I Had High Hopes For Ken Jennings On Who Wants To Be A Millionaire, But He Exceeded My Expectations When He Called Out A Lifeline Trap

Ken Jennings and Matt Damon compete on the Who Wants to Be a Millionaire Season 4 premiere on July 23, 2025.
(Image credit: Christopher Willard/Disney)

Spoiler alert! This story discusses the Season 4 premiere of Who Wants to Be a Millionaire, which aired on July 23. Stream the episode with a Hulu subscription if you don’t want to know how the celebs did.

A new season of Who Wants to Be a Millionaire is underway on the 2025 TV schedule, and the talent in the premiere was impressive to say the least. Ken Jennings brought Matt Damon out in a quest to donate seven figures to charity, and I admitted going in that I’d be disappointed if they walked away with anything less than $1 million. However, the Jeopardy! host ended up exceeding my expectations by avoiding one specific pitfall when it comes to the “Ask the Audience” lifeline.

As Jimmy Kimmel pointed out multiple times during the episode (in reference to his infamous feud with Matt Damon), Ken Jennings did not need a partner to help him on one of the best game shows of all time, but it’s certainly more fun to see the celebs have someone to talk out their answers with. However, that’s where many get in trouble with the “Ask the Audience” lifeline, and I was so relieved to hear Jennings say this upon seeing the $250,000 question:

I’ve got a feeling. If there’s any chance we’re gonna go ‘Audience’ here, maybe we shouldn’t hash it out too much, you know what I mean? Like, prejudice the audience toward one answer or another.

Ken Jennings, you are one of Jeopardy!’s biggest winners for a reason. This has been a huge pet peeve of mine on Who Wants to Be a Millionaire, hearing the celebrity contestants explain all the reasons why they’re leaning toward one answer or another before asking the audience what they think. OF COURSE, they’re going to second-guess their own knowledge and go with the celeb’s logic.

Matt Damon and Ken Jennings, however, kept it quiet, with the Jeopardy! GOAT deciding:

Let’s ask the audience, then once the votes are in, we can speak freely.

Jimmy Kimmel praised their “smart strategy” of not leading the audience in a specific direction by sharing their thoughts out loud, and it worked! The audience collectively confirmed what Ken Jennings and Matt Damon were both thinking. If they’d talked it out beforehand, there would have been no way to know if the audience members actually knew which animal engaged in “vertical sleeping” or if they were just trusting the smarts of the celebs on stage.

This very issue plagued Drew Carey and Aisha Tyler in the first half of Who Wants to Be a Millionaire’s premiere. This was another pair who had the potential to go the distance, with Carey winning $500,000 in his first appearance on the show back in 2000 and Aisha Tyler competing on Celebrity Jeopardy! multiple times.

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However, they talked at length about their $32,000 question and whether Whitney Houston, Celine Dion, Tina Turner or Britney Spears had more No. 1 Billboard Top 100 hits and even almost picked Spears before turning to the audience for help. I was shouting at the TV not to do it, and of course, the “Toxic” singer got the majority of the poll responses (rather than Houston), handing the Whose Line Is It Anyway? hosts a quick exit.

Jimmy Kimmel joked that he blamed the audience for leading them astray, but Drew Carey recognized their mistake, saying:

I think we talked them into it.

I’m so glad Ken Jennings and Matt Damon didn’t follow suit. As for whether they took home the million, we’ll have to wait and see. The episode ended ahead of their $500,000 attempt, so tune in when Who Wants to Be a Millionaire returns at 8 p.m. ET Wednesday, July 30, on ABC.

I’m just hoping that future contestants are paying attention and will follow Ken Jennings’ Millionaire strategy.

Heidi Venable
Content Producer

Heidi Venable is a Content Producer for CinemaBlend, a mom of two and a hard-core '90s kid. She started freelancing for CinemaBlend in 2020 and officially came on board in 2021. Her job entails writing news stories and TV reactions from some of her favorite prime-time shows like Grey's Anatomy and The Bachelor. She graduated from Louisiana Tech University with a degree in Journalism and worked in the newspaper industry for almost two decades in multiple roles including Sports Editor, Page Designer and Online Editor. Unprovoked, will quote Friends in any situation. Thrives on New Orleans Saints football, The West Wing and taco trucks.

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