the Twin Peaks of it all and wanting to do a show about a weird little town, and how do you do that through the prism of a big network show? It was wanting to do time travel and not do time travel, you know.

Pete D’Alessandro: Right, and that’s a great insight, is you get a lot of leeway out of that and you don’t have any of the consequences of time travel in the show.

Phillip Iscove: Yeah. Yes, absolutely, absolutely.

Pete D’Alessandro: Yeah, that’s a fantastic marriage right there.

Phillip Iscove: Yeah. I can't tell you how sort of…to sit in that room with Alex and Bob and to just immediately have them just like click and get it and be like, “We can do this and we can do this,” and all of a sudden within a matter of moments I'm like, “There's a television show here.” I came in with a thing, which was like Ichabod Crane wakes up in 2013 and he's paired with a female cop and they solve supernatural crimes. It's Buffy meets The X-Files. And they're like, “Yeah! But what if there's The Four Horsemen of the Apocalypse,” [laughs] “and what if he's from the Revolutionary War?” And I was like, “And that is another way to go about it,” [laughs] “and it's probably a far more successful way.”

Pete D’Alessandro: Wow. Well, those elements all wind up in there. I mean, none of that gets lost.

Phillip Iscove: Exactly. And that was the thing. They looked at this idea and we all kind of found a way to quite frankly inject steroids into it.

Pete D’Alessandro: So what was it like when you were actually writing that first pilot? Were you sitting there with them? How were you guys doing that?

Phillip Iscove: They're very busy guys, I don’t need to say that, so it was definitely a…there was a time where I was talking to Alex every day where he would call me and he would say, “Hey, so look at this idea. What do you think of this idea and what do you think of this?” And obviously they're all awesome ideas, [laughs] so it was a lot of me being like, “Yeah, that’s awesome,” and “Yeah, we should do that.” It wasn’t a whole lot of me smacking down his ideas, obviously, because there was no reason to. I think it was definitely more they would sort of go off, they would do their thing and we'd reconvene and we'd talk about those things, and then… It was much more of a sort of solitary…it was like alone together time, I guess is one way of putting it, where you sort of have like everyone’s kind of off doing their thing and now we bring it together and we see how it all kind of works, you know?

Pete D’Alessandro: Mm-hmm. Sure, okay. So, I mean, you're almost…you're on writer’s room for the beginning of that.

Phillip Iscove: Yeah, absolutely. I mean, especially when you have, you know, you've got Bob, Alex, Len, you have Heather Kaden as well who works over at Bob and Alex’s company, you have Aaron Baiers who works over at Bob and Alex’s company, and so all of a sudden it's like, “Oh wait, we've got like six people in this room now,” you know what I mean? So it does become a mini writer’s room in its own way.

Pete D’Alessandro: So what is your writer’s room like now?

Phillip Iscove: What is our writer’s room like now? As you know, I'd never been on a television show before, but it's a very sort of…first of all, everyone in the room is so superbly talented. I find myself just sort of in awe more days than not where I’d sit there and I'd just listen to these phenomenal ideas being bounced around and everyone’s so…everyone just loves the show, you know what I mean?

And it's like, it's such a fun sandbox to play in. It's a hard show to make though. It's a big show. It's an expensive show and the scope of the show is quite large. We now live in a television spectrum or a television environment where people have sort of like movie expectations of television shows, which is great and also daunting, you know? As a viewer, it doesn’t get any better than sitting down to watch Game of Thrones on a weekly basis and be like, “Dear God, how did they make that?” You know what I mean? Like it's just the sheer force of nature that already shows nowadays, it's really impressive, and we're trying to throw our hat into that ring and make sure that we meet a standard that we've set for ourselves, which is to make sure that we send people on a really big fun ride every week. And that, sometimes it's a tall order… [Laughs]

Pete D’Alessandro: Wow. Yeah. So I was going to ask about some of the changes that happened along the way, especially for the pilot. I got to read the pilot script but it's not quite the same as what’s on the air.

Phillip Iscove: No.

Pete D’Alessandro: There's more…much more involved with…there's much more involvement from Crane’s son, the Horsemen are a little bit more present, and there are big effects scenes that I have to assume probably didn't make it for budgetary reasons or…

Phillip Iscove: Mm-hmm.

Pete D’Alessandro: But what are some of the other changes you guys went through? What else did you guys wind up changing?

Phillip Iscove: Well, I think that it was one of those things where, and I think this goes with any pilot and I think this goes with probably…you know, when the writers go off to write it, it's pie in the sky, you know? It's like let's just go big and crazy and bold, and then someone, usually the person who's writing the checks, has to say, “Yeah, you're going to have to shrink this down a little bit. You're going to have to make this a little bit more manageable,” and then it becomes on the writers and the creators to sort of not throw the baby out with the bathwater and find all the stuff that you loved about the earlier drafts and really kind of drill down into that and find out, you know, why did we love this and how can we make this work under these circumstances? I think that any great artist needs restraint and needs to have a box, you know what I mean? Otherwise, I don't know. Personally speaking, I think you need to have restrictions. Without restrictions, I personally think it's very hard to write ‘cause you just do whatever you want, which I guess there are some people in this industry that have that pleasure, but I think that…it's a longwinded answer to your question but I think that, ultimately it was really just sort of a matter of whittling it down to its essence. I think that’s every pilot script. I mean, we went through many, many, many drafts, and it was about finding that key, where's that sweet spot of the show, and I think we found it.

Pete D’Alessandro: So speaking of that box and those constraints, what is your schedule like when you're in the middle of shooting?

Phillip Iscove: I mean, I think that right now we're shooting Episode 12 of 18 and we're breaking Episode 16 right now, so we're in it, you know what I mean? But there's a light at the end of the tunnel. It definitely feels like, you know, if you'd asked me that question two, three months ago, you'd have gotten a very different answer. But I think when we're in the tall grass and when we're in it and it's…it's hard. I think any television show is difficult to make on some level. I think that that's just sort of the nature of the beast. Everyone says that once…I think it was Matt Weiner, he's quoting someone else but Matt Weiner had a great quote where he said, “Writing for television is like a pie-eating contest where the prize is more pie.” I think that’s really very succinct. [Laughs]

I think someone else said, “I loved having written as opposed to actually writing.” I think that that’s probably true for most writers as well. I think that it's everyone likes to look back with rose-colored glasses. I think that's how most people live their lives. So I think that when you're in it, it can feel incredibly overwhelming. But then you look back on it and you say, “Yeah, but it wasn’t that bad.” [Laughs] It was, you know, “Look at this amazing episode that we made,” or “Look at this amazing season we made.” I look at our fans and I look at the crazy amount of support that we have for this show.I just feel incredibly lucky and blessed to have all these people supporting it.

Pete D’Alessandro: Sure. I mean, this year you would have gone through your first hiatus and, I mean, did that actually happen or did you not get to even catch up on sleep?

Phillip Iscove: No, no, no. I think we all got a bit of a hiatus, which was nice. So some of us got a little bit more than others just based on scheduling and what have you, but I think that it was great. I mean, I'm not going to lie, hiatus is a pretty great thing, but I think that also everyone sort of…you don’t want to sit on your laurels too much. You want to make sure that you're still kind of thinking about either the upcoming season or what’s the next show or just quite frankly just sit back and read some books and get inspired by other things, you know, read some books or watch movies or TV or listen to music, like just try to sort of let that time kind of wash over you a little bit and make sure that you're not…you know, obviously you want to relax and have a vacation, but at the same time I personally tried to sort of get as much out of it as I could.

Pete D’Alessandro: Sure, yeah. The other thing I wanted to…I was thinking about you have this position where you sold this one show and you've got the position of having to hire a writer’s room full of writers. So what was that like? Who were you looking for and how did you decide on who you decided?

Phillip Iscove: I think that, first and foremost, it certainly wasn’t on me to make those decisions. I think that it was a group effort entirely. Our first season, it was Bob, Alex, me, Heather, Aaron. We were all involved in the entire process. And then Mark Goffman is our showrunner now and he obviously was very much involved in the process between Seasons 1 and 2. I would just say that as someone who's been at an agency and sort of set up those staffing meetings, and then to then be on the other side of it, I think it's all about like, well, first and foremost, it's obviously the sample, right? You read their work and if you like their writing, then you take the time to sit down with them. But I would say that it was really sort of, you know, as I said, the show’s a bit of a high-wire act, so it's really just kind of finding the right samples that feel like our show, and then you sit down with them and you talk to them about how do they see the show and what kind of show do you think it is, what kind of episodes would you want to write, and you really just kind of hope that you're creating a hive mind of sorts and make sure that you're picking people that feel like they understand what the show is and what you hope the show is going to be. It's a lot of wish fulfillment, [laughs] quite frankly. It's a lot of just sitting back and hoping and praying that you're picking the right people.

Pete D’Alessandro: Sure, okay. Well, Phillip, I know we have to wrap it up, but thank you so much for joining us.

Phillip Iscove: Of course, of course.

Pete D’Alessandro: And congrats on the show, congrats on the second season, still a big fan myself, so I'm really enjoying it.

Phillip Iscove: Oh, thank you so much. I'm so glad that you're liking it.

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