Ken Jennings throws a playful jab at rival during ‘Who Wants to Be a Millionaire’ appearance

"Jeopardy!" host Ken Jennings already had a winning streak on the show as a flex. Now he has also added winning on “Who Wants To Be A Millionaire” to his list of achievements. It turns out that Jennings can be a cocky competitor as he reportedly rubbed the victory in one of his rivals’ faces.

Jennings wasn’t alone in his road to victory. He was paired up with critically acclaimed actor Matt Damon. The show was hosted by Jimmy Kimmel, which made things all the more interesting. Kimmel and Damon have had a faux rivalry for many years now, and the two have maintained their on-screen feelings of hatred towards each other for many years.

As per a TV Insider report, Jennings and Damon used the 50/50 and Ask The Host lifelines for the final couple of questions. The actor at first was reluctant to ask his arch-nemesis for help, but upon his partner’s insistence, he had to concede. Kimmel also loved the entire thing as he sat in the host’s chair and smiled as Damon was caught in a dilemma when it came to asking him for help.

In the end, they used the 50/50 lifeline to win the million dollars that went to Damon’s charity, Water.org. However, that is not the only two lifelines they used. As per a report in Variety, after winning the money, Jennings used the Phone a Friend lifeline to call up his longtime friend and “Jeopardy!” rival Brad Rutter. The 51-year-old then did a John Carpenter, who used the lifeline just to let the person on the other side know that they’d won $1 million.

Rutter and Jennings’s rivalry was the stuff of gameshow legend. It began in the Tournament of Champions in 2004 with $2 million up for grabs. The two faced off against each other and Jerome Vered. Rutter ended up winning all three games at the time. He also beat Jennings in the Battle of the Decades tournament in 2014 and 2019’s Jeopardy! All-Star Games. The 51-year-old exacted his revenge in the 2020 Greatest of All Time competition.

“We got to do the ‘Hey, Brad. We’re gonna win a million dollars!’ thing that John Carpenter made famous,” Jennings said. As per the “Jeopardy!” host, the hardest question of the evening was the one for $500,000. It was the same one that saw Damon reluctantly ask Kimmel for help. The question posed was which celebrity’s claim to fame was entering a Steve Martin lookalike contest.

Kimmel said the answer was Bill Nye, and it turns out that it indeed was the right answer. Safe to say that Jennings was impressed with his fellow host. “Neither of us had heard the fact about Bill Nye in a Steve Martin look-alike contest, and that was the one where I thought we might just have to go out here because we’ve never heard this, and a lot of the answers look appealing and plausible,” he said.

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