YouTube star’s creativity on display in video game parodies

I knew clever people who make an ample living on YouTube existed, but I’d never actually spoken to one of these seemingly mythical beings  until I was introduced by a mutual friend to Gwendolyn Pinkerton. 

Gwendolyn is a cast and crew member of Random Encounters, a hugely successful, kid-friendly series of musical parodies based on popular video games.  In the viewer-driven world of YouTube, she is basically a rock star.

Random Encounters has more than 2 million subscribers and their videos have been viewed as many as 105 million times. They’ve partnered with Disney Digital Network and IGN Entertainment. When the stars of the series go to conventions, they tend to get mobbed by fans and have to be accompanied by a security detail. 

The show was co-created by Gwendolyn’s husband, AJ, after a Sonic-themed musical parody video won the grand prize in an international competition hosted by Sega. Gwendolyn and AJ met on the set of the video series, where their mutual professional admiration for each other eventually blossomed into romance. Soon, they were working together full-time. 

Random Encounters has been going strong for eight years and has tackled ambitious parodies of games including Sonic the Hedgehog, Pokemon, Legend of Zelda, Dead Space, Angry Birds, Assassin’s Creed, Mass Effect, Tetris, Minecraft, Portal, Five Nights at Freddy’s, Friday the 13th: The Game, and My Little Pony: Friendship is Magic. 

Gwendolyn’s work on the show is integral, both in front of the camera and behind the scenes, whether singing and acting in the videos, creating props and costumes from scratch, researching video games and pop culture trends, or taking care of the legal aspect of the business. 

The YouTube star is refreshingly down to earth and was kind enough to give me a behind-the-scenes glimpse into what it takes to create a winning video series.  She also talked about what it’s like to film in your own “backyard,” the joy of gaming for research purposes, her love of fantasy and science fiction, her lifelong passion for writing, and the broad curiosity that motivates her versatile creativity. 

Gwendolyn Pinkerton, dressed as Mei on the set of “A Mei is in Danger,” a musical based on Overwatch.

You’re a cast member (and also work behind-the-scenes) on the popular video game parody/musical web series Random Encounters, which airs on YouTube. I knew there were people who actually make a career out of YouTube, but I’d never met one before. It seems like the coolest job ever. Is it?

I love it. In the last few months, I’ve gotten paid to sing and dance around a park, light a puppet on fire in my garage, and duct tape an enormous number of switches and knobs onto a cereal box to recreate a video game prop. It is absurd, and wonderful, and I work with some amazing people.

When I’m in the mood to complain, I can find the downsides. The hours are long. I need to purposefully define “off-hours,” because there are always things to do. If I’m not here to do my work, no one else is, so vacations are hard to come by. YouTube is such a new platform, that it can be hard to find good advice when we meet a problem.

But most days, I have more fun at work than is fair.

Gwendolyn, wearing Mei’s Yeti slippers from Overwatch under her dress on the morning of her wedding to Random Encounters co-creator AJ Pinkerton. Photo: Heidi Marie Photography.

Your husband, AJ Pinkerton, is co-creator of Random Encounters. How did you guys meet and how did you become involved with the show?

Meeting him and getting involved in Random Encounters is the same story: we had a mutual friend who gave AJ my name when he needed a large cast for a new project. We ended up on set for twelve hours together, which was plenty of time to be impressed by his dedication and his talent. He knows how to coax a good shot out of difficult situations, and it’s fun to watch him set it up. He’s very good at what he does.

He tells me that he was surprised at how easily I worked the long hours, how much fun I had, and how energetic I still was at the end of the day. Over the next few months he asked me to help with several more projects, and I got the chance to do more than just act in them. It was the opposite of learning too much and ruining a magician’s tricks — the more I saw, the more I wanted to be involved.

Half a year in, we were dating, and I was working with Random Encounters about once a week around my day job. When we got married, I dropped the day job, and haven’t had a single regret.

You do a lot of behind-the-scenes work on the series, but you’re also in front of the camera, playing characters and singing. Do you have a background in acting/singing? Is this something that comes easily to you?

I was involved in community theater all through my teens. I’ve always sung along with the radio. I never imagined I would be either singing or acting professionally, but here I am!

I wouldn’t say performing comes easily. Before and after a shoot, I’m aware of how untrained I am, but when I’m in the middle of it? I’m surrounded by some very talented people. I’ve had the chance to work with amazing actors, singers, cosplayers, musicians, and techs. They’re excited and having such fun with what they do, that I can let go and have fun, too. On set, we bounce off each other, trade ideas, and the videos become very collaborative. The people around me make it easy, and I’m so grateful to have people around who add so much to the project.

Another of your jobs is making and putting together costumes and building props (which includes things like a giant Piranha Plant puppet). Tell me more about what this work entails. It sounds like it involves a lot of improvising and creativity. 

Oh, definitely. I can get so jealous watching Game of Thrones or Lord of the Rings these days, knowing the incredible prop and costume facilities they had access to, while I’m running around like MacGyver trying to make a freeze ray out a tin can and twenty popsicle sticks!

The process always starts with an image from a video game, which I’m trying to recreate. Depending on how good the graphics are in the game, I could be starting with something hyper-realistic with clear details, or some 8-bit splashes of color that I need to design myself.

I’ll have a discussion with my husband about shooting requirements (like whether we need to able to throw the prop across a room, or whether someone needs to be able to run in the costume) and then come up with a basic construction plan. After that, it’s a couple hours in a craft store picking out the materials that will best match what’s in my head, and then a couple days at my desk doing some truly ridiculous crafting.

My favorite thing is watching the materials transform. Often, it starts out looking like I’ve raided a kindergartner’s craft closet, and at the end I’m holding something that looks like I pulled it out of the game. The Piranha Plant started out as a foam ball and brightly colored fabric. But when I put them together and sewed the teeth in, it was like it magically became something else.

Gwendolyn, test driving a re-creation of “First Prize” from Baldi’s Basics in Education and Learning. She built it from PVC pipes, styrofoam balls, a lot of paint, and a remote controlled car.

You also mentioned that you deal with the “legalese” surrounding the show. What does that involve?

Miles and miles of paperwork. We are our own small business, so there’s a lot of financial paperwork and other minutiae that I handle. Any written agreements that we may have with other artists or collaborators, I’ll organize. Any contracts that we have questions about, I’ll research. And then I file it all. It’s about as exciting as spreadsheets and forms can get, but it keeps the rest of the production running smoothly.

You told me you have a “broad curiosity for different entertainments, arts, and skills.” Do you think that’s why you’re so suited to the demands of Random Encounters?

I can’t imagine having this job without that curiosity, and also the willingness to throw myself into things I know nothing about. Yet.

This is a fast-paced vocation. Because we put out a new musical every month, I could be using a completely different set of skills from one week to the next. Being curious about every new thing that comes along helps. Already having success in a variety of skills before I stepped into this makes me confident that I can keep up and stay in this for a long time.

But if I was giving anyone advice, no matter their job, I would tell them to stay curious. I think it makes life better.

Gwendolyn, doing a costume test for the character Ralsei from Deltarune. She created the costume, including hat, scarf, and coat.

I’ve heard that Random Encounters has a big enough following that you need security when you appear at conventions. What’s it like to experience that much fan devotion?

Add it to the list of things I never expected. I laughed the first time a convention assigned us a security team. Security is for rock stars; I just make videos on the internet. And then, incredibly, they had to escort us through a crowd of enthusiastic, screaming fans. I thought that was just for rock stars, too.

I’ve had moments when it was uncomfortable — there’s nothing quite like having to tell a 6-foot man with tattoos across his knuckles that you need to use the bathroom so that he can escort you there, or like encountering a fan in the bathroom, but I meet people who have traveled a hundred miles or more to meet us, and people bouncing on their toes at the chance to give me a hug, and I’m just grateful. Their excitement is exactly what gives me the opportunity to have this job.

What’s your fan demographic like?

They’re mostly kids and teenagers who love video games and theater. They’re amazing — creative and excited and they’re very generous with us.

From left to right: Rebecca Gabor as D.Va, Nathan Morse as Reaper, Gwendolyn as Mei, and Dom Boyd as Lucio on the set of “A Mei is in Danger,” a musical based on Overwatch.

One of the reasons I’m excited to talk to you is that Random Encounters is produced in my hometown. I recognize many of the locations where the videos have been filmed. What’s it like to shoot in your own “backyard”?

My job is very weird, but this might be one of the weirdest parts.

For the one thing, when we go for fun, it sometimes turns into a location scouting mission. My husband and I will pause date night to poke into the back corner of a park or neighborhood, just to see if there’s enough room to film away from general traffic because we like the scenery. We went to the local theater a few weeks ago and started asking how much it would take to rent it out for a day. Even our “off-hours” don’t stay so “off.”

And sometimes, while filming, we end up in the parking lot of our local mall at midnight, hoping that we don’t look like trouble to that security truck that keeps circling back around. Or we sing and dance around a park wearing ears and tails, pausing to let the dog-walkers pass. Or we run down our own street throwing ink at each other, pretending to be squids. No one seems to mind us though (which might be stranger than if they did), and it makes for great stories later.

AJ and Gwendolyn on the set of “If I Was an Inkling,” a musical based on Splatoon 2/Super Smash Bros. Ultimate.

I’d like to know more about the making of the series. Can you tell me about some of the behind-the-scenes work that goes into planning for a video?

We do all the things that a big production company would do, but we do it all between three people: myself, my husband, and our business partner, Nate. We select a project, write an original song, lyrics, and script, all based on either a popular video game at the time or an old favorite. We select a cast, scout a location or construct a set, purchase props and costumes or build them ourselves, and schedule a shoot day. Because our time frame is usually very short, we do it all at once, and we all pick up each other’s slack as we can. It can look pretty chaotic from the outside. It can look chaotic from the inside too, but we get it figured out.

Gwendolyn as Mimikyu and AJ as Detective Pikachu on the set of “Detective Pikachu the Musical.” Gwendolyn made the Mimikyu costume.

What about the work that goes into actually shooting an episode?

We shoot each project on a single day, if we can, and it usually takes six to nine hours. Sometimes it takes twelve. We keep a small crew, with only two or three people outside the cast to operate camera, run playback and other tech, and keep an eye on the shooting script.

That day is what we spend most of our time working toward, and there’s an exciting hour at the beginning when we all get into costume and we feel like we’re 10 years old, about to go trick-or-treating. It stays fun the whole day, but the excitement does wear off.

It becomes a game of keeping your energy up, even as you have to repeat one action — two, three, or five times — getting the shot to line up perfectly. “That was great, let’s do it one more time,” gets said about once a minute throughout the day. It’s all more repetitive that people think.

When we’re done, we take everyone out for dinner, because they’ve earned it.

Gwendolyn, finishing Mei’s snow boots for “A Mei is in Danger.” The rest of the costume was purchased, but she made the boots.

And then what does post-production involve?

Post-production is a lot of sitting in front of a computer — editing the footage, mixing the final version of the music, animating special effects, and color-correcting. It’s a very busy time, but the house is quiet while it’s churning. The whole team puts on their headphones and buckles down.

Sometimes we eat a celebratory meal at the end of that, too, when the video is finally posted. Other times, we just sleep.

How long does it typically take to shoot a video? Do you do them one at a time or several at once?

From first pitch to posting the video online, usually three to four weeks. There’s one or two that have been done in under two weeks, and there’s a few ambitious projects that took four or five months.

We post one a month, and generally focus on one at a time. It’s hard to know what will be popular in the coming months, so we stay on our toes and stay flexible, rather than getting locked into multiple projects at once. Unless we’re working on one of those videos that’s going to take four months. Then we have to, and business gets a little crazy.

Right now? We’re juggling three.

From left to right: Adriana Figueroa as Natsuki, Katelyn Herbert as Sayori, Gwendolyn as Yuri, and OR3O as Monika on the set of “Just Monika,” based on Doki Doki Literature Club.

You and AJ also perform live at conventions and events. That sounds nerve-racking. Do you enjoy that?

It is nerve-racking, also my least favorite part of my job.

You don’t realize how comforting it is to be able to do multiple takes of a scene until you suddenly can’t in a live performance. If you mess up, you can’t fix it; you just move on and try not to feel bad about it. We get stressed knowing we’ve only got one shot, and it takes a lot of fun out of it for us. We’ve been phasing that out of what we offer to conventions these days and been happier for it.

Gwendolyn tries out her new Nintendo Switch, a gift from AJ.

Random Encounters has parodied dozens and dozens of games, from Sonic the Hedgehog, Pokemon and Legend of Zelda, to Mass Effect, Assassin’s Creed, and Portal, to Minecraft, Angry Birds and classic games like Tetris. So, of course, I have to ask you about your relationship to video games. Did you play them as a kid?

I played PC games as a kid. I couldn’t tell you how many hours I put into Age of Empires, Battle for Middle Earth, and Myst. I had four siblings, and I remember fighting for time to play on the family computer. Sometimes we just settled for all playing Oregon Trail together. Those are the kind of games that still make the most sense to me, but I’m slowly working my way into others.

AJ bought me my first console for our anniversary last year, and he’s been laughing at me while I discover his childhood games like they’re brand new. Pokemon is blowing my mind right now, just trying to keep track of which “types” are strong or weak against others. A part of me wishes that I had gotten into those types of games earlier, but I’m also enjoying feeling like a kid again.

You’ve said you’re “really grateful to be in a position where I’m not sure whether I’m playing (video games) for fun or research.” I’m sure that would make a lot of gamers jealous. Do you actually play games for research? 

Yes. And it’s great to be able to relax and work at the same time.

We try to play every game we cover before we make a musical about it. For AJ, it’s imperative, since he does almost all the writing, and it’s the fastest way to understand the characters, the storylines, and the tone of the game. I try to play as well, so that I can be as helpful as possible on set, and push the project in the right direction, but I’m a lot slower at them than he is.

Part of our research is also looking at what people are talking about around the game. I look for fan-favorite characters or plot points that most shocked or excited players. I look for lines that people are repeating and using outside the game.

It’s awesome that I get to play games and look up memes as part of my job.

Gwendolyn at a Nintendo Launch event for Let’s Go Pikachu and Let’s Go Eevee in Santa Monica.

What are some of your favorite current games?

Overwatch, Undertale, Let’s Go Eevee, and Diablo III. And if I wasn’t playing so many at once, I’d probably get through them faster.

I spend the most time in Overwatch. I need a lot more practice, but I like how you can play thirty different characters, with thirty different styles, so the game never gets old. I don’t think I’ll ever be good at the snipers, but a girl can dream.

Any classics you go back to again and again?

I suppose it depends on how you define classics.

I’ve been playing Guild Wars 2 for the last eight years and can’t seem to escape it. It’s a massive game; there always seems to be something new to unlock.

I can always waste an hour in Plants vs. Zombies as well. I don’t think you can go wrong with a couple rounds of a tower defense game.

You also love books, particularly fantasy and science fiction. What sparked your interest in these genres?

There were a few years where I only read books with horses on the cover. I don’t know why. I think it’s just one of those things that you do when you’re little. One book happened to also have battle magic, knights, and a talking cat, and was ten times as exciting as the fifty books I had already read about stable girls doing their homework. So, I switched to only reading books with magic in them. Another thing you do when you’re young.

I have broader taste now, but I still really like the way that fantasy and science fiction play with reality. I think all of them start with a question about how people would change if one or two things were different in the world. At the very least, that can be a fun adventure. At the most, it can open up some very real and dear conversations about what our own realities are and why.

What are some of your favorite titles?

The Kingkiller Chronicles by Patrick Rothfuss, which has stunning uses of language and character. The Twelve Houses by Sharon Shinn, which is a romp and an incredible story about prejudice and power. The Raven Cycle by Maggie Stiefvater, which is so many wonderful things, but for me is about holding onto optimism, believing that even when you know where something is going, you don’t know how it ends.

I don’t think a book exists that every person on the planet will enjoy, but I think these are as close as you can get.

I understand you’re currently reading George R.R. Martin’s A Clash of Kings. How’s that going?

Great! I like to watch the adaptations of books before I read them (I find it’s easier to enjoy them both as separate stories that way), so now that the show is over, I have jumped head-first into the series.

Sansa Stark has been my favorite for a long time, and I love that the books are giving me a longer look at her as she grows. I think the characters — despite my living in constant fear that they won’t survive — are what drives the story so well. Martin has an incredible talent for telling an epic with a wide scope and making it feel personal.

When it comes to fandoms, you’re also into Marvel movies. What are some of your favorite films and characters from the MCU?

Captain America: The Winter Soldier will probably always be my favorite film in the MCU, unless I’m ever allowed to include Logan in that list. I think they both tell more vulnerable superhero stories and it gives them a leg up on the competition.

I love Natasha/Black Widow in just about every movie, but she’s especially fun to watch caught off her guard and trying to figure out Captain America. I wish we had seen more of the two of them working off each other, but I’m happy to have gotten what we did.

Any other favorite fandoms?

I have dabbled in so many — Supernatural, Doctor Who, Gravity Falls, Star Wars, Star Trek, Harry Potter, The Hunger Games, The Lord of the Rings, Percy Jackson — but I end up talking about Stargate a lot when I get asked this kind of question.

The last of the Stargate shows ended in 2011, so I feel it’s fallen out of memory, but it’s a solid science fiction story that still manages to play with mythology and it has alien space vampires. It was funny, intelligent, and I’m a sucker for the dreadlocked alien, Ronan Dex, played Jason Momoa before most people knew who he was.

Stargate is also how I met most of my friends in college — including the one who would eventually introduce me to my husband — so I may be biased.

You started writing when you were very young, studied creative writing in college, and have a fiction blog. What first sparked your love of writing?

I have no idea. My parents told me that when I was a toddler I would “write” stories for them — page after page of scribbles — and then come to them and read my story aloud. Whatever I got out of it must have been good, because I’ve loved writing longer than I can remember.

As a kid, I was very impatient, and writing was one of the few things that I liked every step of, instead of just wishing I could hurry up and have the finished product. I think that made it relaxing for me and kept me at it year after year. But I also have a lot of unfinished books hanging around because I don’t feel a need to get to the ending.

Gwendolyn as Playtime on the set of “Baldi’s Field Trip the Musical,” based on Baldi’s Basics in Education and Learning.

Do you do any of the writing for Random Encounters? What about coming up with ideas for shorts?

Nate, AJ, and I all discuss ideas together when we’re choosing each project. After that, AJ is responsible for the bulk of the writing, but Nate and I can both point to ideas and a word or two that was ours. Nate also writes a side series all on his own. I mostly stick to writing my own things, and am happy I don’t have to split my attention more than I already do.

Do you do any other kind of writing or just write for yourself? Do you have any aspirations to be published?

I’ve wanted to be published since I turned 8 and realized that I could be published (before that, I hadn’t thought about the fact that someone actually wrote all those books on my shelf). I had to put it off for a while due to some unexpected things, but I’ve been working on a novel all year and I’m a little in love with it. Hopefully other people will be too when I finish it.

While I love my current job, and hope to continue in it for a long time, I think novelist would actually be “the coolest job ever.”

You studied classical philology in college and taught Latin for a while. Do you happen to use any of the skills you learned in the making of Random Encounters?

Earlier this year, I would have laughed at the idea. There aren’t a lot of uses for either Latin or Ancient Greek outside of academia and sciences, even if I think they’re amazing languages.

Last March, though, AJ needed a Latin chant for some video game cultists, and I was ready for it. I got to compose our chant, and also teach it to our little choir. As usual, this job drops opportunities in my lap that I never could have expected, and I wouldn’t have it any other way.

AJ and Gwendolyn at YouTube Space London.

Random Encounters has been around for eight years, which is pretty impressive. What do you think is the secret to its longevity and continued popularity?

This is the part where I’m supposed to say something profound. This is where I lay out an equation and tell you what I’ve learned. I still don’t know how we do what we do. Honestly, we had our best year ever in 2018, and we’re still trying to figure out how it happened. We got lucky.

But every time I say that, I remember talking about luck with one of my professors. She agreed that so many things in life do come down to luck. Opportunities come and go unpredictably, and there’s no good way to anticipate when they’ll cross your path. But you can work hard and make sure you’re ready when they do.

I think that readiness to seize opportunity is what keeps us successful.

And it doesn’t hurt that music never goes out of style.

Can you give us a hint as to what may be in store for the future of Random Encounters?

In the next few months, we’re going back to some old games that we’ve worked on before. It’s always a treat to get back into old costumes and see what comes next. We’re excited to add a little more to stories that deserve another chapter.

After that, your guess is as good as mine, but I’m sure it will keep me on my toes.



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