‘Jeopardy!’ Contestant Has Big Win After Taylor Swift & Drake Question

'Jeopardy!' contestants (from left) Madeline Kaplan, Jeremy Roberts, and Shannon Crisenbury, on May 5, 2026
Spoiler Alert
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It’s all coming back to them! One Jeopardy! contestant had a big win after correctly answering the final clue about Taylor Swift, Drake, and another singer.

Madeline Kaplan, from Toledo, Ohio, came into her second game with a total of $31,700. On May 5, she played against Jeremy Roberts, from Midhurst, Ontario, Canada, and Shannon Crisenbury, from St. Clair, Michigan. Warning: Spoilers for the May 5 episode of Jeopardy! ahead.

Kaplan, an editor, had the lead of $4,000 when she found the Daily Double on clue 11. She wagered all of her money in “Quotes About Science.” The clue read, “This astronomer wrote, ‘We’re made of star-stuff. We are a way for the cosmos to know itself.'”

“Who is Sagan?” she answered correctly. This put her in even more of a lead with $8,000. Roberts, a technology analyst, had $200. However, by the first 15 clues, Roberts had $2,200.

By the end of the round, Kaplan had $10,200. Roberts was in second place with $3,600. Crisenbury, a data annotator, finally got in the positives and ended with $3,400.

Crisenbury found the first Double Jeopardy DD on clue three. She had $5,000 and wagered $4,000. In “School of Lit,” the clue was “Sharing the title of a Dostoyevsky novel, this Elif Batuman book is about a smart but also clueless Harvard freshman.”

“What is The Idiot?” she answered correctly. This gave her $9,000.

Crisenbury then found the last DD on clue four. She wagered $5,000 in “Women & Photography.” The clue read, “Documentary photographer Mary Ellen Mark is perhaps best known for images of runaway teens on this city’s Pike St.”

“What is Seattle?” Crisenbury answered. She moved up to first place with $14,000. Kaplan still had $10,200.

Crisenbury had the lead by the end of the round with $19,200. Kaplan was not far behind with $18,600. Roberts was in third place with $7,200.

The category for Final Jeopardy was “The Canadian Album Charts.” The clue was “In 2025, Taylor Swift tied Drake & this singer for the most no. 1 albums on Billboard’s Canadian Albums chart, with 15.”

Roberts wrote, “Who is Celine Dion?” which was correct. He wagered $2,800, making his total $10,000. Kaplan’s response was “Who is Morissette?” She wagered $3,000, giving her $15,600.

Crisenbury had the correct response as well. She wagered all of her money, leaving her with $38,400. Crisenbury became the new champion and will return on Wednesday for game two.

“What an amazing game!” a Reddit user said.

“Fun games lately,” another wrote.

“Another fun game!” a third added.

Jeopardy!, weekdays, check local listings, stream next day on Hulu and Peacock

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