The moment came during Final Jeopardy with the clue, "These 2 foreign-born directors have each won 2 best director Oscars but none of their films has won Best Picture."
For this tournament, the contestants earn points in each game instead of dollars as in a regular "Jeopardy!" show. With two games in each match, the contestants' earnings are combined for a grand total at the end of each night. The one who wins three matches gets the $1 million prize.
Professional sports gambler James Holzhauer wagered 908 points on Final Jeopardy.
His response: "Who is the GHOST? (Greatest Host of Syndicated TV)
Actually, 'Jeopardy James' first started to write Pat Sajak's name, the host of "Wheel of Fortune."
To that, Trebek said, "I wished you had risked more points."
Rutter was up next. He wagered 4,133 points for his response.
First, Rutter wrote, "Ken es el hombre," translated from Spanish means fellow competitor Ken (Jennings) is the man.
But Rutter was not done. His response continued: "Eagles Super Bowl LII Champs."
The Eagles beat the New England Patriots 41-33.
Trebek laughed and said, "Ladies and gentlemen, I'd like to welcome you to the Jeopardy comedy hour."
"Go Birds!" Rutter said.
The correct response was, "Who are Ang Lee and Alfonso Cuarón?"
While Jennings also got it wrong (he did correctly guess Ang Lee), he won his second match.
"Jeopardy! The Greatest of All Time" continues Tuesday, January 14th at 8 p.m. ET/PT | 7 p.m. CT on ABC.