Hot on the Oregon Trail: An Interview with Jim Stewart Allen

Comedian Jim Stewart Allen has had a lifetime obsession with an iconic educational game. The Oregon Trail graced our elementary school computers and captured our open trail hearts, but for Jim however, it’s a part of his daily life. Lonely Arts Club interviews Jim Stewart Allen on creating the Oregon Trail documentary.

Hi Jim Stewart Allen, and welcome to the Lonely Arts Club! You’ve played thousands of hours, presented live demos, and have even been on the KGW8 news promoting this 1971 educational game. You are an official Oregon Trail expert. If you were to describe this game in one sentence, what would you say?

An intense mid 1800’s journey across a continent through the miracle of 80’s coding and graphics that looked as cool then as it does now!

When did you first start playing Oregon Trail as an adult? When did you realize it was “something larger” in addition to playing it for fun?

Ha! It hasn’t really had time to start back up again because I have never really not played it! From when I first got it on a scholastic book order in ‘97 until now it’s just been something I do (I’m 30!).

I guess I realized it’s larger impact while playing it at my Grandma’s in 3rd, 4th, 5th and 6th grades. My Grandma would watch me play and ask questions and engage with me about the game, and I will always remember how fun that was! When I play it for others at shows I try to recreate that magic of playing it at my grandma’s all those years ago.

What was the catalyst for wanting to make a documentary about the Oregon Trail? Is this your first time making a documentary? Was it what you thought it would be?

I knew I had to do something with this game! I started playing at least one simulation per day on twitch (my streak ended at 1 year 8 months 22 days in a row!) and I knew I had to do something even bigger after that. One of my best friend’s, Sam Han, has his own production company (Rudy Studios) and I mentioned that we should do a documentary about the Oregon Trail computer game a few years ago, and he said if “I was serious he was serious!” And here we are!

Image of Jim Stewart Allen, Bill Heinemann, co-creator of the original Oregon Trail game, and Sam Han, co-producer of the Oregon Trail documentary

What are some highlights or favorite moments about this documentary journey so far?

Oh my goodness, so many! I think being featured on Portland’s KGW8 promoting the documentary about the 1971 computer game on the evening news was pretty surreal! I got to play the game while creator Don Rawitsch and I ate bison burgers, that was pretty amazing. Seeing the original coding at creator Bill Heinemann’s house was also incredible as well. All of these are filmed and will be in the documentary.

What are some unique challenges presented when creating not only a documentary, but a documentary about a game from the 70s?

I think proving myself worthy of telling this story, specifically to Don Rawitsch was pretty difficult! He wanted to make sure whoever told it, was going to tell it right, and that’s fair. He trusts us now, but it took a very serious approach and careful communication to make that happen. I’m lucky to get to tell this story!

Jim Stewart Allen and co-creators Paul Dillenburger and Bill Heinemann, Image by Sam Han

What has been the reaction from the community so far? Anything surprising or unexpected?

I think one of the coolest things to feel is how excited people are! Even 2nd graders I sub for who didn’t necessarily grow up with the game come up to me and tell me that when my documentary comes out they are going to watch it 10 times and tell all their friends, or that they told their parents and they are super excited to watch it with them! There hasn’t been any sort of major media coverage of this so it has been humbling hearing all of the, “I told all my friends and we are all so excited to see it!” comments.

I was on Tinder and had a woman from Wenatchee ask if I was the one making the Oregon Trail doc. You are a random person on Tinder in Wenatchee! There is some sort of magic in the air!

What are top secret tips to playing Oregon Trail successfully to the end without dying of dysentery?

Please, please, please make sure to rest! Anytime someone gets sick, rest! Anytime your health goes below fair, rest! Rest, rest, rest, whenever rest is needed. Thank you, this has been my TED Talk!

What can people expect when they watch your film? What would you like the takeaways to be?

You are going to get a really cool story about three student teachers who made a game that forever changed the way people engage with history! And this story is going to be told by someone who is really excited to tell it!

Bill Heinemann showing Jim the original coding for the original game. Known as the “sacred scroll”, there is only one, written just in case they needed it again. Image by Sam Han

You’re filming a live performance for the documentary on July 25th. Tell us more about it!

It’s going to be July 25th at the Comedy Underground at 8:30! Native American comedian/activist Howie Echo-Hawk will be featuring, and then I will be playing a simulation of Oregon Trail on the projector while the audience makes decisions! This will all be filmed live for the upcoming documentary, do not miss it!

Want to see Jim Stewart Allen and the Oregon Trail in Action on July 25th? Get Tickets Here! 

Want to support The Oregon Trail Documentary? Donate to their Crowdfunding Campaign!

Jim Stewart Allen is a stand up who found his comedic groove and voice in Bellingham, Washington while getting his history degree at Western Washington University. He now performs all over the Pacific Northwest, delighting audiences with his excitement and enthusiasm both in his stand up, as well as his show, “Oregon Trail Live” in which he plays the popular educational computer game The Oregon Trail, on a projector screen while talking about it. Jim has been featured on the Oregon Lottery commercials, as well as played the The Oregon Trail on the evening news. He is currently creating a documentary about the game featuring the three original creators.

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