Top 10 Cringiest Wheel of Fortune Fails
Top 10 Cringiest Wheel of Fortune Fails

Top 10 Cringiest Wheel of Fortune Fails

VOICE OVER: Rebecca Brayton WRITTEN BY: Owen Maxwell
No amount of vowels can make the cringiest Wheel of Fortune moments better. For this list, we'll be looking at all awkward instances from “Wheel” that hurt the most to watch. Our countdown includes boozing my shore excursion, fish love, Magic Jand, and more!

No amount of vowels can make these fails any better. Welcome to WatchMojo, and today we’ll be counting down our picks for the Top 10 Cringiest Wheel of Fortune Moments.

For this list, we’ll be looking at all awkward instances from “Wheel” that hurt the most to watch. We’re basing our choices on a mix of obvious answers, baffling decisions and pronunciations that just sound weird.

#10: Bridal & Gold Shower

To say this guess took the audience by surprise is an understatement. Contestant Melanie was one letter away from solving a puzzle in the same name category. To many, the answer would have been obvious. Unfortunately for Melanie, it was not. The correct answer was actually Bridal and Cold Shower. Interestingly enough, it turns out that a gold shower is actually a real thing. Also known as a golden shower, the term refers to a particular fetish that we don’t even want to begin explaining. Host Pat Sajak has heard his fair share of r-rated puzzle guesses, but this one left him dumbfounded.

#9: Boozing My Shore Excursion

After a long back and forth on a regular clue, Rachel had only two letters missing. As the question was “What are you doing,” the answer was supposed to be “Booking.” Rachel appeared to get too into the vacation theme of the puzzle, and went in a more . . . intoxicated direction. The mistake was brutal as it could have been the answer. But it was worse to watch since it gave her competitors only one possible solution. Plus, the fact that this was a prize puzzle only made her loss more cringe-inducing. Since “Wheel of Fortune” has stayed away from less PG answers like Rachel’s, the alcoholic choice played off like a bad Freudian slip.

#8: Three Mistakes

Kevin was constantly in the right position during each puzzle for his run on “Wheel of Fortune.” When he should’ve said “Elevated,” he dropped a sentence that made no sense instead. This honest slip-up gave his opponent the obvious answer they needed. Kevin sadly flopped on “Dancing,” even when the letters didn’t add up. But it was his third incorrect guess on a butterscotch treat that would cement the tragedy of Kevin’s game of near-misses. He gave all his puzzles away just when they were in reach, and worse, he always cleared up any alternate guesses. Together, this triple-shot added up to a run so bad that Pat Sajak had to joke about it.

#7: Fish Love

For a quick toss up, Edgar was faced with a puzzle that was supposed to say “Wish List.” But Edgar threw a curveball when he gave a more aquatic answer. Though the letters could have worked, this choice was so weird that Edgar realized his mistake instantly. And there’s no way Sajak wasn’t going to poke some fun at him either. Nonetheless, he made it to the final puzzle and won an extra 30,000 dollars. To top it off, the producers gave Edgar one final laugh when they threw “Fish Love” back on the board. Edgar left the producers with classic material by simply ignoring the common phrases the game usually featured.

#6: A Group of Pill-Pushers

“Wheel of Fortune” is a family-friendly show, though Joe seemed to forget that when he focused his guess on narcotics. Joe’s choice is so against the show’s prime-time restrictions that Pat Sajak immediately scolds him for it. It was more painful since Joe had just confirmed that the two P’s he would need weren’t there. His opponent hysterically messed up too, though admittedly to a less scandalous degree. And the added irony that the actual answer was about “Well-wishers,” was just too rich to ignore. At least Joe was embarrassed quickly enough to acknowledge his error.

#5: I Have the Wine by Johnny Cash

When Natasha put a J on the board, it was pretty clear that her musical clue was about Johnny Cash. The song was apparently less obvious, as she added drinks to the title instead. Natasha’s flub looked bad considering that she knew about Cash, but not one of his most famous tracks. Besides, the H’s and E’s needed were already out of play in the puzzle. Sadly, Natasha also slipped up during a jackpot spin, which would’ve earned her nine thousand dollars and essentially a win for the night. Natasha’s bizarre response made such a great parody title however, that fans have remade the song in her honor.

#4: Self-Potato

Lolita McAuley buzzed in for a toss up, and all she had to say was “self-portrait.” Her actual answer was much more starchy, as she created a wacky new sentence on the fly. Lolita was so evidently embarrassed that she apologized immediately. And she laughably joked about walking off the show to save face. “Self potato” was so unusual that Pat Sajak and the other contestants were still laughing as the puzzle wrapped up. McAuley later said that she knew the answer, but the adrenaline of buzzing in on a toss up caused her mind to blank. So while she lost the money, Lolita gave audiences an iconic “Wheel” fail.

#3: Venice...Paris...France

David and Keri had spelled out their prize puzzle and won, with Venice mentioned in the clue. So when Pat Sajak asked them what country their trip was to, it was weird to hear a city, let alone a French one. Though the crowd was still laughing, David followed up with a country… but still not the right one. The brain-lock looked so awkward that Keri worriedly asked if they still got the vacation. After the mounting comedy, it was satisfying to finally hear “Italy.” Plus it was just too perfect that Sajak quizzed the one couple who didn’t know about Venice.

#2: Magic Jand

Zach’s run on a college episode of “Wheel” got him to the final puzzle, where he guessed all the right letters. It was just enough to leave him unsure what his “Magic” item was however, so he went through the whole alphabet. Since the wrong sound was stuck in his brain, he managed to try “Magic Jand” of all things. It was unbearably difficult to swallow when he finally got wand, but the buzzer had already gone off. The pressure got the best of Zach, and the regret was all over his face. If only he’d started at the end of the alphabet instead.

Before we unveil our top pick, here are a few honorable mentions.

An Ugly Child

Superman and Spider Woman

Bell Phone Charter

Regis Philburn and Kelly Reepa

Popsicle Bike

#1: Mythological Hero Achilles

Julian laid out every letter on the board, and had set himself up with several thousand dollars. Sadly, he didn’t seem to know how to say “A-Kill-EASE” and read the word phonetically. Since he ruined the pronunciation, the rules stated that he was wrong. This technicality has been used so rarely, so it was just devastating that it happened to someone who already spelled out the answer. On top of all the money lost, Julian also missed out on a chance to play his million dollar wedge. And his opponent earned so little on winning in his place, that they had to bump her prize up to a thousand dollars. The lesson here was . . . definitely to learn your pronunciation.