Podcast Summary

How to Be Anything – Episode 3: How to Be a Dungeons & Dragons Lorekeeper

Podcast by: Anything & Everything Podcasts
Host: Emily McCreary
Guest: Sky Smith (Lorekeeper/Story Editor, Dimension 20)
Date: July 23, 2025

Episode Overview

This episode profiles Sky Smith, the "Lorekeeper" for the hit actual-play Dungeons & Dragons web series Dimension 20 on Dropout TV. Host Emily McCreary explores the unique, niche role that Sky has essentially invented for themselves: tracking, organizing, and consulting on every tiny detail of a sprawling, improvised fantasy world, all while contributing to collaborative storytelling behind the scenes. The discussion dives into how Sky landed such an unusual job, what the work really entails, and what they've learned from living in the world of collaborative fiction.

Key Discussion Points & Insights

What Is Dungeons & Dragons, and Who Is a Lorekeeper?

• [01:19] Sky explains D&D as collaborative, imagination-driven storytelling:

  “It’s like a board game, but the board doesn’t come with it ... One person at the table is playing all the rest of the characters and the world and everything else. And that person is probably the person that introduced everyone else to D&D, because that person is the one who’s crazy at the table. Which I can say, because that’s me.” (Sky, 01:19)

• [01:57] “That would be the Dungeon Master.” (Sky)
• [02:37] Most games are played at home, but Dimension 20 is a TV show with a professional DM and Sky working as Lorekeeper, tracking everything that happens.
• [03:37] “Dimension 20 is an anthology series really ... 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.” (Sky, 03:37)

What Does a Lorekeeper Actually Do?

• [04:42] Sky on the uniqueness of their job:

  “My job is the title is Lorekeeper, which is crazy. That’s not a job that exists ... 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.” (Sky, 04:42)

• [06:12] Sky is the behind-the-scenes “Google” for the show:

  “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 ... If he says, the trees are purple in this city, the trees need to be purple. When we come back to the city later.” (Sky, 06:12)

• [06:51] Sky relies on massive, heavily customized spreadsheets (“Google Sheets on steroids”), sticky notes, legal pads, and sometimes an iPad to track everything.
• [07:52] Memorable moment showcasing Sky’s recall:

  “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 ... that season was six years ago ... I wish I knew why I know that answer.” (Sky, 07:52)

How Sky Became a Lorekeeper

• [08:46] Started as a production assistant (PA) in Hollywood, working odd jobs and activism to make ends meet.
• [09:16] Through connections in activism and previous jobs, Sky met people at Dropout over several years before landing a PA gig on Dimension 20.
• [10:05] Progressed from art department PA to Lorekeeper in 2023 as the show grew and needed more detailed story oversight.
• [10:12] Lorekeeper role evolved from note-taking to full creative involvement:

  “It’s not just 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 ... I get to be in that room and if I have opinions, I get to say them and they get taken into consideration.” (Sky, 10:12)

What Makes a Good Dungeon Master?

• [11:36]

  “A DM basically is the world of the story ... The DM comes up with all the side characters ... 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 also to keep track of the rules and the roles.” (Sky, 11:36)

• [12:24] Sky emphasizes the importance of trope, curiosity, and the twist—"telling stories that have not necessarily been told or to tell stories that have been told in a new way."

  “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?” (Sky, 13:00)

Creative Challenges: Tackling Steampunk & Sensitive Themes

• [13:19] Discussing the new season "Cloudward Ho":

  “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 ... it glamorizes sort of progress in a way that can be really problematic ... So we were like, what’s the honest truth to that story for us? And the answer is this season ... one of the most fun seasons, I think, that we’ve ever filmed.” (Sky, 13:19)

Sky’s Relationship with D&D

• [14:03] Didn’t grow up playing; started in late teens via friends:

  “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...” (Sky, 14:03)

• [14:46] Ironic note: Since working on the show, Sky has less time to actually play.

Putting on a Live D&D Show (Madison Square Garden!)

• [15:18] D20 sold out Madison Square Garden with a mostly improvised live show.
• [15:33] Sky describes the chaotic, collaborative process behind the scenes:

  “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 ... When they step out there at Madison Square Garden, we had full flames coming out WWE style ... Madison Square felt like nothing else any of us had ever done.” (Sky, 15:33)

• Other arena shows upcoming in Seattle and Vegas.

Favorite Dimension 20 Season & Characters

• [16:52] Choice: The Unsleeping City (premise: New York City, but magical)

  “It really is a love letter to the city. Brennan is from New York ... almost everyone of that season, lived in New York and met, I think, in New York. So it really was this massive love letter ... it was just so much fun. Like, it was like, oh, Sondheim is a bard, is a magical music creator ... well, yeah, kind of, like, what if that’s real?” (Sky, 16:52)

• [17:59] Memorable magical characters included a trans young man, a nurse whose magic comes from caring for NYC, a drunken Staten Island martial artist, a fae Broadway actress, a paladin firefighter, and a rat man who helped the city’s forgotten.

Notable Quotes & Memorable Moments

• On the job’s uniqueness:
  "It's not a job that I dreamed about having, but it is my dream job, if that makes sense." (Sky, 04:42)
• On being the show’s memory:
  "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." (Sky, 06:12)
• When Brennan asks for a six-year-old fact:
  "What was the name of that one cockroach from that season? ... Oh, Marty." (Sky, 07:52)
• On collaborating as a young, unconventional hire:
  "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." (Sky, 10:12)
• On the existential lesson of D&D and community:
  "Caring about people is a beautiful thing. And I think collaborative storytelling is a beautiful medium for, like, both teaching and learning that lesson." (Sky, 21:40)

Timestamps for Key Segments

• [01:19] What is Dungeons & Dragons? Table roles explained
• [04:42] Sky’s job title and tasks as Lorekeeper
• [06:12] The “Google” of Dimension 20
• [07:52] Sky’s legendary recall of obscure story details
• [08:46] How Sky landed in the world of D&D production
• [10:12] How the Lorekeeper role evolved
• [11:36] The art and craft of a great Dungeon Master
• [13:19] Navigating steampunk tropes in a new season
• [15:18] Behind the scenes of a sold-out Madison Square Garden D&D show
• [16:52] Overview of Sky’s favorite D20 season and characters
• [19:49] What this strange job has taught Sky about work, writing, and people

Lessons and Takeaways

• On Work & Identity: Careers are often built from confluences of skill, luck, and niche interests. Roles like "Lorekeeper" emerge because the creative world needs them—sometimes even before people realize it.
• On Creativity: Great fantasy storytelling cares about detail, respects the past, and looks for new twists on old tropes.
• On Community: Collaborative storytelling, whether at the table or behind the scenes, is an act of trust and care—one that makes stories and life richer.

Further Information

• Follow Sky and Dimension 20: Find more at howtobeanything.com.
• Watch the new Dimension 20 season (Cloudward Ho) free on YouTube.

This episode is a must-listen for anyone fascinated by offbeat careers, fantasy storytelling, or the serious artistry happening in the background of internet “hobby” TV. Sky Smith’s insights illuminate not just the mechanics of fantasy worldkeeping but what it means to build a unique role—and a life—around storytelling, memory, and community.