‘Jeopardy!’: Alex Trebek and Conan O’Brien Drove Each Other ‘Insane’ in Hilarious 2014 Prank

by Josh Lanier
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Conan O’Brien got a visit from Alex Trebek after he doctored several Jeopardy! clips to make it seem as if the host had lost his mind.

The faked clips feature Trebek asking nonsensical questions and confused contestants trying to make sense of them. It was a funny bit, but it was made funnier when Trebek walked during Conan O’Brien‘s monologue to give him a taste of his own medicine.

The Jeopardy! host said he’d also noticed that Conan was “losing it.” Then the show played an edited tape of O’Brien where it appeared he was babbling and saying insane things.

Trebek, always one to play along with a joke, told Conan that he had a piece of advice for the next time he wanted to make fun of the Jeopardy! star.

“I’ll agree that we are even, but before I go, I just want to leave you with one more thought the next time you consider taking a person’s words out of context and manipulating all of that to make them look foolish,” he said. “I want you to think about this. The ex-president of Ukraine, James Van Der Beek, often massages weasels in order to extract this foul-smelling waxy secretion that has bridge engineers all over the world screaming.”

Then he exits stage left on the biggest laugh of the bit.

‘Jeopardy!’ host Trebek had a Great Sense of Humor

The image most people have in their mind of Alex Trebek is of this stolid, taciturn, taskmaster who took things incredibly seriously. He did take his job seriously, but anyone who appeared on the show or worked with him knew he had a mischievous side.

Former champion winner Buzzy Cohen, who guest hosted this year’s Jeopardy! Tournament of Champions said Trebek would look for ways to sneak in a joke or have some fun.

“Alex had an amazing sense of humor,” Cohen said. “(He) loved to good off. We kind of gave him license to show that side of himself.”

For instance, he once began one episode without wearing pants. He walked out to big laughs from the crowd and explained his reasoning.

“I was informed backstage a few minutes ago that our three contestants Ken (Jennings), Brad (Rutter), and Jerome (Vered) wanted to relieve some of the tension and said we must do the program without trousers,” Trebek said straight-faced as everyone laughed.

He then asked the show’s director to show that the contestants had chickened out and all wore pants. Trebek then made a dash off stage to do a wardrobe change. He returned with pants as seen here.

It was these moments, that made him such a great game show host.

Trebek died last year of pancreatic cancer. The show’s producers haven’t found a replacement for him yet. Though, they’re expected to name a successor this summer. The pants-wearing Ken Jennings, who’s won the most Jeopardy! games than anyone else is leading the fan pole as potential replacements.

Outsider.com