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VOICE OVER: Jennifer Silverman WRITTEN BY: Andy Hammersmith
Late night games never go according to plan. Welcome to MsMojo, and today we're counting down our picks for the most spectacular mistakes and/or entertaining mishaps during games played on late night talk shows. Our countdown includes risqué Pictionary, knowing Selena Gomez, blind taste test, and more!

#10: Guessing Secret Ingredients
“The Tonight Show Starring Jimmy Fallon” (2014-)


You might be a world-famous chef, but that doesn’t make you a professional at playing “Secret Ingredient.” “The Tonight Show” staff throws Gordon Ramsay and his fellow contestants for a loop with these insane dishes. Not only are the answers strange, the players are quickly stumped by almost everything. Ramsay’s culinary skills do produce partial credit for one question, but that doesn’t make up for his other misses. It’s unclear if anybody really wants to play this game either. We can’t blame them when they have to try to eat crickets in a chocolate cake. The whole thing feels like one massive fail, with the celebrity chef barely making it out alive.

#9: The Tallest Mountain
“The Late Late Show with James Corden” (2015-23)


The catch of this game is that you can lose money for yourself and others. James Corden runs through several contestants in “Know For Your Row,” witnessing a hot streak that stops with Isabella. The audience member already looks worried before the host even starts talking. She then makes the mistake of saying Mount Rushmore is the tallest mountain in the world. With her neighbors wincing, she takes her seat with instant regret. This mishap shows that you should always think carefully before answering. Along with embarrassing herself, she also prevents her row from winning.

#8: Blind Taste Test
“Jimmy Kimmel Live!” (2003-)


When Gordon Ramsay stops by “Jimmy Kimmel Live!,” he tests the host’s ability to decipher food blindfolded. The simple items prove to be much tougher for the blindfolded presenter than anybody could have imagined. Kimmel literally seems to have trouble figuring out that he’s eating cheddar cheese! He easily agitates Ramsay with his humorous commentary as he struggles. The same problem occurs when he’s eating plain chicken, once again testing the chef’s patience. We’re not sure how we’d do in the same situation, but we hope it would be better than this.

#7: Knowing Selena Gomez
“Jimmy Kimmel Live!” (2003-)


How well does this pop star know herself? According to this game, not as much as we might think. She faces off against Ashley during this trivia game. With a few exceptions, the superfan gives Selena Gomez a run for her money. Several obscure questions are a breeze for the contestant as she surprises the singer. Gomez tries to fight back, but ultimately she loses to one of her biggest fans. She appears to be embarrassed and even somewhat humbled by the extent of Ashley’s knowledge. All the while, she’s still a good sport about not winning.

#6: Risqué Pictionary
“The Tonight Show Starring Jimmy Fallon” (2014-)


You never know what will happen during “Pictionary,” including what the contestants will put on paper. In this segment, Catherine O’Hara tries to draw the “Star Wars” villain Darth Vader with mixed results. The comedian’s funny and unexpected pictures confuse Shailene Woodley. They also prompt the likes of Jimmy Fallon to point out their risqué nature. O’Hara tries to explain herself, but it’s too late as the images speak for themselves. Woodley is unable to guess, but at least we get a hilarious moment out of it. You be the judge of whether or not that looks like a gun.

#5: Charades with Charles Barkley
“The Tonight Show Starring Jimmy Fallon” (2014-)


Here, Jimmy Fallon pairs up with a not-so-amazing player on a “Tonight Show” game. Indeed, NBA veteran Charles Barkley can’t help the host in a major fail. For “Teenage Mutant Ninja Turtles,” Fallon tries to show off his best martial arts moves. Barkley proudly guesses “Karate Kid” in a hilariously incorrect response. Both players seem out of sync, infusing this segment with plenty of comedic friction. The lack of chemistry also translates to the second round, with the athlete trying to act out a Vanilla Ice song. In a funny outburst, Fallon calls his teammate out for not giving him good clues.

#4: Nathan Lane vs. Jimmy Fallon
“The Tonight Show Starring Jimmy Fallon” (2014-)


Nathan Lane and Jimmy Fallon are one prime example of two personalities clashing. Thankfully for those watching, this creates a hilarious rapport between them. Their first round of Pyramid ends up being a catastrophe, as Lane doesn’t get anything right. This disaster creates a more combative relationship between the teammates, with “The Birdcage” star going on a funny rant. As badly as they start off, we do love the witty back-and-forth banter that ensues. Even though they prosper in the second round, they still lose the overall game, running out of luck. They clearly need to reconsider their tactics for next time.

#3: Martin Short Explains a Podcast
“The Tonight Show Starring Jimmy Fallon” (2014-)


Even though Steve Martin and Martin Short might be friends, they aren’t exactly the best “Password” players. They face off against Jimmy Fallon and Margaret Qualley with constant banter to keep things light. When Short tries to give clues for the word “podcast,” he runs into several hilarious problems. He defies the rules of the game in order to try to help his teammate. This all culminates in Short saying the word, a memorable mistake that sabotages his team’s chances. The entire moment highlights the two legends and their ability to improvise through the pain.

#2: Taylor Swift Doesn’t Know Her Song
“The Tonight Show Starring Jimmy Fallon” (2014-)


In this segment, “The Tonight Show” host battles Taylor Swift in a “Name That Song Challenge.” The two keep things fun and competitive with a few surprises along the way. In the final question though, they have to guess “Shake It Off” – you know, the Taylor Swift song? Amazingly, Swift doesn’t seem to know as Jimmy Fallon swoops in to answer. Embarrassment washes over the singer, setting Fallon up to celebrate his win even more. It’s especially funny to see her completely miss the iconic drum opening. It’s an unforgettable flub, but it’s nice to see that the pop star is also human.

#1: Neil Diamond Loves Salad
“The Tonight Show Starring Jimmy Fallon” (2014-)


Time and time again, Jimmy Fallon proves that he’s super competitive. This game of “Password,” where Neil Diamond is his partner, pushes him to the limit. When Fallon sets Diamond up for a win, the latter fumbles with a priceless response. This causes the segment to break down and the audience to laugh. Then, when Diamond is giving the clues later on, we’re treated to a humorous callback from Fallon about the previous blunder. Everyone’s reactions and the comedian’s comedic timing turn this fail into an iconic one. It also makes us want to reconsider our own “Password” strategies.

Did we forget another hilarious fail? Let us know in the comments below.

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