ECONOMY & WORK
MONEY 101
NEWS
PERSONAL FINANCE
NET WORTH
About Us Contact Us Privacy Policy Terms of Use DMCA Opt-out of personalized ads
© Copyright 2023 Market Realist. Market Realist is a registered trademark. All Rights Reserved. People may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.
MARKETREALIST.COM / ECONOMY & WORK

'Jeopardy' host Ken Jennings reveals one major regret during his iconic winning streak

In a recent video on Instagram, the current host of the show harshly criticized his own clothing choices.
PUBLISHED SEP 30, 2025
Ken Jennings on 'Jeopardy!' 2025 (Cover Image Source: YouTube | Jeopardy!)
Ken Jennings on 'Jeopardy!' 2025 (Cover Image Source: YouTube | Jeopardy!)

Ken Jennings had arguably the greatest run of all time on "Jeopardy!" Back in 2004, the current host of the show was a contestant, and he went on to record a 74-game winning streak. No one has even come close to breaking that record since. It is something that Jennings must be mighty proud of. However, not every aspect of that historic run was good, according to the host. Recently, he revealed that he was disappointed with his choice of clothes at the time.

Jennings was not happy with his fashion choices, as per a report in E! News. He recently shared a video on Instagram, critiquing the clothes he wore on the show as a contestant. The first outfit was a beige shirt and a Coca-Cola-patterned tie. “If I’m seeing that right, that is a terrible tie and really it’s a color of shirt I would never wear. I guess if you like Coca-Cola, you’re into that outfit. That’s really unfortunate,” he said.

He also said that it would have been better had he worn a sweater over the shirt. The next look was of him wearing a cream-colored shirt with a pinstripe jacket and, once again, a colorful tie. Jennings liked the fact that he wore a jacket in this one, but was not a fan of the tie here either. He said that he had purchased it for cheap when he lived in South Korea.

Ken Jennings during his time as 'Jeopardy' player (Cover Image Source: YouTube| Jeopardy)
Ken Jennings during his time as 'Jeopardy' player (Cover Image Source: YouTube| Jeopardy)

“A lot of these were just kind of cheap dollar ties, probably from when I lived in Korea, and you could get knockoff clothes for cheap. I bet no tie here costs more than $3 American, and it really shows,” Jennings explained. Next up was a picture of him in a dark red shirt with a horizontally patterned tie, but the “Jeopardy!” host was not a fan.

“Horizontal stripes, so it’s not exactly slimming. It does go with the shirt, but in an unpleasant way. Looks like I’m wearing the Empire State building on my chest,” he added. This was followed by a picture of Jennings in a striped shirt, a checkered tie, and a plain jacket, which he believed was an okay look. However, the 51-year-old was not a fan of his facial expression.

Screenshot showing Alex Trebek and Ken Jennings on Jeopardy! (Image source: YouTube/ABC)
Screenshot showing Alex Trebek and Ken Jennings on Jeopardy! (Image source: YouTube/ABC)

“Look at that thousand-yard stare,” he said. “That is actually an okay look. It’s just a nice striped shirt. The checkered tie is alright, but it looks like some kid wearing his dad’s clothes and not blinking.” Next up was a bright yellow shirt and a tie with what seemed like several faces on it. Jennings said that he was surprised the showrunners let him wear that on the set.

“I think I was just trying to vary as much as possible because I thought, ‘Oh, you don’t want to wear the same six shirts, the audience will catch on to that.’ So instead, I wore new, worse shirts,” he added.

More on Market Realist

'Jeopardy' fans left fume as controversial ruling on James Bond answer robs champion of win

'Jeopardy' contestant shares her emotional BTS experience after making it to the show

'Jeopardy' shares stunning photos of how the set has changed from 1984 to today

RELATED TOPICS JEOPARDY
MORE ON MARKET REALIST
It's not the best look for ByHeart, the company producing and selling the baby formula.
1 hour ago
She had won more than $30,000 leading up to the Bonus Round, which was a great feat.
2 days ago
The bird's stock in the US is the lowest of the last 40 years thanks to a deadly avian flu.
2 days ago
The company claimed that there were concerns about physical safety with the bottles.
2 days ago
Currently, arguments about the legality of the President's tariffs are being made and heard.
2 days ago
She composed herself just well enough to be able to thank host Drew Carey after her big win.
2 days ago
The contestant was flexing his muscles and the host might have taken offence at that.
3 days ago
A lot of people would have wanted to swat the creature had it sat on their bodies out of fear.
3 days ago
The 1979 contestant had won a car during her time on the show, but her student failed to do so.
3 days ago
The company has issued an apology in a statement for the inconvenience caused.
3 days ago
Michael Burry made a return to X with a cryptic message warning against the 'AI Bubble'.
3 days ago
The host had no idea what the contestant was saying until he cleared it up.
4 days ago
Ryan Seacrest was surprised that the contestant was able to get it right so quick.
4 days ago
The creator claimed that it was all part of a bigger business model that got the bigger brands paid.
4 days ago
The group received massive backlash on social media from the show's fans for their trouble.
4 days ago
The two had become close friends during their time on the show, which saw Jennings become a legend.
4 days ago
The contestant had seemingly broken a few things that belonged to her father in her younger days.
5 days ago
At a price of just $4.99, the rotisserie chicken is one of the most popular Costco items.
5 days ago
The audience member let out a large cheer when a contestant said what an ex could teach a wife.
5 days ago
McMillon did not say that there were going to be layoffs, but that has been the theme at other places.
6 days ago