When I read that the Internet Archive had released more than 2,000 MS-DOS games on their site, I surrendered to the retro-fever, hurrying over to click on and sample as many as possible, like Augustus Gloop in the Chocolate Room.
The Oregon Trail, however, was the one that I took my time with:
Look around at what?
It's a game that was dependent on the choices of 12-year-olds and willing to punish those same 12-year-olds with disease, despair, and death (in the game) when they chose poorly.
I hadn't played it since eighth grade computer science class. At the time I didn't regard the simulated pioneer crawl toward the West as anything more than a time-waster, but after two decades of playing and being both dazzled and frustrated by increasingly complex RPGs and console games like Fallout and Grand Theft Auto, the simplicity of The Oregon Trail has a certain appeal. And since nothing numbs the pain of rapidly aging out of pop culture relevancy in your 30s like trying to re-create a moment from your youth, I decided to take on the trail once more while keeping a semi-detailed (and mildly fictionalized) diary of my progress. Here's what I learned.
Creating the Characters
I open the game and make my first decision: hell and no, I do not wish to learn about the actual trail.
Don't be weird.
As the group leader, I go first. I call myself Jayson, adding the Y because I've always wanted my name to be spelled like that. For my occupation, I choose "Banker from Boston" because I'm a doughy Northeastern Jew and "Banker" seems more fitting than "Illinois Farmer."
When selecting the rest of my team, I try to think like someone who is actually mounting a mission across the great expanse of the American frontier. Someone in need of useful people.
Dr. Butt: I choose a doctor because it's always good to have a medic on board, because dysentery. Her name is Butt because I have the mind of a child. Dr. Butt hails from Colorado, where she learned her trade from a medicine woman named Dr. Quinn. As you may have guessed, each of these characters is going to have a backstory, because it would be less fun for me if they didn't, and again, this really is all about me.
Spyder Bob: A slow-witted cow-wrangler from the Texas Territory with a gluten allergy and slight creep vibe who walks with a limp that was caused by a bull's kick to his knee a few years ago.
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He's actually pretty cool about it.
"Healed stupid," according to Spyder Bob. This is not an official diagnosis.
MacGyver: A handy local guy with amazing hair and tiny nipples who is NOT the character from the 1980s television show for legal reasons. He's also an ordained minister and a notary public, should we need such things on the trail.
Your Mom: A semi-reformed hooker with a heart of gold who simply wants to set herself up in a new town where she can start a new life away from all the old dick that she's come in contact with in Missouri. If that's too many "Your Mom" jokes for you, strap in tight, like my spirit animal Karen Carpenter used to sing, we've only just begun ... to make bad sex puns about Your Mom.
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She's kind of a douchebag anyway.
Together, I'm pretty sure that we read like The Avengers of the frontier days, and it's because of our collective amazingness that I decide to embrace danger and the steepest challenges during this mission.
Offered spring as a departure time frame, I instead choose July. Bring on the heat waves and the snowstorms during this possibly six-month journey -- we can take it.
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We almost certainly can't take it.
Before we take off, I am required to stock up on supplies at Matt's General Store. I like Matt, despite the smell. I'm glad that the big-box retailers aren't around to pave over his life's work and break-up his family. With that said, I'm super disappointed by the prices and the lack of selection. Matt doesn't even sell rubbers, or, as they were called back in olden times, woolen dick socks.
I have $1,600 to spend, just enough for supplies and a little whore-buyin' along the trail. It's a long trip, and Your Mom has only so much energy.
Here's what I do and don't buy at Matt's:
2,000 pounds of food: Even though only 1,000 is required. We plan on getting really fucking fat on this trip.
Can I buy insulin?
Sadly, there are no gluten-free options, so Spyder Bob is fucked.
No clothing: I've decided that we're nudists, which should give us a little bit of an intimidation factor while trading.
99 boxes of ammo: Roll up on us. I dare you.
No spare parts: We have MacGyver, who has an uncanny ability to fix things, much like a guy on a TV show with the same name, but IT ISN'T HIM.
Four yoke of oxen: I shouldn't have to explain why I need this.
With our wagon full of ballers and cheap goods, we set out to carve our names into the ass of America's untamed West like a prison tattoo made with a rusted paper clip that is almost certainly responsible for the spread of hep-C in the A block.
"Yankee Doodle" plays us off. It is July 1, 1848.