Sky Smith (1:58)

Really what it boils down to is it's collaborative storytelling, it's improvisation with friends, it's exploration of tropes. Like, my favorite thing about it in my games is how can we tell fun stories that mean something in a new way? And it's like a whole world. It's complete freedom. I constantly tell my younger brothers, I'm like, it's kind of like video games before there were video games. I think you guys would like it because they love a video game. And I personally think it's really great because it's what video games I think we're supposed to do for kids, which is exercise the imagination and excite them. And I'm like, you can do that with gaming.

Emily McCreery (2:37)

Dungeons and Dragons is almost exclusively played by people at home or at a gaming cafe with friends, as players invent their characters and plot in real time, guided by the dungeon master, often called a dm, who acts as a kind of director to the game. They must also roll dice to learn the outcomes of their decisions. So for instance, you want to fight another character or launch a burning arrow at a town and set it on fire, roll the dice to see if you succeed or fail. Sky is one of the only people in the world who gets paid to do what they do. Keep track of a long form game of D and D in detail. This is how to Be Anything, the podcast about people with unusual jobs. I'm Emily McCreery. Sky works on a TV show called Dimension 20, which airs on the streaming platform Dropout TV. On D20, there are six players and a dungeon master, typically played by Brennan Lee Mulligan, who created the show. And together they make up a story.

Sky Smith (3:37)

Dimension 20 is an anthology series really. At the end of the day, it is groups of people playing D and D and really telling stories through the medium of. I think we've grown and sort of changed who we are and like what the show is over time. But I would say these days, like, it really feels more like our primary action and goal is storytelling above gameplay. And the gameplay is like the medium that we tell the stories with, which is really fun. It's like a really fun. Especially for people who love a rule and love working around a constraint. It's kind of like Mad Libs. It's like you get to tell a story and it's going to be fun and it's going to be crazy. And part of the excitement is that there's an element of chance. You don't know what that story is going to be and that's what's fun about it.

Emily McCreery (4:31)

For any given game of D and D going on at someone's house, the dm, along with the players, keeps track of the story that's being told. But at Dimension 20, this is Sky's job.

Sky Smith (4:42)

My job is the title is Law Keeper, which is crazy. That's not a job that exists. At one point I do work for a company. So at one point someone said something to me about like, well, you know, according to market data. And I just had to be like, so politely and just so genuinely like, I am so curious what market we're looking at data from. I don't think there is a market. Yes. So my job title is Lorekeeper. We added a Slash story editor. Because it's not a real job title. And in this day and age, Lorekeeper does not play well on a resume if people don't know who you are. It's not a job that I dreamed about having, but it is my dream job, if that makes sense. Like, it really was sort of built around for me. I am building this job as I go. It is so niche to my skills and abilities that I'm like, I will never find another job that I can do like this. There is no other job that exists. Only Boost Mobile. Boost Mobile will give you a free year of service. Free year. When you buy a new 5G phone.

Brock Ciarlelli (5:42)

New 5G phone.

Sky Smith (5:43)

Enough.

Brock Ciarlelli (5:44)

But I'm your hype man. When you purchase an eligible device, you get $25 off every month for 12 months, with credits totaling one year of free service. Tax is extra for the device and service plan. Online only.

Emily McCreery (5:55)

Sky maintains a painstakingly detailed record of the story the players are inventing on the fly. They keep track in writing, but also mentally. And you won't see sky on camera. They're off screen, sitting in the video village with the director and producers meticulously taking notes in myriad form.

Sky Smith (6:12)

So my job is kind of to be the Google of the show. To be like, I'm writing it down. I'm remembering it so that you don't have to. The players need to be able to turn to me and be like, hey, I mentioned a certain snack that my character really liked last week and I forgot what it was. And I can be like, got it. I have it written down. And then on a bigger scale, also things about the world, because, you know, each of these players is creating their characters every week as the show goes on, but also our dungeon master is creating the whole world every week as we go on. And that is a lot of information. And it has to be consistent because that's how you keep a story feeling realistic. If he says, the trees are purple in this city, the trees need to be purple. When we come back to the city later, I have a crazy spreadsheet system going. So I have that open in front of me all the time. That's where a lot of it lives in. I like to refer to it as, like, Google sheets on steroids, because it really is. Like, what if we took Google Sheets and made it specifically for every spreadsheet nerd out there and made it crazy? But I also always have a pad of sticky notes on my desk. I usually have these, like, small legal pads that are just open on my desk. And sometimes I have like an iPad open at the end of the day, it's a TV show we're making. And so when we wrap on a day, the cast is meant to forget about it and go home. And that's the end of the day for them and for me. My job is to retain all of that so that they don't have to. It's crazy and impossible, and that's really delightful to me.

Emily McCreery (7:49)

In fact, Sky's recall is remarkable.

Sky Smith (7:52)

I think one of my favorite moments that happened in the last year is at one point I was at Madison Square Garden. Brennan looked at me and he was like, what was the name of that one cockroach from that season? And I just leaned back and I was like, oh, Marty. And he was like, that's right, Marty. And the cast was like, that season was six years ago. And I was like, yeah, I wish I knew why. I know that answer. I really do.

Emily McCreery (8:16)

Yep. D20 is so popular. They played a live show at Madison Square Garden earlier this year. But we'll get to that in a minute. The fact that sky knew the name of a cockroach is made even more impressive by the fact that they didn't even work on the show then. Sky was actually working as a production assistant in Los Angeles. PAs do a lot of the grunt work on a film or TV set, making coffees and answering phones, maybe a little bit of crowd control. If the production is filming in public, it's low paying contract work with no stability.

Sky Smith (8:46)

It's nearly impossible to survive being just a PA in Hollywood without any sort of higher connection. So I also worked in activism. I worked for a social ecological justice group. And between those two jobs, I ended up working enough to make some connections in the film industry, where I was able to sustain between the two of them.

Emily McCreery (9:11)

Sky worked at an improv theater in Los Feliz and later worked as a PA on a scripted show about D.

Sky Smith (9:16)

And D. And through that show, I actually met a couple of people who worked at Dropout, a couple of cast members that worked at Dropout. And through my activism work, I met someone else who worked at Dropout. And it took years. Honestly, like, every time I ran into people at Dropout, I was like, oh, they were very kind. They were very great to have on set. They would say, oh, if you're ever looking for a job, let me know. And I'd be like, I'm always. That's the film industry. You're always looking for a job. But, you know, people say that and they'll like, reach out and give your information, but at the end of the day, it's a crazy competitive industry. And so I never sort of expected anything to come of it. And then eventually I got a call being like, we need a PA on short notice. Are you free? Do you want a PA on the show? And I was like, yeah, absolutely. And it ended up being D20.

Emily McCreery (10:05)

Shortly, sky was moved to the art department as a PA and in 2023 was brought on as the Lorekeeper.

Sky Smith (10:12)

There was a script supervisor who was also titled as Lorekeeper before I ever came to the show. And she was there when I first started, and she set up a lot of the, like, post production processes that we have, because a lot of my job is like, tracking that information for when we go into the edit. And so she would take notes on set. I mean, she was incredible. She laid the groundwork for sure, and she really created the foundation that I started with when I stepped into the role. A big part of how it ended up in my hands and why it was given to me is because the show has grown so much. We have to change what the role of Lorekeeper is, to be a little more comprehensive, to not just be note taking, to have to do the creative, the writing, the recaps that I'm doing now. And I also get to do a little bit of creative consulting, which I love and is one of my favorite parts is when we're talking about the world and the story that we're building for a season. I get to be in that room and if I have opinions, I get to say them and they get taken into consideration, which I think is a huge blessing, Especially as someone who's, like, young and I didn't finish college, I'm so grateful to have a job at a place where people are still willing to see me as an equal or a peer and give me an opportunity to have a voice, especially because writing is my passion. It's what I want to do with my life.

Emily McCreery (11:33)

What does a DM do and what makes a good one?

Sky Smith (11:36)

A DM basically is the world of the story. So if D and D is collaborative storytelling, the DM comes up with the setting, the DM comes up with all of the side characters because each player is in control of their character. But for a world to feel real and diegetic, you have to have a shopkeeper, you have to have your brother, you have to have your parents. And so the DM's job is basically to create a world that feels realistic and that you can live in Diegetically in session, and also to keep track of the rules and the roles. I think what makes a good DM is someone that, first of all has a sense of story and trope, is curious about not just regurgitating stories that have already been told, but telling twists and new ones. One of the best parts, to me, about D and D and about collaborative storytelling is the opportunity to tell stories that have not necessarily been told or to tell stories that have been told in a new way. And so when we're creating a season, when we're creating characters, we do end up falling into tropes, for sure. There's no way around it, but just as much it's. What's the twist on it? Like, how do we, you know, like, oh, yes, they're enemies to lovers. But what makes it interesting, we've seen enemies to lovers before. What is unique about the story we're telling? Oh, they're enemies to lovers on a battlefield, and they're people made of candy. Maybe. Like, what is going to be the interesting thing about it?

Emily McCreery (13:10)

There's a new season of Dimension 20 out. It's called Cloudward Ho, and you can see the first episode on YouTube if you search for it there.

Sky Smith (13:19)

And it's sort of steampunky fantasy adventure. It was sort of our way of being, like, what are all the things about steampunk that we love? And what's a way to tell that story without all of the pitfalls of steampunk? Because there's a lot of, like, aspects of steampunk stories that often come with, like, really either glamorized colonization or dramatized colonization. And it sort of treads on a lot of indigenous stories, and it glamorizes sort of progress in a way that can be really problematic. And so we were like, what's the honest truth to that story for us? And the answer is this season, which was one of the most fun seasons, I think, that we've ever filmed.

Emily McCreery (14:01)

Did you grow up playing D and D?

Sky Smith (14:03)

I did not. I grew up exposed to it. I had a lot of friends that played. I dated some people who played. I never really, like, knew that side of him, but I guess my dad played when he was young. So genetically, there's something in there, but I sort of did not have an interest in playing it until I was in my late teens. And then when I did start playing it, there's something that happens when you're Type A and a little bit crazy where you get sort of pigeonholed into being the DM because It is a really crazy task to take on, and you have to love it in a certain way. So very quickly, I became the DM of my friends, and I used to go play at local game shops just because I was like, sometimes I don't want to be the dm. Sometimes I want to just play for a day. But funnily enough, I think I play less now that I work on the show than I ever did. Just because it's like, with what time. Like.

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Emily McCreery (15:18)

Like I said before, the show is so popular that Dimension 20 played Madison Square Garden in January of this year, and the show sold out. They do build some of the plot ahead of time, but it's a live show and almost entirely improvised.

Sky Smith (15:33)

So it starts with, like, Brennan and sometimes the cast, and they'll sync on something, and then he'll bring the beginnings of an idea to us and then to us being the creative team. So me and my boss, our series producer and our director and our art directors, and we'll sort of tease something out of it. It'll change a few times. It'll be different iterations. And then just over the weeks and until we get to the show, we, like, lock down different aspects of it until we feel good. But honestly, it really is crazy how much of it is up in the air up until they're out on that stage. It really is improv. And at the end of the day, that is our guiding. We try to plan some things so that we can do cool production effects, but at the end of the day, we have no idea what's going to happen. When they step out there at Madison Square Garden, we had full flames coming out WWE style. It was crazy, crazy. We have, like, Steadicam operators with the camera, like, chasing the players on stage when they, like, get up to, like, celebrate a role. Madison Square felt like nothing else any of us had ever done, and it's still crazy, like doing the big arenas. We have another one in Seattle and then one in Vegas later in the year. And, like, it's going to be crazy every time.

Emily McCreery (16:47)

Can you give me an overview of the plot of your favorite season?

Sky Smith (16:52)

I think my favorite season is probably the first dimension 20 season I ever watched, which was called the Unsleeping City. And basically the premise is, what if new York City was magic. What if it was the New York City we know and love, but also there's magic. And as someone who lived in New York City for a while and loves it, and a part of me is like, I will go back one day and live there. It really is a love letter to the city. Brennan is from New York, and a lot of our cast, almost everyone, if not everyone of that season, lived in New York and met, I think, in New York. So it really was this massive love letter to a really incredible city. And it was just so much fun. Like, it was like, oh, Sondheim is a bard, is a magical music creator. And it was like, well, yeah, kind of like, what if that's real? Because it would be, you know, like, Sondheim would be the one who's making magic with music. And I think it's just. There's just something so fun about taking reality and making it a little more magical.

Emily McCreery (17:55)

What kind of characters were people playing? Was someone playing Stephen Sondheim?

Sky Smith (17:59)

So the DM did bring in Stephen Sondheim, which was really crazy. But we had the cast of characters that time was a young man in his 20s. He was trans, a little bit of a mess, and very lovable. One of the fan favorite characters there was a New York City nurse who was like, the voice of the city. His magic came from being someone who cares about the city, from being a New Yorker and putting everyone else first. There was a monk, so, like, a martial arts fighter who was from Staten island and was frequently drunk and would, like, have a little coronita on the ferry. There was a Broadway actress who was actually a female fairy. She was fae, because. Yeah, that, you know, that makes sense. And, like, her whole thing was, like, she got her magic and her power from the adoration of fans on Broadway, which, as someone who was very present at stage doors in 2018, yeah, you get a lot of power from that. And then there was also, like, a New York City firefighter who, like, was a paladin and his oath was to protect the city type thing. And then a rat man who lived in the sewers and took care of the unhoused and the forgotten denizens of the city, including trolls and mice and all of the animals and all of the people who are discarded and forgotten, which was really beautiful at its core. Most stories are about the relationships and the bonds between people or people and things or people and places. And so I think my favorite parts of the stories that we tell has to do with the fact that our stories are Intentionally focused on the relationships because that's who is driving the story. It's a cast of players playing these characters that need to have a relationship in order to have a story.

Emily McCreery (19:49)

What has this job taught you about life? People writing, honestly, a lot.

Sky Smith (19:57)

To be completely transparent, I'm pretty young, and, like I said, I didn't finish college. It's my first real corporate job that I've really been able to hold. And so on, like, a very surface level, like, just learning how to be a professional. And I'm, like, really lucky to be at a company where they're willing to sort of let me make mistakes as I do so, because I think there's a lot of companies where they would not tolerate the amount of shenanigans that I have in my body at all times. And so, like, I am really grateful that I have the opportunity to learn how to switch, sort of get it together, be a professional, be an adult, and then, like, as a writer, I mean, I really have never been surrounded by better writers in my life. Like, it. It really is such a blessing to just even be in the room when these minds are like, well, what if we did this for story? And I think the other thing that it's really taught me is, like, how to work with people, how to tell stories with people in a way where, like, you can't be a pushover, and you don't have to be a pushover, but you do need to listen to people above all else. I think one of the greatest things that it's taught me is, like, you have to care about other people. Like, this industry is so cutthroat, and even, like, just this world that we live in now is so very centralized around, like, well, what about me? And I think working in a show where by nature it's collaborative has really, really been able to, like, solidify. For me, like, that is going to be the thing that I think kills us as a society is this knowledge of, like, well, what about me? It's like, no. What about community? What about the people that you care about? What. What is the worst thing that happens if you care about people at the expense of yourself? Inconvenience is a beautiful thing. Caring about people is a beautiful thing. And I think collaborative storytelling is a beautiful medium for, like, both teaching and learning that lesson.

Emily McCreery (21:51)

How to Be Anything is written by me, Emily McCrary. Lily I. Johnson is our producer and Kaden Boffman is our editor. Visual design by Nika Semovic Fisher at Labud. You can learn more about sky and about Dimension 20 on our substack howtobeanything.com and follow us on Instagram. How to Be Anything if there's a job you think we should feature, let us know@howtobenythingpodcastmail.com.

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We played best friends on the Middle.

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Each week we'll recap an episode with behind the scenes stories, guest interviews and what we think.

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