Ben Affleck and Jamie Ding

Playing to raise money for his Eastern Congo Initiative charity, Ben Affleck got a little help from recent Jeopardy! favorite Jamie Ding — but even those two smarties needed assistance from two lifelines (Ask-the-Host and Phone-a-Friend) to help them get to the winning answer. The question was in regards to the names of pairs of turkeys that had been pardoned by a U.S. president; in the end, host Jimmy Kimmel’s gut answer was the correct one.

Matt Damon and Ken Jennings

Affleck’s BFF Matt Damon had a similarly successful run on the show with another Jeopardy! champ, Ken Jennings, in 2025. Playing for Damon’s charity Water.org, the two picked the correct answer on the last question after playing a 50:50 lifeline: “Susurrus” is the sound that leaves make when the wind blows through them, and with that, Damon earned a “begrudging” handshake from longtime “enemy” Kimmel.

Oscar Nuñez and Kate Flannery

Guess they picked up a few tidbits around The Office! The show’s costars earned the million for Planned Parenthood and Philabundance during the 2025 season finale of the game show. Despite Nuñez being so nervous during the final question he had to lay down, the two took home the win on the question “The word ‘planet’ comes from an ancient Greek word that literally means what?”

Ike Barinholtz and Alan Barinholtz

Actor Ike Barinholtz had already established himself as somewhat of a trivia savant with his very successful run on Celebrity Jeopardy!, and his dad Alan was a lawyer before earning his own TV fame as the judge on Jury Duty. So they were a pretty well-matched duo to take on the computer in 2024, when they correctly identified a “zax,” the highest-valued three-letter Scrabble word. Their win went to fund an ASL Program at Los Encinos School.

David Chang

Chef David Chang made history as the first celebrity to take home the $1 million on a 2020 episode, donating his winnings to the Southern Smoke Foundation. He used his Phone-A-Friend to call Mina Kimes, an ESPN analyst (and eventual Celebrity Jeopardy! All-Stars winner herself) for help with his final question, about the first president to have electricity in the White House.

“She’s so much smarter than I am though. And she knows this stuff,” Chang explained to Kimmel of his decision to call on the last question. “I didn’t do well enough in school and I was a terrible student — that’s why I became a chef.”