Funniest Challenge Moments

JuneBug29 · 2026-03-21

Thread with 31 posts about Funniest Challenge Moments. Topics: Leroy, Anytime, Also, That, Then. Part of the Vevmo community archive.

Behind the Screen: Funniest Challenge Moments

For over two decades, MTV's The Challenge has been the proving ground where reality TV's fiercest competitors come to cement their legacies. What started as a Real World/Road Rules spinoff has evolved into one of the most physically and mentally demanding competition series on television.

The franchise's expansion — with spinoffs in the USA, UK, Argentina, and Australia — speaks to a global appetite for the brand of cutthroat competition and alliance-driven gameplay that Vevmo's community has been tracking since 2007.

i was ******* rolling the first time they told the story (rivals 1. ) on the shit show of how paula and johnny pretended to be a married couple to get bumped to first class, and paula got drunk and fe...

— challenger21

— rideordie95

Thread Summary

Discussion thread about Funniest Challenge Moments with 30 replies from the Vevmo community.

Which moments (whether intentional or not) had you LOL-ing?

Mine

- The Time To Ride challenge in Inferno 2. Anytime sombody fell off I was cackling. But it was especially funny when Julie decided she was going to go the short route without telling her team and as Landon and team were screaming at her she kept saying, "the road to God is straight and narrow" and fell off two seconds after she started. That had me howling.

- Also when Julie got eliminated on Inferno 2 and did a curtsey before she exited and MTV added a sound effect.

- Pretty much anything Darrell said/did on 1st episode of Fresh Meat 2 ( I ain't boo boo the fool! and him peeping with the binoculars)

- On Exes 2 when Leroy said he wanted whoever was going in to be a surprise. Then he said surpise mother ******! I was dying. Also when he said he was gonna be standing over Jay everywhere he went after he won the dome.

- Fresh Meat 2 when Wes seriously put Mandi on his back and they fell off the first rope immediately

- When MTV flashed Jay and Jenna's twitter names as Jay was talking about how much crap they were going to get for quitting

- When Timmy was mimicking Aneesa

- When Nia was going of on Nany, everyone in the background face was hilarious. Theresa was giggling like a schoolgirl, TJ was trying to hide his smirk, Bananas was trying not to laugh..and Wes was just sitting there with the saddest look on his face mute because he knew he was about to go home. ROTFL.

30 Comments

challenger21#2

July 17, 2015 - 1:16am

i was ******* rolling the first time they told the story (rivals 1?) on the shit show of how paula and johnny pretended to be a married couple to get bumped to first class, and paula got drunk and fell asleep with her noise cancelling headphones on. and when she woke up she thought she was deaf and screamed. ohhhh my god. to this day it is still so funny to me

rideordie95#3

July 17, 2015 - 4:12pm

i was ******* rolling the first time they told the story (rivals 1?) on the shit show of how paula and johnny pretended to be a married couple to get bumped to first class, and paula got drunk and fell asleep with her noise cancelling headphones on. and when she woke up she thought she was deaf and screamed. ohhhh my god. to this day it is still so funny to me

*******. I remember that

anon3895345345345#4

July 17, 2015 - 4:17pm

"When Nia was going of on Nany, everyone in the background face was hilarious. Theresa was giggling like a schoolgirl, TJ was trying to hide his smirk, Bananas was trying not to laugh..and Wes was just sitting there with the saddest look on his face mute because he knew he was about to go home. ROTFL."

THIS HANDS DOWN is one of the funniest moments ever and I've lost count of how many times I've watced that scene. Theresa was hilarious. She was loving every second of Nia going off ***** her reaction was like "YES Nia get her ***!"

The Cutthroat STSHS scene of Katie kicking Emily's top bunk bed with her foot is also one of my favorite moments.

rideordie95#5

July 17, 2015 - 4:20pm

"When Nia was going of on Nany, everyone in the background face was hilarious. Theresa was giggling like a schoolgirl, TJ was trying to hide his smirk, Bananas was trying not to laugh..and Wes was just sitting there with the saddest look on his face mute because he knew he was about to go home. ROTFL."

THIS HANDS DOWN is one of the funniest moments ever and I've lost count of how many times I've watced that scene. Theresa was hilarious. She was loving every second of Nia going off ***** her reaction was like "YES Nia get her ***!"

Lmaooo I can't stop rewatching that scene as well. Especially Bananas face was priceless when Nia said that Nany was the champion of sucking ***** lol...

WESANDNANYFAN#6

July 17, 2015 - 4:27pm

i was ******* rolling the first time they told the story (rivals 1?) on the shit show of how paula and johnny pretended to be a married couple to get bumped to first class, and paula got drunk and fell asleep with her noise cancelling headphones on. and when she woke up she thought she was deaf and screamed. ohhhh my god. to this day it is still so funny to me

HAHA that was hilarious

WESANDNANYFAN#7

July 17, 2015 - 4:29pm

KennyMaria was a really funny moment for me. God I miss Kenny.

Aneesa imitating Shauvon was ******* hilarious.

Landon and MJ pretending to be a gay couple.

Kenny drawing everyone's parents

anon3895345345345#8

July 17, 2015 - 4:30pm

"When Nia was going of on Nany, everyone in the background face was hilarious. Theresa was giggling like a schoolgirl, TJ was trying to hide his smirk, Bananas was trying not to laugh..and Wes was just sitting there with the saddest look on his face mute because he knew he was about to go home. ROTFL."

THIS HANDS DOWN is one of the funniest moments ever and I've lost count of how many times I've watced that scene. Theresa was hilarious. She was loving every second of Nia going off ***** her reaction was like "YES Nia get her ***!"

Lmaooo I can't stop rewatching that scene as well. Especially Bananas face was priceless when Nia said that Nany was the champion of sucking ***** lol...

LMAO!!! He was so shocked!

The Ruins between Katie and Sarah will always be hilarious to me. I love how they both flipped each other off after receiving a point and Sarah said "THATS FOR YOU!" and Katie shouted "**** YOU FAT *****!"

anon3895345345345#9

July 17, 2015 - 4:31pm

KellyAnne at the Island reunion hahaha

WESANDNANYFAN#10

July 17, 2015 - 4:34pm

KellyAnne at the Island reunion hahaha

"Yeah I **** my friends too"

HAHA she owned that reunion

bluehatchet2#11

July 17, 2015 - 4:36pm

She was a trashy hot mess.

But I like trashy Wink

anon3895345345345#12

July 17, 2015 - 4:37pm

KellyAnne at the Island reunion hahaha

"Yeah I **** my friends too"

HAHA she owned that reunion

That reunion is one of my favorites. I'm watching it right now and I love how KellyAnne tells the host that she's dating someone that we know but she won't reveal who it is and Johnny says "WHAT'S THE OPPOSITE OF EAST?!" and Ryan is like "Wes!" and KellyAnne looks all pissed saying "REALLY? REALLY?" then the screen cuts to Johanna's face lmaooo

DarkFights#13

July 17, 2015 - 4:37pm

KellyAnne at the Island reunion hahaha

"Yeah I **** my friends too"

HAHA she owned that reunion

"Where are you getting these things from like in your head ?"

WESANDNANYFAN#14

July 17, 2015 - 4:39pm

KellyAnne at the Island reunion hahaha

"Yeah I **** my friends too"

HAHA she owned that reunion

"Where are you getting these things from like in your head ?"

"Was Dunbar really your friend, you just met him"

"You just met her too, you wacky *****"

anon3895345345345#15

July 17, 2015 - 4:41pm

KellyAnne at the Island reunion hahaha

"Yeah I **** my friends too"

HAHA she owned that reunion

"Where are you getting these things from like in your head ?"

"Was Dunbar really your friend, you just met him"

"You just met her too, you wacky *****"

"But she didn't **** me over like you ****** over your ******* friend Kenny! REALLY KENNY? SHUT THE **** UP! SHUT THE **** UP! SHUT THE **** UP!"

MCM#16

July 17, 2015 - 4:45pm

KellyAnne at the Island reunion hahaha

"Yeah I **** my friends too"

HAHA she owned that reunion

imallergic#17

July 17, 2015 - 4:47pm

Julie wanting to wrestle Coral, "I don't wrestle, I beat******* up"

Almost any time Katie is pissed

Casey's height freakout on FM

Diem screaming while dangling over the cliff, Evan thoroughly enjoying dropping her on the Duel 2, and almost all of the gold from that *** They Should've Shown

Trashelle literally making zero sense in her fight with Aneesa's stiff arm

anon23423234235#18

July 17, 2015 - 5:44pm

The fights on Battle of the Seasons. teehee. also Marie.

Marie: Sam, I would kill you... by the way

Zach: And then I'll kill your man so SHUT UP!!!!

Marie: And then I'll kill your girl! So how about that!! *Elbows Robb on the head.

WESANDNANYFAN#19

July 17, 2015 - 5:46pm

The fights on Battle of the Seasons. teehee. also Marie.

Marie: Sam, I would kill you... by the way

Zach: And then I'll kill your man so SHUT UP!!!!

Marie: And then I'll kill your girl! So how about that!! *Elbows Robb on the head.

Marie is everything

DarkFights#20

July 17, 2015 - 5:49pm

Marie: Dolphin trainer ! DOLPHIN TRAINER

Debut Album#21

July 17, 2015 - 5:56pm

KellyAnne at the Island reunion hahaha

LOL @ Derrick's face.

Randome note: Robin looks great as a brunette.

And Kellyanne just looked dumb at the reunion. I mean I like trashy messes as much as the next one but that just wasn't entertaining at all.

MCM#22

July 17, 2015 - 5:57pm

Cooke is my Queen.

Debut Album#23

July 17, 2015 - 5:57pm

But that Julie moment on the Inferno 2 was definetly was one of if not THE funniest thing that ever happened on the show in my mind.

anon333334#24

July 17, 2015 - 6:00pm

Coral's confessionals in general....."look around, *****! There's only 3 of us!" said in a way that only Coral could lmaooo

anon333334#25

July 17, 2015 - 6:07pm

Beth going to tell Robin what Jodi said about Mark lmaoo she just KNEW she was starting some shit. She looked at the camera a couple times, overexaggerated everything & had to hide her face from laughing when Mark/Robin were arguing on the bus.

"Jodi grabs me, & she's like BETH! I WAS DATING MARK LONG & WE ******!!!!!"

Debut Album#26

July 17, 2015 - 6:10pm

Beth going to tell Robin what Jodi said about Mark lmaoo she just KNEW she was starting some shit. She looked at the camera a couple times, overexaggerated everything & had to hide her face from laughing when Mark/Robin were arguing on the bus.

"Jodi grabs me, & she's like BETH! I WAS DATING MARK LONG & WE ******!!!!!"

This was all halrious too. Especially when she snuck at look at the camera. It was even more funny when Derrick pointed that out at the reunion.

anon333334#27

July 17, 2015 - 6:21pm

- Excluding her team (who were awful) the way everybody else basically treated Sam like Meg from Family Guy.

- Marie randomly telling J.D. to shut the **** up & then arguing with him.

- Katie finding some of the most random people at any given time to go batshit on (Sarah & Emily). I could only imagine the laughs had she been on Seasons & she explodes on somebody like Laura or Ashley K. lmaoooo

anon3895345345345#28

July 17, 2015 - 9:25pm

Beth going to tell Robin what Jodi said about Mark lmaoo she just KNEW she was starting some shit. She looked at the camera a couple times, overexaggerated everything & had to hide her face from laughing when Mark/Robin were arguing on the bus.

"Jodi grabs me, & she's like BETH! I WAS DATING MARK LONG & WE ******!!!!!"

LOL Beth was the funniest instigator ever!!! I love how she was like "I'm not trying to be an intentional shit starter at all, I SWEAR!" in her interviews hahah

bluehatchet2#29

July 17, 2015 - 9:27pm

Beth and Megan Hauserman stg man they are ledgendary blondes. Smart and devious. Love them. Theresa could have been the new Beth but she's preggers ;( Hopefully the new Beth will reign in Violetta or Jenny or maybe even Marie.

Challenge 17#30

July 18, 2015 - 10:57am

The twitter names was great but my favorite was after Nany lost you just hear Theresa yell out "great job Nany!" In a smug voice lol.
Casey in almost all ruins missions was hilarious to watch lol.

Challenge 17#31

July 18, 2015 - 10:57am

The twitter names was great but my favorite was after Nany lost you just hear Theresa yell out "great job Nany!" In a smug voice lol.
Casey in almost all ruins missions was hilarious to watch lol.

Behind the Screen: Funniest Challenge Moments

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