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- When a contestant gets the answer wrong on the first question.
- Unless (starting with syndicated Season 9 of the US version) it's actually hard.
- More than once, a contestant has used the "Ask the Audience" lifeline, and gotten one hundred percent on an answer. That means, apparently, the only person in the entire set that didn't know the answer was the contestant in the hot seat. Every time, the host has cracked a fairly snarky joke at the contestant's expense.
- With the first few questions, it's common for Answer D to be the 'joke' answer. Sometimes these jokes can be funny in their own right. Here's a particularly funny example from one Meredith episode. The question asked which of the following phrases means 'I've had enough.'
- A - That's The Last Stick.
- B - That's The Last Leaf.
- C - That's The Last Straw.
- D - I'm Moving To Canada.
- During a Celebrity Millionaire episode, Norm MacDonald asked Regis if using a 50:50 after he said what he was deciding between would leave those exact choices, like there's some guy in the back trying to sabotage him. Regis assured him that the two choices had been locked in for months note ...but when Norm chose the 50:50 he was left with the two answers he was stuck between. Although the audience erupted into laughter, MacDonald gave Regis an absolutely majestic "WHADDID I TELL YA?" look. The whole ordeal can be seen here. (Of course, after the change to the 50:50 being "random", the computer left the answers the player was struggling between often enough that it led to the same allegations Norm brought up.)
Regis: Please, before you say "final answer", Norm, I'm not kidding. $468,000. Unless you're sure.
- When trying for the $1 million question, Norm contemplated one answer, and Regis spoke up Note :
Norm: Okay, fine, forget it.
Regis: I-it could be Pinehurst-
Norm: Just give me the half million, we'll quit.
Regis: All right, do you want to walk?
Regis: Do you, I have to find out if you want to walk away.
Norm: Well no, I'm trying to answer a question, but...
Regis: (holds up hands) I quit. It's too much for me, I can't stand it.
- On another Celebrity episode, Jon Stewart was playing for an Alzheimer's Association of America, which led to this Crosses the Line Twice exchange during the $250,000 question:
Regis: The Alzheimer's Association would get a quarter of a million dollars if you get this. And if you don't, they'll be back down to $32,000.Jon: Yeah, but they'd forget about it the next day.
- On another Celebrity Millionaire episode, Huey Lewis received exactly no help from the audience on a question.
- During the Super Millionaire spin-off period that started at $1,000 and ended at $10,000,000, Regis accidentally introduced a $20,000 question as if it was worth $20,000,000, and Hilarity Ensued.
Regis: Here we go for $20,000,000! (catches his mistake) A 20—?! I'm sorry! (audience cheers) Noooo, I take it back! "Rich jumped up!" "Really?!" Twenty thousand dollars...
- Another funny Super Millionaire moment is on the very first $500,000 question.
- An early contestant named Tom Coletta had this moment during his $8,000 question:
Tom: I'm a fat man, Regis! My heart can't take it!Regis: I'm just trying to help you sweat off a few pounds!
- The first contestant of the 10th-Anniversary Specials almost lost on her first question because of how suggestive it sounded at first.
- Also from the 10th-Anniversary Specials, Patrica Heaton's mathematics meltdown.
- During one of the Celebrity Millionaire episodes, Denis Leary was stuck on a question and used a Phone-a-Friend. When Regis asked who he wanted to call, Denis admitted he didn't even know the guy's name but knew he was from Harvard. Regis said, "We need a guy from Harvard, AT&T. Please help." When the phone picked up, Regis awkwardly said, "Hi, Regis Philbin calling from New York. Uh... are you from Harvard?" The man affirmed, and the audience giggled. Regis: "You mind telling us your name?" Man: "My name is David Blackmont." Regis: "Exactly the David we're looking for!"
Denis: ...Gene Hackman?? Gene Wilder.
- In the same game, Denis Leary got a question about which book contained a chapter named "I Am Born" (correct answer is David Copperfield), and one of the choices was Frankenstein. Denis said he never read Frankenstein, but said he saw Young Frankenstein. Regis added that he liked it too, and mentioned Gene Hackman.
Regis: Gene Hackman was in it too; he had a famous scene.
Denis: Gene Hackman was?? (realizes he's off-topic) All right never mind, we'll talk about that later.
Regis: Gene Hackman played the blind man.
Denis: Oh, that's right, you're right. (again realizing he's off-topic) I HAVE A LOT OF MONEY ON THE LINE!
- October 2, 2002: Minda Lopez takes way too long on a question, leading to large chunks of her ruminations being edited out, followed by captions of "much later" and "much much later". On a question further up, Minda begins mulling over her options again, prompting Meredith to pull a Screw This, I'm Outta Here!.
- October 7-8, 2002: In the second month of her tenure, Meredith got smitten by a contestant and quickly proceeded to make things...awkward.
- In one episode, a Phone-A-Friend responded "Meredith?" immediately after picking up the phone.
- During a 2007 Movie Week, a young contestant reached the $250,000 question, which just happened to be about one of his favorite movies. His reaction has been compared to "his [probable] o-face". He answers quickly. Meredith doesn't even bother to draw out the suspense.
- 2008: One contestant's eight-year-old daughter was also a big fan of the show, and viewers got to see one of her drawings of her mom and Meredith on-set. Meredith doesn't see the resemblance.
- May 2011: When a question about the planets came up, Accidental Innuendo (or was it a Freudian Slip?) was inevitable.
- September 2011, Celebrity Week: Freud was... mostly right.
- September 2012, Celebrity Week: Cheech Marin shows kindness and warmth to Meredith in his typical way, by presenting her with adult brownies.
- October 2012: Brandon Saunders gets a question about a Fan Nickname for a cable network due to its late-night offerings. It quickly escalated, leading to him using Ask the Audience. The climax? 69% said "Skinemax". Freud Was Right, indeed.
Cedric the Entertainer
- September 2, 2013: Unsurprisingly, Cedric delivered on his very first day, while discussing a question about hardware supplies with 18-year old contestant Nicholas.
- On at least two occasions, contestants had to sing songs to figure out the answer to a question; one involving guessing how many U.S. states have two words in their name, and, probably the funnier of the two, extrapolating how many times the word "Brady" is mentioned in the theme of The Brady Bunch.
(Nothing as of yet, but here just in case.)
- One contestant's Phone-A-Friend remained silent until saying "Hello?" at the 29th second.
- A Fastest Finger question asked "Starting with Stop, put the traffic light sequence in order according to the British Highway Code", the answer being red, red and amber, green, amber (C-B-D-A). Nobody got it right. Even funnier is what host Chris Tarrant said to the audience before revealing the correct order — "If any of them gets this question wrong, don't let them give you give a lift home."
- In a similar vein to the above, another Fastest Finger question asked for the correct order of words in the Jack and Jill nursery rhyme, being C (Jack and Jill went up a HILL) B (To fetch a bucket of WATER) D (Jack fell down and broke his CROWN) A (And Jill came TUMBLING after). No one got it. As he's reading out the answers, Chris ponders what he's doing with his life, and just like above, bursts into hysterics when it was revealed that no-one got it.
Chris: *laughing* Oh, I love it! So... settle down at home, it could be a long night! So Jack and Jill's a bit high level for you, so... what shall we do now, Teletubbies? What would you like?
- Ralf Schnoor's Phone-A-Friend, overlapping with Moment of Awesome. With a million euros on the line, he calls his friend and starts the 30 seconds with (roughly) "Hi. How are you?" and proceeds to chat casually for another five seconds. The look on host Günther Jauch's face was priceless.
- A glitch happens with display screen showing the questions and answers. The host's expression when this happens is hilarious.
- A few times it just so happened that the result of the "Ask the Audience" lifeline resulted in a 25% agreement for every single answer, which as usual resulted in funny facial expressions and snarky comments.