‘Wheel of Fortune’s 10 Most Memorable Puzzles of All Time
Wheel of Fortune‘s been known to stump a player or two with its complex puzzles, but other times it can be a breeze for the most well-versed competitors.
Delivered with the help of Pat Sajak and Vanna White, the puzzles can leave quite a memorable impression on viewers. Below, we’re rounding up 10 of the most notable puzzles from the game show so far.
This is an excerpt from TV Guide Magazine’s Wheel of Fortune: Farewell, Pat Sajak issue. For more inside scoop on the long-running game show and Pat’s final episode, pick up a copy of the issue available on newsstands and for order online at WheelofFortuneMag.com.
I’M HAVING A BALL
Back in March 2020, no one was having a ball. COVID had forced professional athletes to pack up their gear and go home. That left us stuck in lockdown with no highlight reels, no heroes to root for. Enter avid outdoorsman Mark Franco. The Brentwood, California, resident had a rocky start in the Triple Toss-Up—where three consecutive puzzles have a similar theme—failing in the first round to “Get the Ball Rolling.” Someone should have told him to “Keep Your Eye on the Ball” (the second-round answer). Then, in round three, with only a single G on the board, he triumphantly declared “I’m Having a Ball!” Mark walked away with a $7,000 trip to London and $2,000 in cash.
I’VE GOT A GOOD FEELING ABOUT THIS
When 26-year-old fashion editor Caitlin Burke made this one-letter solve, she knew for certain that her answer was the right one. “There are a million things I’m not good at,” she said after her $53,000-plus win in 2010. “But Wheel of Fortune, I can do.” With just an apostrophe and an L, the puzzle prodigy used process of elimination to come up with “I’ve Got a Good Feeling About This.” The audience couldn’t believe it. Even host Pat Sajak was speechless, later calling it “the most amazing solve we’ve ever had.” It wasn’t so amazing to Caitlin, who’d trained her mind to tackle tricky puzzles. “I believe that luck is preparation meeting opportunity,” she said.
COUNTRY ROADS TAKE ME HOME
Recent USC grad Sam Lundquist must have been a big fan of John Denver’s country classic “Take Me Home, Country Roads” to nail this one so quickly in 2007. For a Speed-Up puzzle (when contestants have three seconds to say the answer), Sam guessed its iconic lyrics with nothing but an N and two Ts. Those country roads would ultimately take Sam to Greece—he won a trip to Athens—where he’d likely send home a “Postcard of the Parthenon” (another puzzle he solved that night). We don’t know about him, but if it were us, we’d have hit Athens’ best karaoke bar to belt out “Country Roads, Take Me Home”!
THE THRILL OF VICTORY AND THE AGONY OF DEFEAT
This is the big one. The colossal fail so chock-full of cringe, it made this writer sit up from his laptop and say “Woof!” aloud. In 1985, fashion instructor Terry Warden went on one of the craziest spinning streaks in Wheel history. As the board filled in, everyone caught on. Except for poor Terry. Consonant after consonant, she begrudgingly declared, “I have to spin.” And with each of her mind-blowing nine turns of the wheel (four landed on $5,000!), the entire studio grew more exasperated. Sajak’s voice cracked as he read the whopping total she’d banked: $62,400. It would have—should have—been the single largest one-round win to this day. But Terry needed that 10th spin. She biffed it with S, competitor Niki called L, and that was that. Sajak said it best then and there: “Oh, boy. Well! There’s an ironic puzzle there, isn’t it? My goodness.”
THE COAST IS CLEAR
Warning: nautical puns dead ahead! You’d think a Navy officer would have had his sea legs, but Kareem Tate was sunk more than once in this 2002 episode. Good thing he was a mechanic and not in charge of spotting enemy ships: The coast was not clear when he whiffed the opening Toss-Up to determine who’d have the first spin, suggesting “The Coast in India.” That had us all at sea, but we practically fell overboard when he mistook “Fingers & Toes” for “Miners & Hoes.” Even Kareem’s long-shot guess of an M in “Winning the Office Super Bowl Pool” didn’t keep him afloat. But Tate didn’t let his many misfires take the wind out of his sails. He kept an even keel and righted the ship, landing on “Tripoli” for $25,000 in the bonus round.
REGIS PHILBIN & KELLY RIPA
Unfortunately, game show legend Regis Philbin and his talk show cohost Kelly Ripa never competed on Celebrity Wheel of Fortune. But the duo did make an infamous appearance on the board in 2010. The category might have been Proper Names, but none of the three contestants, military men George, Shane, and Lee, could pronounce Regis’ or Kelly’s names properly! They called Reeg “Philbrin” and “Philmin.” And dubbed Kelly “R-ee-pa.” Even when the puzzle was completely filled in, one of them managed to pronounce it Kelly R-eye-pa! It took five guesses until they got it right. Our conclusion? The troops need to watch more daytime talk TV and reruns of Who Wants to Be a Millionaire.
MAGIC WAND
For every incredible solve that has to be seen to be believed, Wheel of Fortune has given us dozens of debacles we can’t believe we’ve seen. Which is the funniest? It has to be this 2012 puzzle that seemed like a no-brainer. College student Zach Barron made it all the way to the bonus round. So he shouldn’t have needed any sorcery to solve this one. Especially when every letter he called out was on the board. With just two blanks, he managed to name all sorts of “Magic” things: “Magic Band,” “Magic Hand,” even “Magic Sand.” But he was so spellbound by the rhyme, he couldn’t see the true answer: “Magic Wand.” The loss may have cost him a Prius, but don’t feel too bad for Zach. He still walked away with $19,950.
PRISTINELY
Megaword was an ill-fated bonus category of extra-hard single words that gave solvers the opportunity to earn an additional $500 if they could use it in a sentence. It was infamous for stumping contestants and taking way too long to solve. Years later, Sajak declared, “I hated every moment of it.” The worst example has to be this 1994 Megaword, which could not have gone less “Pristinely.” La Shawn Robinson completed the board, but then pronounced it “prista-nelly.” Fellow contestant Ina, who had $0 in the bank, said it correctly for $200 and earned the extra $500, but Sajak seemed skeptical that her sentence—“She carried herself pristinely”—deserved the bonus. As he cut to a commercial, he could be heard sarcastically saying, “The always exciting Megaword.” When the show returned after the break, he introduced himself as Pat “I’m Only the Host” Sajak. Suffice it to say, Megaword did not survive past the 1994–95 season.
A GROUP OF WELL-WISHERS
Here’s a classic! The category was People, and Joseph Cardone (near left) managed to get the first half in this 1999 episode. But instead of “Well-Wishers” he went in a less wholesome direction. Joseph’s guess of “A Group of Pill-Pushers” has got to be one of Wheel’s all-time best wrong answers. It had a laughing Sajak shouting, “This is Wheel of Fortune, Joe!” and then jokingly pretending to close the show with a “Good night everyone!” It didn’t help that the next contestant answered “A Group of Will-Wishes” before the third player finally got the solve.
QUITE FRANKLY
In Sajak’s 43 years hosting Wheel of Fortune, we’re fairly certain this 2021 blunder is the only time he accidentally solved a puzzle himself. Contestant Jeffrey Knight (inset) had a rough bonus round ahead of him, leading the sympathetic host to say, “Well, I’d rather be standing here than there, quite frankly.” If only Jeffrey had been listening more closely! But we don’t blame him. The bonus round is a high-pressure situation, and his focus wasn’t on Sajak, quite frankly. When they came back from break, White pointed out Sajak’s blunder, leading him to close the show by declaring, “It’s funny what your mouth will say that your brain says, ‘You shouldn’t do that.’ Anyway, we’ll quite frankly see you next time!”
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