Recently, I had the opportunity to see The Oregon Trail. Not the game itself, but the play by Bekah Brunstetter. I’d never heard of the play until a friend of mine informed me that it was playing at a theater in our town. It only took reading a few sentences about the play to make me want to see it.

I never actually got to play the fabled Oregon Trail game, although I was a fan of the not-quite-as-popular Amazon Trail. Oregon wasn’t offered in my computer class back in schoolmaybe I missed the mark by just a few years. But as I grew older, I began to hear fondly nostalgic tales of experiencing the wonders of dying of dysenteryall from the safety of school computer rooms.

Even though I’d never played the game, the concept of the play had me intrigued. The play uses the game as a framing device for a story about a 13-year-old girl who plays it to escape from the horrors of adolescence and “battling an undefinable lifelong sadness she cannot name.”

Teenage girls? Video games? Depression? It almost sounded like someone wrote a play with my interests at heart. I’ve written before on Sidequest about my experiences with video games helping me through my own struggles with mental illness. I was really excited to see a play that explored these themes, especially since I don’t usually hear about plays that center around video games.

A photograph of a handheld Oregon Trail game. The screen asks players to input party member names. Party members include: Sanders, Alex, Rachel, Maurice, and Zed. Yes, "Zed" is a reference to Zardoz, which we had watched the night before. The Oregon Trail, MECC, Brøderbund, 1971.

Yes, “Zed” is a reference to Zardoz, which we had watched the night before.

The theater we went to was really charming. They were playing 8-bit covers of famous pop songs and had computers set up in the lobby where you could play The Oregon Trail as you waited for the stage to open. They even had a little handheld version of the game to play, which was nifty, because other people were hogging the computers. It was my first experience ever playing the game, and I didn’t get very far at all. I only got past the first river before my friend and I decided to head over into the stage to get good seats.

The play starts with Jane, a sullen middle schooler who’s waiting for her mom to pick her up after school. She decides to hunker down in the computer lab and play The Oregon Trail to pass the time. Off-stage, a disembodied Voice of the Game narrates the game’s text to Jane and the audience. Immediately, the Voice starts go off-script while presenting the game’s dialogue. For example, The Voice asks Jane the typical beginning question of whether she wants to begin in March, April, or May“when your bangs stick to your face no matter what, and you are disgusting.”

Jane names her party members after herself; her older sister, Mary Anne; and her crush, Billy, the airheaded jock. Shortly after “Now” Jane starts the game, we’re introduced to “Then” Jane, “Then” Mary Anne, and their father. The family is going to take the trek from Missouri to Oregon, and “Then” Jane isn’t happy about it. She’s still grieving her mother, and she can’t understand how her dad and sister can just leave the home where she grew up.

For the first half hour or so, the play jumps between this troubled 19th-century family and present-day Jane, who’s stuck in the computer lab, making the game decisions that affect them. We begin to see the parallels between “Now” Jane’s and “Then” Jane’s lives. They are both a little whiny and seem to be struggling with depression. They both have an over-achieving older sister who has plenty of well-intentioned, but ultimately annoying, advice. 

The first half of the play was my favorite. I could relate as I watched “Now” Jane wallow in her teen angst while playing the game, especially since that’s something I totally did at that age (only I was probably playing Neopets or The Sims when I was 13). Jane rocks out to a lot of 90s throwbacks that are especially fun, including “Glycerine” by Bush and Alanis Morissette’s “Hand in my Pocket.”

Everything started to lose momentum for me when the play abruptly skipped about ten years. There’s a transition scene where the Voice of the Game and the in-game characters start to interact with “Now” Jane, guiding her through the rest of adolescence. She’s presented with a series of in-game text decisions about her college options and other typical coming-of-age milestones. A particularly funny bit includes “Then” Jane holding up a tombstone that reads “Your Virginity.” The next thing we know, “Now” Jane is a college grad who’s lost her job and had to move in with her sister. And Jane’s depressed. A lot more depressed.

I was caught off guard by that, even though I had known that the play would continue into “Now” Jane’s young adulthood. But I had become attached to the awkward middle schooler playing The Oregon Trail and complaining about getting her first period. I wasn’t ready to see her suddenly in a dysfunctional pile on her sister’s couch.

“Now” Jane rediscovers The Oregon Trail and starts to play again. The story of “Then” Jane and her family picks up where we last saw themsomewhere in the middle of nowhere, trying to get to Oregon. Honestly, I was less than impressed with the latter half of the play. It becomes a mish-mash of scenes of “Now” Jane being depressed and her older sister yelling at her about it, with the occasional scene of “Then” Jane being depressed and her sister and dad yelling at her about it.

I realized that I wasn’t exactly enjoying watching a play about the woes of an underemployed college graduate fumbling toward adulthood, because that’s already my life. In the immortal words of Pee-wee Herman, “I don’t have to see it… I lived it.

I realized that I wasn’t exactly enjoying watching a play about the woes of an underemployed college graduate fumbling toward adulthood, because that’s already my life.

“Then” Jane’s story becomes a lot more grim as her family falls victim to one of The Oregon Trail’s deadliest pitfalls. (I’ll let you take a wild stab at what that is.) “Now” Jane gets to reconnect with Billy, her crush back from middle school. That path goes down a disturbingly dark route that heavily hints at rape or sexual assault, which left me wondering why that scene was included at all since it was never mentioned later and didn’t seem to add much to the story, except to make Jane even sadder.

The two Janes do eventually meet, but I found the scene to be a bit… underwhelming. Although “Then” Jane makes it to Oregon (yay!), none of “Now” Jane’s pressing issues are solved, except that she and her sister are less mad at each other, and they have a heart-to-heart about what it means to be sad even though you live a relatively privileged life.

At the end of the play, I had more questions than answers. I wasn’t really sure what I had just watched, or what message the play was trying to convey. My immediate thought was that the play would be stronger as a whole if they had focused on Jane’s middle school years, instead of catapulting halfway through into a story about quarter-life-crisis Millennial ennui. More than once, I found myself wishing that Jane would just go to therapy already.

There were a few points when the writing didn’t sit well with me. When adult Jane goes on a date with Billy, she begins, unprompted, to explain to him in flowery prose how depression feels for her. It felt stilted, and like it was trying too hard to elicit something from me. There were other bits of similar dialogue that felt forced, like when Mary Anne confronts Jane about lying on her couch and doing nothing. “I hate you,” she says. “You smell like Parmesan cheese.” It was meant to be a serious scene, but a joke was thrown in, but it wasn’t really… funny. Just kind of awkward.

I don’t see many plays live, so I’m not sure which is more to blame: the writing itself, or the acting. Maybe if I had heard the same lines delivered with a different energy, or even by different actors, they would have connected with me better. Brunstetter has written several plays before, and works as a writer on NBC’s This is Us, so it’s not like she’s an amateur or anything.

Although I have my criticisms of the play, I don’t want to act like it had nothing of value to bring to the table. The first half or even two-thirds of the play is fun, and I did enjoy watching the play overall, even if I was scratching my head near the end. There are some genuinely funny moments that worked well. And I do appreciate any story that shows video games in a positive light. Since most popular media portray video games as mindless escapism, it’s nice to see games shown as vehicles for self-reflection and growth. It was also refreshing to see a story about video games from a female perspective, when gaming is usually depicted as a male hobby.

Desperate and confused, she asks the Voice what she’s supposed to do with her life, and the Voice keeps saying just one thing: “Continue on the trail.”

One scene that stands out in my mind the most is near the end, when everything has started to go unbelievably bad for both “Now” and “Then” Jane. There’s a bit where “Now” Jane doesn’t want to keep playing The Oregon Trail, but the Voice of the Game commands her to. Desperate and confused, she asks the Voice what she’s supposed to do with her life, and the Voice keeps saying just one thing: “Continue on the trail.”

I know that for a lot of people, including myself, part of the comfort in video games is that they allow us to have control when we otherwise feel powerless in life. I think that The Oregon Trail play, although a flawed work, succeeded in exploring how games allow us to take control in a safe space, and help us feel like we’re moving forward even when we feel directionless or overwhelmed with real life.

Oregon Trail Gameplay screen. The image shows an 8-bit covered wagon and an ox, with a thief leaving the scene of the crime. The text reads, "A thief comes during the night and steals 5 oxen. Press SPACE BAR to continue." The Oregon Trail, MECC, Brøderbund, 1971.

The Oregon Trail gameplay screen.