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Oregon Fail 

When innocently playing Oregon Trail, when one of your party members manages to magically break their leg while calmly riding in a wagon. Other incidents include your wagon falling apart while crossing a river, firing wildly in circles while hunting and missing every target, or another party member instantly dying from some horrible disease.
1) Man, what the fuck? My entire wagon exploded like 3 feet from shore. I just Oregon Failed.

2) "you shot 18 animals for 12563 pounds of meat. However, you can only fit 12 more pounds into the wagon" "Wow, Oregon Fail."

3) Ok, Jess just died of dysentery for some reason. What an Oregon Fail.
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Oregon City 

A rather boring city where not much happens.
I don't know what the hell the other definitions are talking about with drug usage, mild poverty and whatnot, but I'm guessing it's coming from some idiot rivalry between high schoolers regarding West Linn Highschool and Oregon City High School.
It's pretty fucking retarded.
Some students at West Linn burnt down a tree that was a memorial to a dead high schooler and some OCHS students burnt the West Linn football field so it will be difficult to run in or some shit (BURNT, okay. Think about that) because of this bullshit.
Overall, nothing fucking happens in Oregon City. It's a small-ass territory with a moderate population middle class people where nothing fucking happens. Ever.

I WISH there was poverty here. Then at least shit would happen over here and I'd have an actual reputation to be proud of.

If there are a substantially higher number of drug usage in Oregon City (Oregon itself is a liberal state. I mean, come on) it's probably because there isn't shit to do here.

If you want to do something while you're living in Oregon City, 95% of the time you'll go outside of Oregon City to do it. The most exciting thing here is a grocery store.

If you are raised here chances are you'll move out of it when you get the chance.

There is however a community college over here that is surprisingly very good... If you ignore the fact that society doesn't give a shit about community college and gives it a bad rap.
John: I live in Oregon City and do not own a car.
Rickardo: That sucks. You must be bored as hell
John: ... Yep... My sense of entertainment has died over time. I wouldn't even care if I died. I'd just sort of pass it off like a pothead...
Rickardo: OH YEAH?! HOW ABOUT WE TEST THAT THEORY?
*grabs a pocket knife and stabs John in the arm*
John: Thanks Rick. That was the most interesting thing that's happened all year.
You're the best friend ever Rick.
Rickardo: Any time John. Any time.
Oregon City by Squiggy McGee December 4, 2010

Oregon Exorcism 

When you fuck a pregnant woman so hard she goes into labor
She wasn't due until January, but Steve gave her an Oregon exorcism
Oregon Exorcism by Spencer Ace August 26, 2019

oregon dong 

The largest possible dong a man could possess
Damn that man has an Oregon dong

oregon trailing 

the act of deficating on a said persons chest starting at the naval and directing upwards toward the chin region
have you ever been on the oregon trail for the purpose of oregon trailing?
oregon trailing by E-jackulator August 7, 2010

Oregon High-Five 

Cannabis-infused Oil Fisting (vaginal or anal)
-"Why do I love the Oregon High-Five? It's gluten free, it goes right into the bloodstream and you don't even have to smoke it..."
Oregon High-Five by Lunea Moonrize September 4, 2013

Oregon city high school 

a bunch of hoes and fuck boys HAHAHAHAHA
random girl : “what school do you go to?”
guy : “i go to Oregon city high school”

girl: “oh so u fucking 2728282 bitches rn?”