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The 10 Most Memorable Mismatches in "Amazing Race" History

Teeuwynn has been a game designer, author, and TV writer since her career began back in the '90s.

Memorable mismatches of the show.

Memorable mismatches of the show.

Amazing Race Detours and Roadblocks

The Amazing Race is a grueling CBS reality show that sends teams of two racers dashing about the globe, completing challenges of all kinds, in an attempt to be the first team to the last Pit Stop so host Phil Keoghan can declare them the winners of The Amazing Race and one million dollars.

Unfortunately for even the most promising teams, just one challenge weakness can bring them crashing down and out of the race. Sometimes teams go out on a Roadblock, where just one member of the team can attempt the challenge. Other times, a Detour or different challenge brings the team down.

Look below to see ten of the most memorable mismatches between racers and challenges on The Amazing Race.

1. Pick a Pearl

In this Detour option from Season 22, Episode 2, twin doctors Idrires & Jamil chose the Pick a Pearl Detour option. In this option, teams had to harvest pearls from open water about a half-mile offshore. Each team needed to find two red pearls among the white pearls.

Unfortunately for Idrires & Jamil, the two doctors were petrified of water. They froze, with neither one able to dive into the water. Idries later said, “It was petrifying. It was so deep and it’s just everywhere.” Jamil wanted to just take the six-hour penalty, but Idries convinced him to at least try.

Although the brothers eventually began retrieving one oyster at a time… very slowly… they continued to follow farther behind. Jamil eventually grew so exhausted that he had to call for help from rescue divers. After their inability to complete the Detour, the team was exhausted and never managed to recover, even losing to two teams who started the leg hours after the brothers.

Brothers Idreas and Jamil

Brothers Idreas and Jamil

2. Kafka Chaos

In Season 15, leg 11, the teams went to Prague, home of the writer Franz Kafka. The Roadblock thrust teams into a Kafla-esque nightmare of hundreds of ringing phones in an otherwise empty warehouse.

The teammate doing the Roadblock had to pick up and listen to the many, many phones searching for five different ones that each said a letter; “R, Z, A, F, and N.” If you anagram these they spell “Kafka.” Once the players found the five letters they had to fill out a form filled with nonsense questions followed by a chance to present their answers, in the right order, to the waiting Supervisor.

Dan of the brother team Sam & Dan agreed to work with Big Easy from the Globetrotters team, but when Dan got the result first he sprinted off without telling Big Easy the answer. The most Dan would say was the answer started with “F.” Big Easy was not happy.

Big Easy grew extremely frustrated as the hours went by. He ended up trying over 100 different answers -- more than he would have tried if he had gone logically through all possible solutions. Finally, Big Easy gave up, taking the four-hour penalty and ensuring that Big Easy & Flight Time were the next team eliminated from The Amazing Race.

Big Easy stuck in a Kafka-esque nightmare.

Big Easy stuck in a Kafka-esque nightmare.

3. Who’s Ready to Break Wind?

In St. Tropez on leg four of Season 30, former pro basketball players Cedric & Shawn were running behind after finishing last in the non-elimination leg the previous episode. This Roadblock required a teammate to maneuver a child-size dinghy out into the windy waters to two different buoys to pick up two halves of the next clue.

Although the pair made quick work of their Speed Bump of carrying and stacking boats, when it came to the Roadblock the team picked the 7’4” Cedric to take on the boating task. Unfortunately, the child-sized, plastic boat made it extremely difficult for Cedric to get into the boat without immediately swamping it.

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Cedric tried again and again, growing more exhausted all the time. Finally, he managed to scrunch down entirely in the boat, and with the water lapping at the very edges of the boat, he managed to complete the challenge. Unfortunately for Cedric & Shawn, the effort was too little too late.

Cedric capsizing the boat.

Cedric capsizing the boat.

4. Running with the Ballz

In The Amazing Race: All Stars, cowboy brothers Jet & Cord, took this Detour option where players had to get inside large, inflatable balls and roll through the streets of Spain looking to find words that made the phrase, “A matador never thinks about his own death.” To add just a bit more difficulty, players were attacked periodically by people dressed up in bull costumes who would smash into them and knock them around, disorienting them.

The cowboys took a long time to find the clues and put this message together. The delay caused them to slip in position and lose the race this leg, despite their previously strong showing.

5. Flo Freaks Out… and Freaks Out… And Freaks Out

Zach & Flo were actually the winners of The Amazing Race 3. The two were a potentially dating couple, although by the end of the race that potentially seemed to be gone from Zach’s mind. Flo spent the majority of the race whining, screaming, and complaining -- not just at Zach, but at the other racers as well. Flo’s ongoing meltdowns at the slightest sign of stress made Zach’s management of her and their win even more impressive.

6. Drift Away, Under Pressure, and Safari Showdown

In season 22, episode 7, best friends Pam & Winnie had to pick between a Brains and Brawn Detour. Brains required players to go out on a horse safari looking for ten different animal cutouts. Brawn had teams stacking traditional barges with wood while placing a carrot in front of the horse leading the barge to help the horse to get moving towards their destination.

Pam & Winnie chose Brawn and worked hard on loading the card. Unfortunately, they had no luck getting their horse to move an inch. After a while, the team chose to switch Detours with Winnie declaring, “We heavily prepared for his race, but what you can’t prepare for is that feeling of anxiety and that pressure.”

After switching Detours, Pam & Winnie began searching for the ten animal cutouts. Pam & Winnie tried once to get the correct answer and failed. They tried again, as other teams passed them. After guessing wrong again, the women switched back to the first Detour option. Finally, they complete this task, but not after losing a lot of time, too much time to recover from. Pam & Winnie were eliminated in this leg of The Amazing Race.

Pam & Winnie

Pam & Winnie

7. Ready, Aim, Fire!

In season 17, episode 1 home shopping hosts Brook & Claire were holding in tough in the competition. When arriving at the Roadblock, Claire volunteered because she thought it involved riding horses. Instead, the Roadblock had players using life-sized shotputs to shoot watermelons at suits of armor. If a player could knock the suit of honor over, they would complete the Roadblock.

Claire was gungho to complete the Roadblock. Unfortunately, in the process of firing the watermelons, Claire shot one that ricocheted directly into her face. Claire had to seek medical attention, but she persevered and Brook & Claire managed to avoid elimination despite this serious injury.

8. Say, Cheese!

In this task, teams had to take 200 pounds of cheese in 50-pound wheels up a steep slope using rickety equipment. Even worse, they had to then go back down the hill, whose slippery slope proved hazardous. Father-son team Mel & Mike had some troubles with Mel pulling a groin muscle while he struggled to control the giant wheels of cheese. Although Mel & Mike struggled mightily with this task, they did manage to survive the episode and continue on in the race.

9. Tea Tasting

This Roadblock took place on leg 6 of Season 18. The Roadblock actually began before the teams even knew it because early in the leg, while they were in Kunming, China, they tasted a specific tea at a tea shop. They then flew to Kolkata, India.

The Roadblock itself took place in Kolkata, where the racer doing the Roadblock had to bring a mango, papaya, and a brick of tea to a tea auctioneer. On tables in the hall were thousands of cups of tea – only a few of which were the same mango-papaya tea the racers had tasted back in China. The racers had to drink an entire cup of tea once they tried it. They completed the Roadblock once they found the correct tea and presented it to the tea auctioneer.

Mother and son team Margie & Luke had Luke do this task. Although it took most of the racers a long time to complete the Roadblock, it took Luke hour upon hour to finally find the right cup of tea and his disastrous performance resulted in the team's ignominious exit from the race.

Luke drinking hourse worth of tea

Luke drinking hourse worth of tea

10. Who’s Ready to Spice Up Your Life?

In Season six, leg eight of The Amazing Race, teams had to decide on who would do the Roadblock. The clue read, “Who’s Ready to Spice Up your Life?” This task turned out to require the player to eat a 24-ounce bowl of extremely spicy soup.

All of the teams doing this challenge struggled to choke the soup down. Victoria was doing the task for Jonathan & Victoria and she kept puking up mouthfuls of soup, something the other racers definitely didn’t appreciate. Freddy was doing the task for him and Kendra and he managed to puke in the soup, and then was forced to continue eating it. Ew.

Gus & Hera got to the Roadblock last and Gus couldn't make any progress on that blazingly spicy soup. Because of that, they are eliminated on this leg. Even though Gus & Hera were the ones eliminated on this leg, this challenge was extremely difficult for all the players who downed the soup, with many throwing up and complaining about the severe burning from the soup’s spices.

Spicy Hungrian soup

Spicy Hungrian soup

The Most Memorable Amazing Race Challenges

© 2018 Teeuwynn Woodruff

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