These Were Norm Macdonald’s Funniest Answers (and Jokes) on ‘Who Wants to Be a Millionaire’

In the year 2000, Who Wants to Be a Millionaire was the biggest game show on TV. Like all popular game shows, it wouldn’t be long until they cranked out a celebrity edition of the show. In fact, it debuted that same year. For Celebrity Millionaire’s second week, the contestants were a truly eclectic group — a group that included Tyra Banks, Vivica A. Fox, Alec Baldwin, Charlie Sheen and disgraced rapper P. Diddy. There were also a host of comedians, the most memorable of which was Norm Macdonald, who was the very last to compete for his charity.
It was worth the wait, however, as Macdonald cranked out a number of hilarious zingers during his short stint on the show. Here are his 10 funniest jokes and answers…
“You know, if this was me I would keep going, but there’s children… Give me that $100!”
After answering the very first question correctly, Macdonald jokingly bailed out of the rest of the competition by asking for just the $100. Fortunately, he was only kidding.
“I know ‘Larry King Live’ is on The WB.”
One of Macdonald’s few SNL impressions was Larry King, which made it rather surprising when he got the question, “Larry King Live currently airs on what TV channel?” His choices were “A: MSNBC,” “B: CNN,” “C: ESPN” and “D: The WB.” Thinking about the question, Macdonald responded, “I know The O’Reilly Factor is the Fox News Channel. I know that Hardball with Chris Matthews is MSNBC. I know that SportsCenter is ESPN.” Finally, before answering “B: CNN,” he jokingly said, “I know Larry King Live is on the WB.”
“My charity today is the Palm Beach Tennis and Golf Resort.”
In reality, Macdonald was playing for Paul Newman’s children's charity The Hole in the Wall Gang Camp, for whom he won $500,000.
“See, here’s the problem. Let’s say I lose all that money and it gets back to Paul Newman…”
Macdonald’s final question was, “During the Cold War, the U.S. government built a bunker to house Congress under what golf resort?” Instead of going forward, he stopped and left with $500,000, in part because he said he feared the wrath of the then-still-alive Paul Newman.
“Well, I don’t know anything about music, but I would imagine it would be a guitarist.”
This was Macdonald’s perfect answer to the following question: “In 1999, who raised more than $5 million for charity by auctioning off 100 of his guitars?”
Questioning the Show’s Integrity
When Macdonald got to the question for $250,000, he was asked, “The Reina Sofia Art Center is located in what European city?” At first, Macdonald was waffling between “A: Madrid” and “B: Lisbon,” but before going to a 50/50 lifeline, he asked host Regis Philbin if there was “some dude back there” who, seeing that he’d narrowed it down to these two, would intentionally leave only these two when he used the lifeline. Regis swore that there was no such “dude” backstage and the answers that would be eliminated had been “locked in for months.” So, Norm used the lifeline and, sure enough, only “A: Madrid” and “B: Lisbon” were left, resulting in the night’s biggest laugh.
“Could I ask only the of the audience who for sure know the answer?”
Macdonald ended up using a lifeline on the guitar question, deciding to ask the audience.
“I’m pretty sure it’s the Southern Cross, Reeg, but then I looked in your eyes and you did some freaky face.”
When he got to the question for $125,000 — “Sailors in the Southern Hemisphere use what feature in the night sky to aid in navigation?” — Macdonald really started to feel the heat. He even used a lifeline when he called Simpsons writer Sam Simon, who confirmed that the Southern Cross was correct.
“That’s very uninteresting!”
Macdonald’s best line of the entire night came after the guitar question for $64,000. After getting the answer (Eric Clapton) correct, Regis shared a factoid with the audience, saying, “The guitar used to record the entire ‘Layla’ album sold for almost a half million dollars.” To that, Macdonald delivered a deadpan, “That’s very uninteresting,” which seemed to surprise Regis, as he awkwardly responded with, “You’re probably right.”
Bringing Kato Kaelin
The funniest thing Macdonald did on ABC’s Who Wants to Be a Millionaire probably went over a lot of people’s heads. Macdonald had notoriously been fired from Saturday Night Live by NBC head Don Ohlmeyer for his relentless jokes about O.J. Simpson. So, a few years after his dismissal, when Macdonald had a platform on the biggest game show on TV, he brought along a star witness who testified against Simpson. Macdonald claimed Kaelin was just his friend, but it’s much more likely that Macdonald was fucking with his old boss.