How ‘Jury Duty’ Director Jake Szymanski Pulled Off the Longest Con in TV History

Amazon Freevee
Amazon Freevee

Director Jake Szymanski came up at Funny or Die and Saturday Night Live, but nothing he had ever done in the comedy world could have prepared him to pull off what was essentially a real-life version of The Truman Show, with jokes, on Jury Duty.

In this episode of The Last Laugh podcast, the director breaks down what went into making the comedy-reality show’s unsuspecting star Ronald Gladden think he was in a documentary about jury duty when he was actually surrounded by actors and improv comedians for three weeks straight. Szymanski reveals how they cast Ronald, the secret maneuvers behind the show’s hilarious Margaritaville episode, and the huge sigh of relief he let out when they finally let the cat out of the bag.

It’s been about two months since the finale of Jury Duty went up on Amazon Freevee and Szymanski is still trying to figure out the best way to describe it. “I’ve heard it called The Rehearsal meets Ted Lasso, which made me chuckle,” he says.

The way the creative team, which included veterans of everything from The Office to Borat, talked about it early on was by asking themselves a question: “What if you were making a show like The Office, but Jim wasn’t an actor and didn’t know it was a TV show?”

Of course, the whole thing hinged on finding the right “real person” to be at the center of the show, and Jury Duty hit it out of the park with Ronald. As Szymanski explains, they enlisted producer Alexis Sampietro, who had worked closely with Sacha Baron Cohen in the past, to put out an ad online looking for people who wanted to participate in what was pitched as a documentary about the U.S. legal system. More than 3,000 people responded.

Sampietro interviewed almost a hundred of them personally before narrowing the list down to her own top 10, which included Ronald. Unlike with Baron Cohen, who actively searches for subjects to humiliate, Szymanski says they were trying to cast someone who could serve as a “moral compass” for the show.

“Ronald submitted a video about himself at first to say why he’d like to do it, and a little about himself,” the director recalls. “And when we got down to the very end, when we had a small group of people we were deciding between, we even had everyone do a little evaluation with a psychologist as well, because we wanted to make sure, since we were doing this experiment that hadn’t been done this way before, that we weren’t picking someone who couldn’t handle it.”

Not only could Ronald handle the situation, he exceeded their expectations at every turn, delivering one of the most compelling TV performances of the year, all without knowing he was performing at all.

Below is an edited excerpt from our conversation. You can listen to the whole thing by subscribing to The Last Laugh on Apple Podcasts, Spotify, Google, Stitcher, Amazon Music, or wherever you get your podcasts, and be the first to hear new episodes when they are released every Tuesday.

Do you remember why Ronald wanted to do this? What made him want to be part of what he thought was a documentary about jury duty?

I think it speaks to his nature. He’s just a curious guy, up for an adventure, up for a new thing. And we found him at the right time where he was just switching jobs, he had saved up a bit of money, and he was planning on taking a couple of months off. And then he saw this opportunity right in his window and he said, “Oh, this is something I’ve never done before, and I might not have the opportunity to do it again, so I’ll sign up for it.”

And how did you know, personally, that he was the right guy? What was it about him that made you think this is the direction you wanted to go?

Well, it’s everything you see in the show about him. You could see it peeking through in his interviews, and you go, this guy seems great. But I will say, I think we’d all be lying a little bit if we said we knew for sure. We really hoped and thought this was the right guy. But we did this for so long, we built this world around him for three weeks, and after the first couple of days, you really don’t know what someone’s going to do. As much as you can look into them and interview them, three weeks is a long time. We hoped and thought Ronald would be great for this, but he was even better. He kept pleasantly surprising us throughout.

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The other piece of casting that I think we have to talk about is the James Marsden piece. Was that always the plan, that you wanted to include one celebrity on the jury?

We always wanted to include one celebrity. That was part of the DNA of the show from the beginning. We didn’t know who would be up for it. And we really hoped James would be.

He was always at the top of the list?

Yeah, we talked to him basically right away. As soon as the show got picked up and we started putting a writers’ room together, and once we knew we were going to keep the celebrity aspect, James was right up there. I had worked with him before in a mockumentary called Tour to Pharmacy. I was really excited about him because James has just been in so much stuff, and he’s so recognizable, but he’s also not Tom Cruise. So it’s kind of a perfect celebrity factor that we needed. But the thing that got me most excited was, I just knew James could be really funny. I came up in the world working with Adam McKay and Will Ferrell, and I was around when they were making Anchorman 2, and Marsden is in that being really funny. I remember everyone whispering like, “James Marsden, he’s really funny, he can really hang in comedy.” But he again, like Ronald, far exceeded our expectations. Because he’s so good at playing this Hollywood-y version of himself. He just knocks it out of the park being in the situation, quick on his feet, doing the improv, hitting our story beats. He was such a pro and really just did even better than we hoped.

It’s so interesting because, as you said, that character has to be the right level of famous, and he has to be willing to make fun of himself in the way that he does on the show. So yeah, now that we’ve seen it, it’s hard to imagine anyone else being the right person for that.

And by the way, he also has to be on board with the spirit of the show we’re doing. And it also has to be someone who understands—and this was important to James as well—we’re not trying to make this guy the butt of the joke. We’re not trying to punch down. We all held ourselves to that standard. Because you could see an opportunity for an easy joke every now and then, but it wouldn’t have been the right type of joke for what we wanted the show to be. And James was an important part of that sounding board process as well every day.

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Once you started production, was there a moment when you really felt like it was going to work, that you were going to be able to pull this off?

That’s tough. Because there were hurdles to jump. Like, let’s see if we can get past this without ruining the show. James Marsden was really the first big hurdle. Let’s see if we can have James walk in, sit next to this guy and strike up a conversation before he thinks, wait a minute… I don’t know if there was ever a point where we thought it’s working for the whole show. There were points where we were like, “Well, we’re going to get through the day.” We were nervous about breaking the show almost every day throughout the filming process. So it really wasn’t until the last two days before we were like, “Well, we’re definitely going to get to the reveal where we get to tell him about this.” It was our first time doing this as well, so at any point Ronald could have said, “Hey, hold on! Something about this isn’t real. This isn’t right.” And we could have two weeks of filming left, and we would just be done. So we were nervous about that every day. I don’t think that we ever lost those nerves.

There’s that great moment where he compares the experience to being on reality TV, which must have raised some eyebrows in the control room.

We were panicking. We all just kind of froze and looked at each other when we heard that and went to Defcon 5 and hit the panic button. “Pull back, pull back! No more jokes!”

You talked about how you worked with some of the same people who had worked with Sacha Baron Cohen in the past. Jury Duty feels very different from what he does in that you’re not trying to embarrass the target. So how do you view what you guys did as different from what someone like Sacha Baron Cohen does?

Well, the thing that I think we did differently, that initially got me interested in the project, is this idea of, can we put someone who’s a regular person, who doesn’t know they’re signing up to be on a TV show, can we give them the traditional hero’s journey? We’re not looking for a target who deserves to be taken down, we’re not looking for someone who’s said some really controversial things and we want to point out hypocrisy. What if we find someone who can be a moral compass reacting to these crazy characters around him and give him a hero’s journey? Someone, if we put him on the path, that will give us that 12 Angry Men moment at the end of the show where they can convince people to go the right way. And it was a risk, but that was the exciting part of the experiment because we haven’t really seen that before. Can we prove that someone will do the right thing? And not only do the right thing, but convince our wacky characters to do the right thing? That was a really cool idea that I thought was worth exploring, even if we fail.

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Which you didn’t. He really did come through in the end, right?

He really did. He came into that deliberation ready to go, ready to tell people how he thought it to go down, and it was just perfect.

As you got closer to the finale, the pressure obviously mounted in some ways because you really are feeling like, “Maybe we can pull this off.” What did it feel like for you, watching that moment when you finally do reveal what’s happening? Because it is so intense watching it as a viewer, and I can’t even imagine what it was like for you as the director.

It was nerve-racking. It was very intense, especially because we all just cared so much about Ronald at that point. It was always in the plan to be really thoughtful and careful about how we were going to reveal this, but it didn’t mean we knew how it was gonna go. And we were all very nervous about, are we doing this the right way? Is there a better way to do it? I think we were rewriting that judge’s speech every night leading up to that reveal for the last week of shooting. Everyone had tears in their eyes and lumps in their throats as it was happening, and we just really wanted to pull the curtain back and reveal what was happening, and then also surround Ronald with a bunch of love as fast as we could to let him know that everyone really cared about him.

How did you think he was going to react to that moment? And how did it compare to what actually happened?

We were prepared for a lot of things, and I think we expected maybe a bigger reaction. But what we forgot is that when you’re three weeks into creating a Truman Show-esque world around someone, it’s really hard to tell them that it was constructed and everyone’s an actor and have them understand that right away, which in hindsight makes a lot of sense.

Seems like he might be in shock.

Yeah, so I actually think we were preparing for a bigger reaction from him. Is he going to be upset? Is he going to be happy? Is he going to get up out of his chair and move around? Let’s have the cameras ready. But I think he really had to sit there and process it to even understand what we said, because that’s a big thing to tell someone. I want you to think about the last two and a half weeks of your life and realize that everything has been planned and all those people were actors and were in on this thing surrounding you. That’s really hard to understand. You have to think a lot about what happened in the last two, three weeks to you. So there was a lot of processing. That seems obvious now, but we maybe didn’t fully comprehend what was going to be needed there.

What have your conversations with Ronald been like since then, in terms of how he felt and what he thought about the whole thing?

It’s been great. I mean, for me personally, I didn’t meet Ronald until after the reveal. So it was a bizarre experience for me and Ronald, because I felt like I really knew him, and I had been watching him 20 hours a day for the last three weeks. I’d seen all these interviews he had given beforehand, I had been thinking about him and planning stuff around him. And I came out and introduced myself, but I had to realize I had a level of comfort with him that I needed to pull back. I knew him really well, I felt, but he didn’t know me. So personally, the best thing for me has been that Ronald and I have gotten a chance to hang out and talk a lot since then, and actually get to know each other and understand that we went through part of the experience together, even though I wasn’t there with him. So it’s been fun going from the feeling of knowing him really well, to actually getting to know him much better.

Well, he seems to be enjoying the post-show glow and fame that has come his way. I do wonder where that’s going to lead for him and if he’s going to try to stay in show business or not.

I wonder too. But I think Ronald has a really good head on his shoulders. I think that’s why we picked him for the show. And I think he’s someone who makes good decisions. So I think whatever he feels is the right thing to do, he’ll be OK.

What did you want the emotional takeaway for viewers to be from the show, which is so funny throughout, but does get kind of deep by the end?

First of all, I am very proud of the fact that people are enjoying it and people are enjoying the comedy in it. I’m happy that we get some hard comedy in there, some big jokes, and that it’s a show that you can watch and actually laugh out loud. But I think the bigger thing is, I did not know if people would like the show or respond to it, because we were trying to show someone nice doing the right thing. And I didn’t know if it would be too soft. I didn’t know if that would sacrifice the comedy. I didn’t know if that's what people wanted to see. And it’s been really nice to see people respond to it in a positive way. I think Ronald, part of the reason we chose him is that he just displays a lot of decency to people. He gives people the benefit of the doubt. It’s nice to see that example and see that people like that and respond to that. It’s a good reminder to try to, as you’re going through life, give people the benefit of the doubt, show some decency. If everyone did that more and more, there’d probably be a little less divisiveness going on. I hope that’s part of why people respond to it. Because I certainly am happy that that’s in the show.

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Listen to the episode now and subscribe to The Last Laugh on Apple Podcasts, Spotify, Google, Stitcher, Amazon Music, or wherever you get your podcasts, and be the first to hear new episodes when they are released every Tuesday.

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