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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.

YouTube
RIP, probably.

The Oregon Trail, however, was the one that I took my time with:

Wikipedia
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.

Archive.org
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.

Digital Vision./Photodisc/Getty Images
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.

Christopher Robbins/Digital Vision/Getty Images
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.

We Embark!

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.

Henryk Sadura/iStock/Getty Images
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.

Thinkstock/Stockbyte/Getty Images
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.

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On the Trail

We are 102 miles to the next stop. We ride strong. Your Mom has a cough, so I give her something to suck on.

We reach the Kansas River Crossing in record time, though I'm not sure people kept records back then. I choose to get out of the wagon and look around. It's pretty fucking dull, to be honest. Put a titty bar in, a wing place, a laser tag arena -- something.

The group suffers its first real injury when Spyder Bob breaks his arm. I consult with Dr. Butt, but she says that I shouldn't shoot Spyder Bob because he's "very good with the livestock."

A man named Big Louie at Fort Kearney tells me about a stretch of land where I will see antelope and buffalo. He is a gentleman in a coonskin cap and skinny jeans. We embrace as we part. I linger in the cloud of his scent, and then I buy 50 more boxes of ammo. Let's fucking hunt.

It's somewhat hard to control the action on-screen in the hunting portion of the game, due to the lack of fluidity, but I said I wanted simplicity, so here I am. These limitations don't hamper me as I try to kill pixelated woodland creatures, though. I shoot a buck and paint my face with its blood -- the forest is mine, for I am its king.

MacGyver has developed dysentery, but he refuses to let Dr. Butt treat him -- apparently he believes that the disease can be cured by sucking on a sugar cube while a scorpion teases his nipples with its claw. He is a weird dude, and I want to adopt him as my brother. Also, Your Mom has exhaustion. Sorry about that.

A woman named Celinda Hines comes up to us at Chimney Rock and says something about Indians trying to swap fish for clothing in the area. Even though our wagon train has decided not to believe in clothing, I am still intrigued, but I want to know more. Are these lake-fresh fish, or have they been raised on a farm? And if so, are they antibiotic-free and organic? It matters.

We try to trade with one emigrant (their word, not mine). He asks if we have an extra wagon wheel, and MacGyver laughs and says, "We have a hula hoop, some quick-dry cement, duct tape, and me," before walking away. He's so pimp.

I look at the map. We are really far away from our goal and already a quarter of the way through our food. I am stressing out, but it seems like there is "inadequate grass" wherever I go, so I'm forced to ease my troubles by drinking some wine that MacGyver made out of some grape juice and I don't know what else. He's like Jesus with better hair.

I change our pace to strenuous. Some of you are thinking that that happened a long time ago.

The Next Stop

We pass Fort Laramie next, but while they have the best whores according to Zagat's Trail Guide, we are trying to make time, so I give the reigns to MacGyver and have sex with a sack of rice. It is, amazingly, less dry than Your Mom.

Ryan McVay/Photodisc/Getty Images
Your Mom's got more protein in her, though, if you know what I mean (semen).

We have our first fatality on Aug. 16. An ox dies from a perforated bowel. Though I suspect foul play (and Spyder Bob), we move on.

MacGyver breaks his arm a few days later, but he again refuses treatment, choosing instead to make a sling with a pair of stockings and a paper clip.

At the south pass, I take out the map again, since the GPS is worth shit in this game. Our choices are simple: go south and lose time by going to Fort Bridger for more supplies or attempt the Green River Crossing, save time, and get supplies later. I choose the latter option even though I've been out of pork rinds for a week and I'm becoming the very embodiment of those Snickers commercials where the guy acts like a total shit face to his friends because he's hungry. Ugh, I'm terrible.

At the river crossing, an Indian man talks to me about the gentrification of the trail -- gone is the abundant splendor of untouched nature; it has been replaced by fro-yo spots and hot-yoga studios. He doesn't seem to like white men. I can't blame him. Historically, we're the worst.

Digital Vision./Digital Vision/Getty Images
Especially this bastard.

I wait six days for the ferry and pay $5 to cross. Spyder Bob and Dr. Butt are laying in the back of the wagon with fevers, so I can't really try to ford a 20-foot deep river. Soon we will be at the next base, and we will get more supplies. Perhaps someone there will have woolen dick socks.

I reach Fort Hall and buy supplies. I replace the dead ox, which makes Spyder Bob smile. I also buy a few spare parts (without telling the prideful and amazing MacGyver) and a few sets of clothes, which disappoints the group, as we had all come to enjoy our dick-swinging lifestyle. With the cold months upon us, though, I really have no choice.

Leaving Fort Hall, Spyder Bob gets bit by a snake. Shortly thereafter, he dies. I knew going into this that I might be leading people to their demise, but as we sit in Fort Boise, two-thirds of the way to Oregon and our dream of opening a craft brewery, I realize that I had started to feel as though we were invulnerable. A notion that I fear I will be further disabused of as we head toward our next challenge -- the Blue Mountains (cue thunder clap).

We reach the Blue Mountains on the day before Halloween. There, the trail divides, presenting me with one of those choices that seems like it could define a lifetime. Fort Walla Walla offers a chance to rest again and get more supplies, but I'm so close to being finished that I say fuck it and head for The Dalles and the more direct route. My grief and fear turning me blind to the virtues of caution.

Once at The Dalles, I opt to ride the Columbia River. It's dangerous, but it'll be faster, and it honestly sounds a lot cooler than the prospect of taking a toll road.

Almost immediately, I crash the wagon into a rock thanks to my inability to handle the elementary keyboard controls. All hell breaks loose.

Dr. Butt and MacGyver immediately drown -- I cannot save them. Seven of my 8 oxen also die, and 1,225 of my bullets, 580 pounds of food, and all the clothes are lost, rendering me as naked as the day that I came into this world and the day that I foolishly set foot on this trail.

Clinging to life and catching my breath with only a dialog box to pause my journey down this widow-maker of a river, I look around to see what my empire has dwindled to: one ox, a few bullets, and Your Mom. It's not much, but if this is what the good lord has decided to give me to start my life in the new West, then so b- I HIT THE SPACEBAR AND, AS IF PULLED BY THE DEVIL'S OWN LASSO, I CRASH INTO ANOTHER ROCK!

I have lost more bullets and my last ox. But worse, despite her impressive ability to hold her breath, Your Mom has drowned. Again, the dialog box stands as the only thing keeping me alive and away from that deathly river, but I know that I must hit the spacebar and accept whatever fate has been assigned to me. Will I wash ashore, empty-pocketed and heart filled with grief? Will I live on to honor the memories of Spyder Bob, Dr. Butt, Your Mom, and MacGyver?

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Epilogue

In the end, the gods teased me once more with the possibility of good fortune and survival. I glided along the river, dodging rocks for a few moments, making steady progress as I allowed myself to wonder where the next camp was so that I might restock for the final leg of my journey. Then I hit the river bank while trying to steer clear of another rock. Ironic. In the end, I made it back to land, my body shivering nakedly on the grass, my blood seeping down into the soil like rain.

Was it only yesterday when MacGyver told us tales about something called a Stargate that had brought him to this time? I don't think I'll ever forget the time that Dr. Butt got drunk on blueberry wine and told us about the day that she nicked a man's artery on purpose just to know what it felt like to have the power of a god.

Even Spyder Bob springs to mind as it becomes harder and harder to breathe. He was a disgusting creature, but I'll be damned if the howling noises that he made while sexing those oxen didn't scare off the coyotes on more than one occasion.

I'll be damned ... probably and deservedly. Not just for my foolish choices as the leader of this broken voyage but for the depraved things that I did with Your Mom. Oh, the erotic adventures that I had with Your Mom.

I'll miss her as much as I'll miss the sunshine, the theater that was the night sky, and the blanket that was the wind. And as the blackness chases out the light and silence becomes the last thing that I hear, I acknowledge that, even as an adult, this game taught me a vital lesson: The Oregon Trail cannot be mastered; it takes cockiness as a challenge, and it is undefeated.

Game over, man. Game over.

For more things games are teaching us, check out 5 Ways Video Games Are Saving Mankind and 5 Real Skills Video Games Have Secretly Been Teaching Us.

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