Richard Shepard Walks Us Through Directing the ‘Zoey’s Extraordinary Playlist’ Pilot

Zoey’s Extraordinary Playlist is a big ol’ ball of delightfulness. The NBC musical series has a magical premise, in which Zoey (Jane Levy) hears others’ inner thoughts through song. It’s a comedy with the sweet and the sour, plus ambitious song and dance numbers.

With its huge musical number in the streets of San Francisco and classic songs that don’t come cheap, the pilot episode establishes that Zoey’s Extraordinary Playlist isn’t your average network programing. It was directed by Richard Shepard, who’s no stranger to setting the tone and style for shows. In addition to making such feature films as The Matador and Netflix’s The Perfection, he helmed the first episodes of Criminal Minds and Ugly Betty, as well as the premiere of the next season of American Crime Story.

We talked to Shepard about the process of directing a television pilot and specifically what the pilot of Zoey’s Extraordinary Playlist entailed.

What is the appeal of directing pilots?

Getting to direct pilots is like a dream job for anyone who’s in the television business as a director. Because as a pilot director, you get to shape the look of the show and the tone of the show. You get weeks, if not months, to help hone the script and to figure out the cast and to really work to create this thing.

You also get a piece of the pie. You get a check every time a new episode is made because of the Director’s Guild. As I said, you can do the pilot and then never have to work on the show again and you’re still getting a little taste every week. So, it’s the dream job. It can be an incredibly tough business to get into.

The studios and networks are making ten to twelve drama pilots, and they’re spending anywhere from six to ten million dollars on each of them, so they’re wasting a huge amount of money. I think it’s such a weird fucking business. You know, there are all these pilots that millions and millions of dollars have been spent on that just never see the light of day. So they are obviously very particular about who they hire. I’ve made some independent films and thought that I should do a pilot and never could quite get into it.

How’d you get your foot in that door?

After The Matador, the executive producer of that movie — a guy named Mark Gordon — had a director drop out of Criminal Minds, the pilot, four weeks before they were going to shoot. They were looking for someone unique or different. He put my name out for it. I remember very specifically everyone said no to me because I had barely done any television at that point and I certainly hadn’t done anything that anyone had seen. The Matador hadn’t come out yet. Mark Gordon pushed me through the system and that was my first pilot.

It ended up obviously turning into a huge big hit TV series, but it also was, at the time, I think, a really cool looking pilot. It suddenly opened all the doors for me that would never have been opened without Mark Gordon pushing me through the system. From there, the next pilot I did was Ugly Betty, which was about as far from Criminal Minds as you could possibly get. But that was something I really wanted to do. I remember being sent six pilots, and I remember my agent at the time said, “Do any of these except Ugly Betty.” That was the one I fell in love with, so I did it. Like all the pilots I’ve done, it’s a very close collaborative process with the writer-showrunner, because he or she has been laboring over this for possibly years and I’m coming in at the last minute now to make it three dimensional, to make it real.

So it’s about keeping the faith and thinking about it for over a year and now trying to visualize it in a way that’s actually hopefully an improvement even on how they’ve been thinking about it. In a weird way, it’s incredible collaboration in which, ultimately, it’s the writer’s decision, not the director. In television, the writer is the power. But if you’re working in a deeply close relationship like I’ve been able to do on my pilots, you end up really collaborating and you get to create a vision for the show that hopefully exceeds the dreams of the writer to begin with.

You have to do it quickly; you have to have a planned vision. It’s not like season six of a TV show that is like a machine that just generates week after week. It’s basically a movie you’re making with very little money, so it always suited me really well. Not really being part of the development of the script and then coming in a month or two before you shoot with fresh eyes has always really been good. I’ve been able to take apart the script, not necessarily in a negative way but just ask questions that now need real answers. It’s figuring out ways to make things visual and how to condense stuff and how to legitimately figure out the character, cast, one-line description. Figuring out what clothes they’re wearing, where they live, and all of that stuff.

To me, it’s a huge amount of thought.

As a competitive person, it’s a really strange thing. A normal network pilot will be greenlit at the beginning of January. Then by the beginning of May, they make their decisions on which ones they’re picking up. So there’s a three-month scramble basically to get the best pilot out the gate and to beat all the other ten or twelve pilots that are being done for that network.

They pick them up or they don’t. If they pick it up, you’ve done your job. You succeed. In independent films, a lot of times it’s hard to get distribution. Your movie barely opens. Or at least these are my movies that barely opened. In general, this idea of not quite getting a moment where you feel like you’ve crossed the finish line, in TV pilots you really do get that. That’s what I really enjoy.

What were some of the questions you had for Zoey’s Extraordinary Playlist? Where did your work start?

The first thing is that often we start with a really great script. From our very first meeting, we really hit it off. The question really is about tone. How can we keep this grounded while something very insane is going on? How do we make it relatable to people? How do we make it fun and breezy but also allow the humanity and the emotion to come in? Because the script has a lot of that. These are questions that a lot of time is spent discussing it.

A lot of time is spent discussing the cost, and then the choreographer, Mandy Moore, may do more. Just discussing how are we doing the musical numbers. Are they looking in the camera like in normal musical numbers? Are we doing a lot of cutting like a music video? Or are we going to do it in a way in which the movement makes sense for Zoey and makes sense for the emotion of what we’re trying to show? A huge amount of time was spent on that.

Often I joke because simple things, like, “What’s in Zoey’s apartment? What are on the walls? What is on her desk?” These kinds of questions are crazy but they have to be answered. There has to be something on her wall and there has to be something on her desk. So if we can just find some specifics that help define her character, that will make it all more tangible.

It’s not so easy because you have to dig a little deeper even then for the idea you have in your head. So, I ask these questions. I ask a huge amount of questions. I do my best not to drive the showrunner crazy. But in Zoey’s Playlist, this is a monumental undertaking. We were going to shoot in Vancouver, but we were also going to shoot for a few days in San Francisco. We had to deal with recording the songs, choreography to the songs, and the orchestration of the songs. Then we also had to build an incredible set and find a space that we bring the set. So there was just a lot of stuff. There were certain days where you’re like, “We’re never going to get there.” [Laughs] Then somehow you do.

What is most thrilling about putting together a musical number?

Well, I was super excited to be able to do a musical. I have always really wanted to do one. I had done a musical number on an episode of 30 Rock and I had done a little number on the show Girls that I directed a lot of. But I had never done a full-blown five or six song musical like Zoey’s was. So it was truly exciting. As soon as Austin and I won the fight to let us shoot in San Francisco, we really knew we had to show San Francisco or the people paying for the show were not going to be happy.

Then I started to figure out how we were going to do the stuff we wanted to do, which was to have longer takes and not a lot of cuts. To make it feel like it would be this type of number you could do in a feature film as opposed to just a television show. We also knew that because Zoey is such a specific show, we knew this was going to be used in the advertising if the show got picked up.

So it was a huge amount of pre-planning. I was working seven days a week while we were shooting. On the weekends, Mandy and Austin and I would fly to San Francisco with our AD or DP and figure out exactly how we were going to shoot it. Then we’d fly back to Vancouver to shoot the normal week and then we’d fly back again because you need to prep and all of that stuff. Had it been pouring rain, we probably would not be talking about Zoey’s Playlist. It was the last two days of the show, we had finished our Vancouver work. We flew down there and the whole entire sequence was planned as if it was not raining. We didn’t have a backup plan. It’s one of those crazy things where the TV gods are looking out for you.

I’ve been in other situations where it’s pouring rain and we’re really soaked. But thankfully, we did not encounter that.

When you’re directing a pilot, what’s the collaboration with a major network like?

You have to ask for things, and you can will them to happen in a weird way. I think one of the reasons I continue to work is that I’m someone who, I come in on schedule and I come in on budget as best I can and I’m not out of my mind when it comes to that stuff. I think the studio had an understanding that I was being realistic about what I was tasked to do. But when I said, “Listen, I’d love to shoot in North Beach and I’d love to be on Broadway and I’d love to fill the little park in the middle of the street to do a musical number at the beginning.” People are like, “There’s no way that can happen.”

Then you just keep repeating it. At some point, they’re like, “There’s no way you can shoot on a Sunday.” Then at some point, the production manager says, “Well you know we could shoot on a Sunday.” Then suddenly it happens because, on the production side, they look for solutions and try and give the people what they want if they can do it. So we did it. It was crazy, but on that Sunday that we were shooting in North Beach in this colorful part of the town, we got the whole street and I was like, “I can’t believe this.”

We rehearsed the day before in a parking lot in San Francisco. We basically built that little area where everyone’s sitting in the beginning of the number. We’ve done it in a parking lot. We rehearsed it with the camera and figured out exactly how we were going to shoot it because we couldn’t even begin to build it until the Sunday morning of the day that we were shooting. So Sunday morning, 7:00 am, they started building that little shooting area while we shot some other stuff. Then at 11:00 am we came. Because we rehearsed it the day before, we shot the first forty seconds of the song in a oner in, you know, an hour. It was one of those things because we knew what we were doing. The whole number took a day when you piece it all together. I think the sense of victory was huge when we were done.

The musical number between Peter Gallagher and Jane Levy, there are not as many extras and you’re indoors, but is it as complicated as a musical number in the streets of San Francisco?

Weirdly, it’s almost harder. Help is so big. At a certain point, we all were sitting there looking at the monitor. If the dance works, it works, and if it doesn’t work, it doesn’t work. There’s not really a question mark. It either works or it doesn’t. It’s almost like a stunt. A stunt either works or it doesn’t. Dance sequences are a little bit like that. The scene with Peter Gallagher and Jane was such an emotional scene that, for our sake, we thought about sweeping everything away. Then it was just really about allowing those actors to be as honest as they could. So I’m in a situation where we had recorded Peter Gallagher’s singing “True Colors,” but I wanted to record it live on the day as well. We had it in our back pocket in case he lost his voice or couldn’t do anything.

Basically, that’s him singing live. It added such humanity to the whole thing. It was so personal. It was very difficult. It was a small space and Jane is crying and Peter is… It’s not easy. In a way, thirty dancers jumping in the air down a street in San Francisco is weirdly easier than that. One of the things I think that attracted people like Peter Gallagher and Jane Levy to the project was the fact that the show has such a different scope. It can be big and fun and bouncy and it can also be very emotional. I think that to me is a sweet spot in terms of what I love to do. I love comedy and drama and I love it when it can mix together.

I think that sometimes it’s easier to do a simple drama. The stuff that mixes tones is just harder, but it’s always been something that I’ve been attracted to. Maybe because it is difficult, but also because it’s still a lot more like life. In life, even in the most dramatic moments, there is humor. And even in the funniest moments, sometimes there’s sadness. So to me, that feels a lot more real. It’s a difficult tone in general and film and TV is a tough nut.

Working with very charismatic actors like Jane Levy or America Ferrera, do you think, “How can I best communicate their charisma with the camera?”

You do. Listen, with America and with Jane, you’re talking about two outstanding actors who are coming in basically ready to go. My job as a director always is to ensure that the other actors around them were up the shelf.

We’ve rehearsed it and discussed it and there’s a level of comfort. But I will do a bunch of takes. Someone like Jane will do a take that’s very big and a take that’s very small and everywhere in between. In a pilot, I encourage that a lot. Let’s see what really ends up working in the editing room, because we may need to make this funnier, we may feel like it’s too silly when we play it back. So we did do a lot of variances of stuff.

At the end of the day, one of the pleasures of being a director is between action and cut, because the actors get to just suddenly make it real. If they’re doing their job, which they usually are, then you look good as a director without doing much. You set them in a beautiful place and then they do the beautiful work. I find that when I’m directing actors, it’s usually when it’s a child or a dog, that’s when you’re really directing. How do you get a child to do something? With a really good actor, they’re doing ninety-five to ninety-nine percent of it. In Jane’s case, we were in love with her after the first day of shooting. We were like, “Holy, shit, she’s so good.” I was like, “This shit is awesome. The show is going to work. She is unbelievable.” That’s the hardest part of the show. If she is not great, it doesn’t matter how good the musical numbers are. She just killed it.

When you’re directing a pilot, do you get to have much say about casting?

Occasionally an actor will be attached. When I did Ringer, Sarah Michelle Gellar was already attached. On Ugly Betty, they were circling America but the deal hadn’t quite closed yet. With Zoey’s, no one was cast. So part of what I love about it is to be able to sit with the writer and bat around who would be great for this. Then you find out who’s available and who’s interested. Sometimes you get really lucky. Jane Levy was someone who we all were like, “We should go out for Jane Levy.” We didn’t know whether she could do it. We were fans of hers. So sometimes you just have an instinct about an actor and then you meet them and they get to show that they understand what the show is.

On TV pilots, sometimes you replace actors. It happens more than you would imagine, in which a pilot is shot and then they’re like, “We love this pilot but we can’t find the boyfriend. He’s walked away.” They’ll need to re-shoot this. It happens a lot. Because you are basically casting, not even quite sure what the show is yet. Then you do the show and you’re like, “This show is much funnier than we ever thought but the guy playing the boyfriend isn’t that funny.”

A part of what your job is as a director is trying to really think twelve steps ahead. Can we find an actor who can be both funny and dramatic? Then we shoot them both funny and sometimes dramatic. So that in the editing room if we’re feeling like they’re not going to do it then we don’t have to replace them. We don’t have to do all of that. We can get the show kicked off. Listen, it’s happened. I’ve directed reshoots on almost all of the pilots I’ve ever done.

Is it assumed with most pilots that reshoots will happen?

When we’re shooting a pilot, there’s no discussion of reshoots. It’s really a discussion of, can we just get this done with the cast that we have? So let’s say you did the pilot in March and it gets picked up in April and May and now they’re going to start shooting in July, the first few days of July will be spent reshooting the few days worth of footage of the boyfriend. It becomes part of the schedule of the show.

If the director of the pilot is available then he or she flies off to Vancouver or wherever they’re shooting the show and you direct those two days on a reshoot. Sometimes they replace an actor because the show got picked up and now they want a bigger star for that supporting role. Like, it’s the grandpa. The grandpa in the pilot is an actor that we could get for ten grand and now the show’s been picked up, and suddenly, there’s more money so we can afford to get this type of actor.

That must be a hard choice, too.

It’s heartbreaking every time that it happens. I heard a story early on about an actor who was cut out of a movie and not told by the director and brought his parents to the fucking premiere. You have to have a big heart as a director, for actors because it’s the only job on a film set I couldn’t do myself. If someone said, “You have to light the show,” I could light it. It wouldn’t be very good but I could light it. If they said, “You have to give the sound,” I could figure out how to do the sound. But I can’t act.

I have no capacity to find that openness that actors do, the real vulnerability they have to be able to access. So when someone gets replaced as an actor it’s heartbreaking. It also happens. They move on and they get another job and they forget about it.

The show is so appealing to the eye. What kind of feeling did you want to evoke with the aesthetic?

I wanted to make it bright and accessible without it feeling like a sitcom. I wanted it to be able to be magical without ever having to do anything magical to the show. We were like, “Should we change the lighting? Should we do this?” These are a lot of conversations that happened prior. Then there are the musical numbers. It was about building roles that visually could go into beautiful canvas without it ever really changing. A lot of that was just from the learning curve. There were certain shots that I did in the pilot of Zoey that didn’t make it into the finished product. They were a little too raw. Suddenly the lens is too wide and it feels a little too much like we’re stepping back from the motion and talking about it from a different point-of-view, from the director’s point-of-view. So we chose not to use that shot.

I imagine these pilots give you the financial freedom to go make movies like Dom Hemingway or The Matador. Do pilots allow you to only make the original movies you want to make?

I am so lucky. I have never had to make a movie I didn’t want to make, but I also don’t make my living through my movies. Because they’re so cheap, though, I’m able to make them and I’m very thankful for it. The role of directing pilots has allowed me to make short films and documentaries and take a year off to make a movie and all of this stuff. It has afforded me that lifestyle, which is very specific to who I am as an artist. I can go out and make a thirty-minute short film in Tokyo, which I did two years ago. We ended up selling it to HBO and Lizzy Moss was in it. I’m really proud of it. It’s called Tokyo Project. I just wanted to have that experience. From that experience, I learned and it affected my future work and all of that.

There’s no television right now, but listen, when COVID is done we are in a moment where there is a lot of TV being produced. They are finally starting to hire people of color and women and other people who for years, decades, have been kind of excluded from TV because of this overprotective world where they’re worried about, “Oh my God, they just did one independent movie. Can they direct a TV pilot that we’re spending ten million on?” That feeling has led to a lot of, I don’t want to say racism and sexism, but I’ll just say that it has led to a lot of non-creative choices for people who direct pilots.

Now that we’re in a brave new world of understanding, they are letting people direct pilots who aren’t necessarily with a huge resume behind them. We’re going to see more and more interesting stuff because there’s just a huge amount of interesting voices out there who should be able to be making movies and television.

For me, I’m always thankful every year if I get offered a pilot that I like to do. That for me is like, wow, this is simply another year that I’m going to get to have this experience. Believe me, I’ve done pilots that have not been picked up. I’ve done more pilots that have been picked up than not picked up, thankfully. Zoey was the year that I did three pilots and [only] one of them got picked up. But in our business, it’s just completely anonymous. No one knows.

Jack Giroux: Longtime FSR contributor Jack Giroux likes movies. He thinks they're swell.