10. The Chocolate Factory – Season 5, Episode 3
Fans (and fellow contestants) either loved cousins Charla and Mirna or loved to hate them. Despite her small stature, Charla proved her strength and endurance time and again, doing everything from shouldering a giant slab of beef to chowing down on thousands of pieces of chocolate in search of one with a white center. Something about Charla in that hat eating chocolate after chocolate can’t help but bring to mind this classic I Love Lucy episode.
9. The Highest Jump – Season 11, Episode 11
When the All-Star teams arrived at the Macau Tower roadblock, they learned that one team member had to walk around the 1,109-foot-tall structure’s external observation deck—and then sky jump off of it. “It’s a little slick out here,” said beauty queen Kandice. “I can’t believe I’m doing this!” said Charla.
8. The Taxi Bill – Season 7, Episode 12
Married couple Uchenna and Joyce were thisclose to winning their season, just feet away from the finish line… but they’d run out of money to pay the cab driver who’d driven them there. Rather than ditch the guy, they went around begging strangers for cash, knowing they were just $25 away from $1 million. Uchenna and Joyce weren’t about to start playing dirty right at the end, though; they managed to pay their fare and still win the big prize.
7. The Chaos of Color – Season 13, Episode 7
The roadblock requiring racers to participate in the traditional Indian Holi festival—which involved getting pelted with lots and lots of dried pigment—proved a challenge for divorcees Kelly and Christy. Kelly prolonged the task by misunderstanding the directions, and Christy got a faceful of paint too, for good measure.
6. The Water Slide – Season 15, Episode 6
Harlem Globetrotters Flight Time and Big Easy arrived at this roadblock as newly dating couple Canaan and Mika were having some, um, issues with the super-size water slide. Canaan tried cajoling, bullying, and reasoning with Mika, but then Big Easy played into her fear of heights and psyched her out. “If you’re scared, don’t do it, Mika,” he said. “Don’t hurt yourself, baby.” Canaan and Mika lost their place, allowing the Harlem Globetrotters to go down first and avoid elimination.
5. The Shove Heard ‘Round the World – Season 6, Episode 5
With that leg’s pit stop in sight, married entrepreneurs Jonathan and Victoria were ahead of engaged models Freddy and Kendra. When Jonathan dropped his pack on a busy street, Victoria stopped to pick it up and struggled to carry both bags, allowing Freddy and Kendra to arrive first. Jonathan shoved a weeping Victoria on their approach to the mat; the two squabbled incessantly all race long, and Jonathan’s aggressive behavior toward his wife made him the villain of the season.
4. The Great Manipulation – Season 7, Episode 3
When “Boston” Rob Mariano realized he wasn’t going to be able to complete the roadblock—eating four pounds(!) of meat—he decided that he would skip the task and incur the four-hour penalty time. But rather than suffer alone, the king of reality TV competitions (two seasons of Amazing Race and four of Survivor, including perhaps the best-played season ever) convinced two other teams to take the penalty as well, to ensure his and then-fiancée Amber’s safety.
3. The Race to the Finish – Season 2, Episode 13
The show’s closest-ever finale finish featured separated couple Wil and Tara neck and neck with lifelong friends Chris and Alex. When he realized that they wouldn’t win in a footrace, Wil devised a plan to confuse the other team by getting out of their taxi at the wrong destination. It didn’t work. Wil and Tara just lost time, and when they arrived shortly before Chris and Alex at the final pit stop, the two guys quickly passed Tara—and won the race.
2. The Head Shaving – Season 7, Episode 8
Uchenna and Joyce’s fast forward required them both to experience a traditional Indian head shaving. Since Uchenna was already bald, he was exempt, but losing her long braids was a major emotional challenge for Joyce. Uchenna supported her through the whole thing, and when he told her afterward that she looked beautiful, she believed it (and we agreed). “It seemed like there was this blossoming happening with Joyce,” Uchenna said about the experience. “The more the hair came off… she just got brave, and I was overwhelmed with pride.”
1. The Melon to the Face – Season 17, Episode 1
In this roadblock, racers had to take down a medieval knight with watermelons and a giant slingshot. “Right in the kisser,” home-shopping television host Brook told her partner and cohost Claire, who took the advice to heart; she launched a melon that ricocheted right back at her and splatted her full in the face. Ouch! Brook came over to make sure she was okay before sending her back out there to complete the task.