Jimmy Fallon Shares Hilarious #VacationFail Segment for Memorial Day


| LAST UPDATE 06/02/2021

By Kayla Black
#worstroadtripever tweet segment fallon
Jerod Harris via Getty Images

While the Memorial Day weekend brought the opportunity for fun in the sun or even a quick getaway, some of us weren't as lucky. The Tonight Show revisited some #WorstRoadTripEver stories from over the years, and it couldn't have been better timing. Those of us who didn't get to lay on the beach during this holiday can find solace in these hilarious vacation fails.

#vacationfail jimmy fallon tweets
Frazer Harrison via Getty Images

After eating disgusting cupcakes with Sofia Vergara, these #VacationFail stories probably felt like a walk in the park for the television star. The tweets brought laughs to the crowd as Jimmy chuckled his way through them. Fallon got started with the tale as old as time: A dad misusing technology. @Kallie_fornia shared the hilarious mishap, where her old man was actually in selfie mode instead of capturing their vacation moments. And following the trend of classic fatherly moves, @Stacynovels tweeted about another pop's attempt at humor. "My friend has a prosthetic leg. As a kid, her dad would run out of the ocean with it, screaming "Shark attack!" "Not cool," The Tonight Show host chuckled, adding, "Yeah, it might be cool."

The next #VacationFail tweet put a hilarious twist on the dangers of sleeping in the woods. @Cheermomma84 recalled one trip where her family's wilderness skills were put to the test... Almost. "My dad and brother left us in the tent to investigate because they heard a bear. Turns out it was just my mom snoring," she wrote. The next mom-fail involved @Cuttsmarissa's parents' Baywatch moment. The Twitter user's mom misinterpreted her dad's distressed waves for help as a friendly gesture from the waters. Yikes!

Another one of the tweets selected for The Tonight Show left us feeling... A little disturbed. @Moniefry shared a picture of a piece of art that was hanging in a vacation rental home from a past holiday. "We had to hit it in a closet because it scared us all," she wrote. We can't blame her; even Jimmy and the show's announcer, Steve Higgins, struggled to understand the many layers of the unique painting. Take a look for yourself.

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Jimmy Fallon Memorial Day
Youtube via The Tonight Show Starring Jimmy Fallon

Safe to say, these #VacationFail tweets have served as some pretty hilarious conversation starters over the years. And lucky for us, the #WorstRoadTripEver survivors decided to share them with The Tonight Show. Jimmy Fallon delivered major laughs with his show's segment. And even provided some useful lessons for future vacation-goers. Remember to watch out for bears... Or snoring moms!