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Macaulay Culkin nearly had a huge win on 'Celebrity Jeopardy' but $1 made all the difference

Culkin has been a clue on the game a whopping 42 times since he was a child star.
PUBLISHED MAY 27, 2025
Screenshot showing Macaulay Culkin on "Celebrity Jeopardy!" (Cover image source: YouTube | Jeopardy!)
Screenshot showing Macaulay Culkin on "Celebrity Jeopardy!" (Cover image source: YouTube | Jeopardy!)

As the lead actor of the classic "Home Alone" franchise, Macaulay Culkin made outsmarting burglars look like child's play. But the former child star couldn't get past the questions on "Celebrity Jeopardy!" Even though he seemed set for a big win, he fell short by just one dollar. Culkin’s name has been tied to the popular game show for many years, as he had appeared as a clue 42 times, according to a report in Exclaim.

He was up against fellow actor Rachel Dratch and WWE superstar Becky Lynch, and did a fantastic job leading up to the Final Jeopardy as he answered questions from various categories. However, one of his favorite ones was the ‘Six Degrees of Actual Bacon’ category, which had questions about dishes containing bacon. However, things did not work out in his favor in the final round.



 

The Final Jeopardy clue read, “Exhumed in 2017 to settle a paternity suit, his moustache had 'preserved its classic 10-past-10 position' according to the Spanish press." The correct answer was Salvador Dali, and all three contestants got it right. Culkin had won $16,800 until that point and had wagered all of it, which brought his total to $33,600. Dratch, however, had won $23,000 and wagered $10,601, bringing her total to $33,601, to make her the big winner of the day against Culkin by a single dollar. Dratch had thought that she had gotten her math wrong when it was time to reveal how much money she had wagered. Thankfully for her, that was not the case. She had lagged behind earlier in the show but did a great job with the daily doubles to end up in the lead in the final round.



 

For Culkin, the loss must have been disappointing, but he had a great time being a contestant on the show. The actor had also revealed that his fiancée, Brenda Song, had quizzed him relentlessly for practice ahead of the show. “Like, whether I was in the mood or not, she just kept on asking me questions [like it was] a normal day," the actor had said to host Ken Jennings.

"She threatened to bring them on the ride over here, and I was like, 'Enough is enough! I'm already nervous," he added. Jennings also asked him how he felt about being a clue on the show 42 times so far. The host even stated that he didn’t know if Culkin’s name would come up as a clue again. “That would make it so much easier. For real, I would be so much less nervous,” he said according to a report in the New York Post.



 

The actor was playing to win money for the San Diego Zoo and Wildlife Alliance. “I’m sure a lot of people are familiar with it, but it’s a place that’s near and dear to my and my family’s heart. They work on conservation and the relationship between wildlife and people, trying to make it better,” he explained.

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