Payton Russell

A conversation with showrunner Alex Gregory.

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“I’d like a black cold brew and overnight oats.”

If I told you a highly successful person ordered this at a fancy breakfast place, who would you think of? Gwyneth Paltrow, probably, depending on the serving size. Martha Stewart if it comes with a side of financial fraud, or Nikki Glaser if she has a night of anal ahead and needs to clear out. 

Having brunched across from a lot of writers with less-than-stellar eating habits, this order from writer and showrunner, Alex Gregory, surprised me – you’re telling me writers can be funny, smart, and healthy, too?

When asked about the differences between TV and feature writing, Alex says that one of the most important things he’s learned in TV so far is to be a “good hang”. Understanding how a room works, knowing room etiquette, and being pleasant to be around is part of the job – and from what I’ve seen from Alex, that starts with a heart-happy breakfast.

Across his career so far, Alex has written on a number of popular shows, including the Late Show with David Letterman, The Larry Sanders Show, Frasier, King of the Hill, The Tracy Morgan Show, and Veep. He also co-created White House Plumbers and the Emmy-winning series, The Studio. 

Alex also wrote and directed the star-studded film, A Good Old-Fashioned Orgy, which I force him to talk about below. Collaborating often with his closest friends, Alex has made a name for himself in both industry comedy circles and in households worldwide. At Austin Film Festival, we met between panels to talk story, structure, good coffee, and even good-er jokes.

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A Good Old-Fashioned Orgy

Payton Russell (PR): In prepping for this, I spent a night watching the 2011 classic: A Good Old-Fashioned Orgy, and it was a lot more heart-warming than expected. There was even a point where I wondered if there was actually going to be an orgy. Was there ever a version without it?

Alex Gregory (AG): That film is a bit of a feathered fish—not a full-on raunchy comedy, but also not a sweet, chaste coming-of-age story. It’s kind of in the middle. We went through various incarnations of the script, and there were moments where the orgy didn’t happen. But we felt that version was so unsatisfying—it would feel like such a rip-off. Ultimately, the movie was about vulnerability and emotional honesty. To really feel close to someone is to let your guard down, and that’s what happens at the end: the protagonist’s guard finally comes down, which allows everyone to really connect and be silly.

PR: How did the idea for this come about?

AG: You want the full story? A friend of a friend of ours had been to a party in the Hollywood Hills, and he said, “After I left, I heard an orgy broke out.” We were like, “Bullshit.” He said, “Why would I lie about that?” And we said, “People of our generation don’t have orgies.” The more we thought about how impossible it would be, the more we realized that could actually be an interesting movie. So, we wrote a version of it and gave it to our agent. We were really excited, and he said, “Put this in a desk drawer and don’t ever show this to anyone. This could end your career.”

PR: Lol. What was his reasoning? 

AG: Oh, it was offensive, it was bad, it was low-budget—it checked every conceivable box of what you shouldn’t do. Eventually, our manager got it to Vince Vaughn, and we did a bunch of rewrites with him. They were super fun—he was really, really smart about it—and he gave us the best note possible: “If you want to make something universal, make it very specific”. So, we started including a lot of personal details, and it changed. We kept writing it over the years. Then I got married and had kids, and the married parent characters (Will Forte and Lucy Punch) evolved from being the villains who are trying to sabotage the orgy to the couple who are hurt that they weren’t invited and try unsuccessfully to crash it.

PR: In this project or others, do you ever take into consideration what’s kosher to joke about, or what the audience might get offended by?

AG: Yes, but it’s rarely a discussion of “Is this offensive?” because I don’t think any of us at The Studio are trying to hurt anyone’s feelings or do anything just for shock value. On Veep, every joke was pushed as far as it could go, but the contract we had with the audience was clear: “We’re going for this. This is an Anne Frank joke—are you cool with that?Because that’s where we’re going.” The audience of Veep understood that’s what they were signing up for.

The Studio

PR: Having worked at HBO and seen so many potential characters within that studio environment, I was curious how you guys settled on the character of “Matt Remick” and his particular team in a cast of only five or six central characters.

AG: Because Seth and Evan have their own production company and have made big movies, they got a really good window into how the other side lives. In a way, it’s similar to what we did with Veep. Matt Walsh’s character (Mike McLintock) would, in reality, be ten people. He was compressed into one—somehow, he’s in charge of the press and speechwriting, which would never happen.

So, in a way, each of The Studio’s characters represents a department. Ike is production. Catherine handles marketing crises. Seth decides which movies get made. And Quinn represents the young people coming in at a time when all they hear is, “Movies are dead!” Her dream is basically to be Matt. So, we narrowed it down to those key elements.

PR: One of my favorite episodes was “Pediatric Oncologist.” I was curious if you could talk about how that episode was broken and the decision to pull Matt away from the main cast for almost an entire episode?

AG: It started with all of us collectively deciding it’d be fun to see Matt date someone where he has no currency. Because he’s a studio head—if he’s dating anyone in the industry, they’d know what he does and respect him. We decided to take him out of his comfort zone—somewhere no one knows or even cares what he does, somewhere he’s really on his heels and defensive because he’s so used to being in a position of power. I just blurted out, “Pediatric oncologist!” It was one of the ideas we pitched to Apple in the room, and it just stuck.

Seth had been to a bunch of these medical banquets because he’s a famous person, and he said every time he goes; the doctors go out of their way to tell him what he does isn’t important. Seth thought we should set the whole thing at one of those banquets. From there, it was about figuring out the stakes: he has to choose between ego and love. If he can swallow his pride and admit what he does isn’t that important—or even just say it without believing it—he has a chance at love with this beautiful, intelligent, accomplished woman. But he can’t do it. That’s what the episode is about.

We specifically set out to do a personal-stakes episode. It was us consciously expanding the world, same as “The War,” which focused on Sal and Quinn’s fight. That was about showing other people in the world. “Pediatric Oncologist” asked: What’s Matt’s inner life? Does he date? That’s how we answered why he’s alone. Even when developing the show, we never once thought he was married—we knew he’s either divorced or single. There’s no way this man has love in his life, because for the mechanics of the show to work, the job had to be everything. If he went home to a wife and kids, he’d have perspective. So, that episode was a combination of Seth’s experience and also my experience.

PR: What was your experience?

AG: My daughters were born very prematurely, so we had a lot of doctors and surgeons—horrific stuff. A Good Old-Fashioned Orgy actually plays into this, because, while I’m dealing with a daughter having surgery, I’m having a knock-down, drag-out argument over whether a fake penis flopping down in a frame seems too broad. I’m screaming about the dick flop in the hospital. That scene in The Studio where Matt and Sarah walk into the banquet, she’s talking to parents who think their daughter might die, and he’s talking about juicy farts—that’s my whole view on what we do in one scene. If someone asked me, what scene is you? That scene. The stuff Sarah is talking about is harrowing, not funny in any way, shape or form, and in fact, the more harrowing it is, the better it worked. There are moments where it’s really painful for her, and he’s talking about Rotten Tomatoes.

PR: For the oner episode, what was the hardest part of that episode to achieve?

AG: The oner was amazing. It was as much a triumph of logistics as of art, because our AD had to schedule each day around the sun. It’s not a true oner, but we had to match light. Because, if you’re going outside, we have to shoot the other bit at the exact same time of day. We had to rehearse and back-time everything to the light, which was hard. If there had been one rainy day—

PR: Were there rainy days?

AG: Thankfully, no. But that last shot of the episode where they’re running out of light—we were literally running out of light. The episode was mirroring what was actually happening. We were thinking: This is it. This is our last shot. And they got it.

PR: With Season Two—you probably can’t talk specifics—but when you’re approaching a new season, are there hard-and-fast rules about how to introduce new characters or a new premise? Or do you just hop back in as if it’s another episode tacked on to the end?

AG: We were thinking about time passing – How much time has passed? Are we picking up right where we left off? Are we going to see what happens with The Kool-Aid Movie, and will that impact the season? Because our show isn’t tightly serialized, there’s not a lot of pressure to figure that out.

PR: With a show like The Studio where it’s not tightly serialized, do you have to come up with a new problem for each season? 

AG: Yes. The first season was about him, ostensibly, keeping his job. Season Two isn’t about that. Without saying what the problem is… [Season Two] is about something else—something more personal. The fun thing is, now that you know all this about him, you can hit the ground running with more of a shorthand. We know his dating history and how he feels about that, so we can explore other areas and really dig in.

PR: I’ve only ever been in a drama room, so I’m curious—in comedy, during the blue-sky phase where you’re just coming up with ideas for episodes—how long does that last? And how many ideas end up on the board?

AG: It usually lasts a few weeks because you almost want to exhaust every possibility and then pick the best ones. Veep [under David Mandel] was more specific – the plan was always: what’s the final shot of the season? Then, we’d reverse engineer the entire season. If we’re ending here, how do we get there? It’s not a bad method for how to engineer a season. King of the Hill was different – we’d pick a thing that’s going to happen, like “Hank goes to Japan and finds out he has a brother”, but it’s not the whole arc of the season. So, outside of that one thing, we asked – what’s an interesting, funny episode? The episodes were based on a lot of personal stories that came up in the room, or things we’d heard about.

PR: For each episode, are you pitching beginning, middle and end, or are you just pitching something super simple?

AG: It’s always something super simple that ideally lends itself to something visual and active. Then you go, “Okay, how do we get there—or where do we go from there?”

Comedy Industry

PR: How have you seen the TV world change over the years—specifically TV comedy, and also TV overall?

AG: It’s funny. I’ve had the same agent since 1995, and he was lamenting the state of the industry, talking about how great it was in the ’90s. And all I could think was: I wouldn’t go back with a gun to my head. There’s always a flip side to everything. Yes, the business now requires an unprecedented level of hustle, but the quality of work being done is also unprecedented.

So, if you care about quality, this is a good time to be in the business—it’s just hard. There was a time when, once you got in the door and on staff, you could just work. It was stable. But at the same time, there were only two or three really good shows. You’d spend a lot of your career working on mediocre stuff and being grateful for it. Now, stuff out there is good. Somebody Somewhere—would that have gotten on the air in the ’90s? No.

So, the way I see it—and what would I tell young people—is: all these headlines are great because they’re keeping people away. The last thing you want to be doing is follow a herd into a gold rush, because then everyone’s vying for the same shit. Let everyone else go to social media and Instagram. If you want to make cool shit, this is still the place to do it.