Phil Keoghan Shares His Favorite Amazing Race Moments

A look back at 30 seasons of milestones, million-dollar mistakes, and heart-pounding finishes to the Pit Stop on The Amazing Race.

The best of The Amazing Race—as chosen by the guy who's seen it all—Phil Keoghan.

The best of The Amazing Race—as chosen by the guy who's seen it all—Phil Keoghan.

After 18 years of world travel and weird challenges, The Amazing Race remains the gold standard in reality competition.

Phil Keoghan has been to 90 countries—and racked up 981,000 frequent flyer miles—hosting The Amazing Race (TAR). And as the beloved and multiple Emmy-winning reality competition series enters its 31st season, neither its host—nor the show itself—shows any signs of slowing down. We look back at 30 seasons of milestones, million-dollar mistakes, and heart-pounding finishes to the Pit Stop.

Get the whole story in the May-June 2019 issue of Watch!—on newsstands now!

Photography by John Paul Filo/CBS.

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"Swing, You Fat Bastard, Swing!"

The iconic line from the pilot—delivered by Kevin O'Connor to fellow frat bro Drew Feinberg at the zip line Detour—helped kick-start The Amazing Race. "We had no idea what had hit us," Phil Keoghan says.

Photography by Tony Esparza/CBS.

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"We Got a Foot Race Right Here"

In The Amazing Race 2, Wil Steger stood less than 100 yards from the finish line, calling out to lagging teammate Tara Lynch and allowing lifelong friends Chris Luca and Alex Boylan to overtake the separated couple. "The closest finish I'll never forget," says Phil Keoghan.

Photography by Tony Esparza/CBS.

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"Should I Just Go Naked?"

In The Amazing Race 4, Jon Corso didn't want to get his underwear wet to retrieve a rock at a Roadblock, "so he bared it all to complete the challenge in Hawaii!" Phil Keoghan remembers. "Look at that big ... rock!" teased Jon's fiancé, Kelly, as he emerged from the beach, clue in hand.

Photography by Travis Pierson/CBS.

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"My Ox Is Broken!"

During the "Plow" Detour in The Amazing Race 5, Colin Guinn had an infamous meltdown, blaming his beast of burden for his inability to find the clue in the mud. "It's a classic!"

Photography by Travis Pierson/CBS. 

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"Put Them on My Shoulders!"

The Amazing Race 5's Charla Faddoul wanted to "show ... what I can do and break all stereotypes about dwarfs." When cousin Mirna struggled to carry a 55-pound slab of beef, Charla threw it on her back and carried it half a mile. "Charla showed a never-die attitude" says Phil Keoghan.

Photography by CBS.

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"Who's Got Hay Fever?"

In The Amazing Race 6, 20 clues were hidden in 270 bales of hay. Lena Jensen spent a fruitless eight hours searching for one, leading to the elimination of her and her sister, Kristy. "This challenge not only broke them," says Phil Keoghan, "but inspired us to bring it back on a future season."

Photography by Tony Esparza/CBS.

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"Paolo Family ... You Look Ridiculous"

In The Amazing Race 8, the last family to arrive at a Pit Stop had to give up everything but the clothes on their backs. "The Paolo family checked into the Pit Stop trying to wear every article of clothing they brought," Phil Keoghan remembers. The kicker: The Paolos turned out not to be last.

Photography by Robert Voets/CBS.

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"I Don't Have Rhythm, Obviously"

"Andrew [Lappitt] and Dan [Honig] marching in Russia—pure comedy," Phil Keoghan says. The frat boys from The Amazing Race 13 choose Boots over Borscht and had to learn a traditional Russian military march.

Photography by Monty Brinton/CBS.

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"Don't Let a Cheese Hit Me!"

In The Amazing Race 14's premiere, teams had to carry wooden cheese racks up a steep hill in Switzerland—then transport four 50-pound cheese wheels back down. The result: "The locals rolled with laughter as teams lost control of their cheddars in spectacular fashion."

Photography by CBS.

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"Right in the Kisser"

In The Amazing Race 17, Claire Champlin tried to launch a watermelon with a medieval slingshot, only for it to backfire—right back in her face. "The video says it all," says Phil Keoghan of the footage, which went viral, racking up over 6 million views on CBS' YouTube channel alone.

Photography by Jeffrey R. Staab/CBS.

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"You're a Warrior! You're a Champ!"

Phil Keoghan says of The Amazing Race 29: "Watching a wounded warrior and former U.S. Navy corpsman [Redmond Ramos, who has a carbon-fiber leg] run up hundreds of stairs with his teammate, Matt [Ladley], to win the 10th leg in Vietnam was unforgettable."

Photography by CBS.

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