Jimmy Kimmel’s Worst Nightmare Becomes a Reality on ‘Who Wants To Be a Millionaire’ When Ken Jennings Sides With His Enemy

Who Wants to Be a Millionaire season premiere kicked off on a hilarious note when Jeopardy! host Ken Jennings shocked host Jimmy Kimmel by bringing “arch nemesis” Matt Damon onstage as his surprise trivia partner.

Damon and Kimmel have had a longstanding fake feud, which started as a late-night joke when Kimmel repeatedly ended Jimmy Kimmel Live! by saying he had to bump Damon as a guest. Over the past few years, the joke feud ended up in comedy routines and roasts, often involving Ben Affleck. Damon’s unexpected arrival reignited the legendary rivalry, “blindsiding” Kimmel and nearly turning the game into a full-blown comedy sketch. But did trivia king Jennings and Kimmel’s arch-nemesis leave victorious?

The ‘Millionaire’ Premiere Reignited An Old Feud Between Jimmy Kimmel and Matt Damon

Having his rival on the stage allowed Kimmel to truly sharpen his tools, and his rapid-fire insults towards Damon significantly livened the gameplay. When a clue came up about A Minecraft Movie, Damon claimed he was too busy on set to have seen the film yet, while Kimmel quipped that “the good people” in the room already had. Jennings then asked why he was suddenly the target of Kimmel’s insults, to which the late-night host replied it was because he’d been the one to bring Damon, a “scroungy animal,” referencing the actor’s lengthy beard for his current role in The Odyssey, onto the show.

Kimmel acted betrayed by Jennings for secretly joining forces with his nemesis, and took every opportunity to insult the actor’s intelligence and point out his inability to weigh in on certain clues. He asked Damon if that was how things would normally work when writing with Affleck, letting his partner do all the work. When Kimmel ran out of this kind of banter, it was right back to mocking the beard, making the comment that Damon looked “like a homeless wizard.” In spite of Kimmel’s “attacks,” Jennings and Damon swept the board all the way up to the $250,000 mark, before the timer ran out, ending their run on the premiere episode with their earnings going to the charity water.org. This means that the pair will continue next week, ensuring Kimmel will have to put up with Damon’s presence on his stage for yet another episode before the pair cash out for their charity.

‘Millionaire’s Fourth Season Is Off to a Strong Start

While it was Jennings and Damon who stole the show in the premiere episode of the season, they weren’t the only celebrities to grace the stage. The episode opened with an unexpected pairing: comedian Drew Carey and actress Aisha Tyler took the stage together. To make their connection clear, Carey clarified that they both share the same agent, and have each hosted the series Whose Line Is It Anyway? Tyler also commented that she felt like she and Carey were like siblings, before pointing out she had worn her reading glasses to drive the comparison home.

Carey and Tyler worked seamlessly together, right up until the $64,000 that asked them to answer which pop-diva had 11 #1 top 100 hits: Whitney Houston, Celine Dion, Tina Turner, or Britney Spears. Carey seemed to be leaning toward Houston, whereas Tyler sided with the audience poll that favored Spears, locking in the incorrect answer that cost them their chance to move forward. Despite their loss, the mismatched pair still ended up earning $32,000 for their charities, International Rescue Committee and La Maida Project. When Jennings then joined Kimmel on stage, the late-night host joked that the last time they saw each other socially, the Jeopardy! host told him that he thought Millionaire was the more challenging of the two quiz shows. Viewers will have to wait until next week to see if having Damon at his side was enough to even the score.

Who Wants to Be a Millionaire airs Wednesday night at 8 p.m. ET/PT on ABC.