Welcome to the first-ever Challenge USA edition of Winners & Losers! We’re here with a whole bunch of people I’ve never seen before in my life. And maybe I’ve never seen them, but they’ve never seen The Challenge. They’re in for a bumpy ride, that’s for sure. Inside this edition: Voldemort speaks, Shannon does a push-up, we learn that the students at whatever high school James went to are super privileged, and much much more…
Loser: Jon Brennan
It took from March 7th 2005 when Jon Brennan wore his cowboy hat to the Inferno 2 house all the way up until May 11th 2022 when Jordan showed up for All-Stars 3 looking like the way someone who lives and works in LA would think a cowboy dresses for us to get somebody sporting the ten gallon on The Challenge….
And now we get another one?! Back to back?! What are we? Jonna?
I’m not saying that dude needs a new look or anything, but he just needs to know it’s beginning to get a little played out. That Italian restaurant’s not as special when your date finds out you bring all the girls there. Knowhatimean?
Loser: Guessing Games
Winner: Conniving Babies
“Hey, you. Other baby over there. I’ll trade you this probiotic and my window seat for your pillow.”
Fuck. Another cowboy?! We’re two minutes into this and the whole thing is officially played out. Young Thug should have never released Family Don’t Matter. It ruined everything. Shout out to Jon Brennan The Realest.
I can’t promise that’s the last time I’m gonna do that throughout this season, but I’m going to try my hardest. I swear to Jon Brennan.
Winner: Challenge Bullshit
Most of the time, when you break up with someone, and you’re past the grey area stage where you still hook up and fight all the time, the two of you just go your separate ways. Maybe you run into each other at a function of some sort, but otherwise, you’re done.
But welcome to The Challenge. Where jumping off the side of buildings and drinking cow testicle smoothies with your ex is just about as normal as taking a morning dump. In fact, you’ll probably take morning dumps right after one another.
Eventually, Cashay, if this show keeps happening, you’ll be exes with most of the cast. So don’t worry too much about this one.
Winner: Blatant Corporate Synergy
Keep gettin them checks Teej.
Loser: A Large Room Full Of Bunk Beds
This sleeping arrangement can go to hell.
Winner: Selling Your Soul
That’s right. You’re officially a human Under Armor billboard. Shout out to Steph Curry.
Loser: Suspending Disbelief A Bit Too Far
No. No way. No chance.
Loser: Breakup Tattoos
I mean, I get the impulse. But Jeez Louise just put a blonde streak in your hair or get bangs or something.
Over/Under five years until she ragrets getting that…I’ll bet the under.
Winner: Cleaning Up After Yourself
Big shout out to the handful of people who already did their own dishes in the middle of a party.
It’s not something I would do, because I’m, ya know, at a party. But in a communal living situation, every little bit counts.
Loser: Arresting Babies
I can’t possibly imagine what kind of crime that baby committed to get arrested. This world has lost its mind. Back when I was a baby, all my dad did when I got in trouble was tell me to get a job.
Is she seriously sitting on a bed crying about how stressful doing a push up is? Is that something I just watched? What the hell is going on? Where am I?
That’s right. He put it all together. He’s gonna mumble everything he says, cut off all the fingers other than the thumb on his left hand, and give himself a nickname rooted in the produce section.
I feel as though The Challenge is one of those things, like playoff basketball or having a kid, where no matter how hard you study and prepare for it, the only way to learn how to do it is by experiencing it.
I feel like the ones who are the most successful on this season will be the ones who understand that completely.
Loser: Me, Being Wrong, As Usual
I do know what you mean.
I take back what I said earlier. I’m all the way back in on Shannon. Push-us are for losers anyway. What? Do you think you’re better than gravity or something? Please. Grow up.
Loser: The Receptionist Working In That Building That Day
Imagine just trying to sift through paperwork because the freight elevator got double-booked that day and you need to move some things around so you don’t get screamed at again by the guy in Unit 406, and you’re already stressed cause this stupid TV show is filming here and the number of waivers you had to sign made you a little uncomfortable, and then some American girl is just twerking at you in the window for no reason.
No wonder the rest of the world hates us.
Loser: Naming A Pet After Yourself
So you’re tellin me this guy Leo has a cat named Leo?
Was the cat a rescue, and was already named Leo, so he got him because it was simpatico? Is his father named Leo, and he has no kids, so he figured that was the next best thing? Is the cat’s full name Leonardo? Is his full name Leonardo? Is the cat’s favorite Ninja Turtle also Leonardo? Is his favorite Ninja Turtle Leonardo? How do they feel, as a family, about Leonardo DiCaprio as an actor?
Lotta Q’s, not a ton of A’s. Story of my life.
Winner: Getting a “You Killed It” From Teej
I’ve set a lot of goals for myself in life. I’ve achieved some, missed on others, and still working towards plenty.
But there is one goal in life that I feel slipping away from me, and I’m starting to lose faith it’ll ever happen. And that’s to have TJ Lavin watch me do something and hit me with a “you killed it”.
There’s Nobel Prize winners and there are Olympians and both of those things are impressive, but there is no greater accomplishment one can achieve in life than to have TJ Lavin tell you that you killed it.
Shout out to Kyland and Azah. Their time here is a success, whether they win it all or not.
Winner: This Tyson Guy
What’s the ratio of Stanley Nickels to Challenge Bucks?
This Tyson cat is speaking my language so far. He’s got that way of talking where he’s simultaneously making fun of the thing he’s talking about while also taking it completely seriously. But if you ever laughed or pointed out the joke, he’d turn the joke around on you and ask why you’re laughing.
Wait, seriously? Does nobody drink on Survivor?
I mean, in theory, it makes total sense. You’re surviving and all that. But it’s still a TV show. You can’t like win a bottle of tequila? Is there no passing around a bottle of rum and telling stories around the campfire? What do they do with their time? Survive?
Winner: Love Island People
Shout out to them for being the only kids in class who understand the assignment.
Come on James, if you’re gonna hit somebody with the terrible news that they may in fact be going into an elimination that night, at least let them take a bit of their sandwich.
Shannon’s stressed out enough about the potential of a push-up contest, don’t deliver bad news on an empty stomach.
Winner: The Students At James’s High School
Those lockers are about three times as wide as the ones I had in high school. Jesus. Must be nice. Talk about coddled.
Loser: Being Cute and Walking Around
You’re being cute AND walking around?
I mean pick one or the other. There’s no easier way to be underestimated on The Challenge than to simultaneously be cute and walk around. Everyone knows that. If James knows reality TV like he claims he does, he should have warned Shannon as soon as they became partners.
I learned not to be cute and walk around very early in life. As soon as I uglied myself up and began crawling everywhere on my hands and knees, I immediately began getting picked for dodge-ball way sooner than before.
The two of them would be wise to adhere to those protocols. The underestimation will continue until they cease to be both cute and walk around.
I could listen to Shannon and James have conversations all day. That should just be the whole show. Lose the challenges. Lose the eliminations. Just show me James and Shannon talking about them.
Loser: TJ’s Stylist
What in the world? That ain’t it.
Winner: Losing An Eyelash On TV
Azah, don’t even stress. The last person I saw lose an eyelash on reality television was Rachel when Clayton the Bachelor broke up with her for the second time in 36 hours. And now she’s The Bachelorette! Or one of them at least.
So it’s only a matter of time before Azah meets 30 brand new single men and begins her journey to find love.
Oh perfect. How cool. Math.
Winner: The Challenge Gods
I know I say it a lot, but this group of people just got their first mouthful taste of Challenge Bullshit.
You wanna make The Challenge Gods laugh? Tell them your plans.
Thanks for reading! See ya in a few days for Winners and Losers for Episode 2! And, as always, Happy Challenge Watching!!!