The Big 3-0

‘Jeopardy’ Turns 30: Watch Its Wackiest Moments (VIDEO)

Celebrating ‘Jeopardy!’s’ 30th anniversary by watching the show’s craziest and coolest moments.

Seth Wenig/AP

Thirty years ago, during the filming of a pilot that never officially aired, contestant Karen Muranaka chose the first-ever category of Alex Trebek's Jeopardy!: Lists for $25. The first-ever answer: Moses received this list on Mt. Sinai.

And it was contestant Jack Champion who first posed the proper question: “What are the Ten Commandments?”

Thirty years later, the show (a relaunch of an old show hosted by Art Fleming, which had run on and off from 1964 to 1979) is a phenomenon. Thousands upon thousands of (oftentimes useless) facts have been put out and millions of dollars have been won and lost, with quizmaster Alex Trebek there the entire time. And he has seen some things—fortunately keeping his sense of humor through it all. To commemorate the big three-O, we’ve compiled videos of some of the craziest answers, wackiest stories, and unforgettable people who helped make the iconic game show just that—iconic—for these past three decades.

Well, he was technically right.

This is a case of an amazing answer being shot down on the technicality that it wasn’t on Trebek’s cue card. Ken Jennings, who won for 74 straight days, pulling in over $2 million dollars, threw out this little gem in response to a question about a term that can be both garden tool and immoral pleasure seeker. The best part of the video is the brief pause before everyone realizes what Jennings had just said. Even Trebek was caught off guard.

Damn right he did.

The most recent video on the list, this excellent answer came from earlier this year during the Jeopardy! Teen Tournament. Leonard Cooper, who at the start of Final Jeopardy, had more money than both of competitors combined, answered the question in the best way he possibly could have (aside from, perhaps, getting it right).

A mustache more mighty than Trebek’s.

Frank Spangenberg, a member of the New York City Police Department (Transit Bureau) set a record way back in 1990, becoming the first person to win more than $100,000 in five days. Spangenberg has become something of a Jeopardy! legend, and in this interview years later, he talks both about the fame and about the game. Sure, this clip isn’t “wacky,” per se, but it’s uplifting and it shows some of the impact Jeopardy! has had beyond the set.

Guess she came to come in third.

After a pretty good streak, this woman bets it all, only to make a fool of herself when the big moment comes. The long pause after the question is asked is painful enough, but her smug expression is really the thing that sells it (and also likely the reason why Trebek decides to throw in a little jab at her after the fact). Just goes to show that arrogance definitely does not pay.

A computer plays Jeopardy! (and wins a million dollars).

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IBM’s Watson computer system was created for the sole purpose of playing Jeopardy!. It took on former winners Brad Rutter and Ken Jennings and won the million-dollar prize. This video is not really funny, and, depending on how you feel about the future relevance of the human race, you may find it somewhat disturbing. But whether you think it’s awesome or terrifying, it’s certainly fascinating. The bottom shows a little bit of what the computer is “thinking,” and although it doesn’t really explain anything about Watson’s process, it’s a cool little visualization of what answers Watson considered and how much it considered them.

Who says watching people through windows can’t be charming?

Reliably the most awkward part of each Jeopardy! episode—in the best way possible, is the contestant interviews, which range from charming to odd to, well, sometimes creepy. In this introduction, a contestant talks about her occupation and relationship. A teacher, she was dating the school’s custodian (she has gone on to marry him), but at the time his behavior was ... a little strange. So strange, in fact, that even her young students were confused by his constant staring through the windows as she was teaching. Trebek certainly was.

Wolf Blitzer just looks silly (on another network ... HEYO!)

Four years ago, CNN’s senior anchor Wolf Blitzer appeared on Jeopardy! alongside Andy Richter and Dana Delany. And while he may know all kinds of things about politics and whatnot, his performance shows that there is plenty of information he doesn’t know. The best bit is definitely when they have to take money back from him after realizing he had spelled something wrong.

And while we’re on the topic of celebrities failing at Jeopardy! ...

Remember when SNL was awesome?

Short, sweet, and to the point. Darrell Hammond’s performance as Sean Connery in the recurring SNL sketch Celebrity Jeopardy! was always great to watch. And its popularity went beyond just excellent parody, too, having been mentioned multiple times on Jeopardy! itself and featuring actual-host-Alex-Trebek on one episode alongside fake-host-Alex-Trebek-as-performed-by-Will-Ferrell. After enjoying this quick bit, feel free to ring in Jeopardy!’s big anniversary by going off into the Internet wilderness to watch all of Ferrell, Hammond, and Co.’s antics.

Correction: The original version of this story incorrectly stated that it was the Jeopardy!'s 30 anniversary on air. It's the 30th anniversary with Alex Trebek.