[[folder:In General...]]
* 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.

[[folder:Regis Philbin]]
* 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]](this was back when the two choices eliminated by the 50:50 were ''not'' random but pre-selected by the writers, usually as the two choices the player was most likely to eliminate as incorrect)[[/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 [[http://www.youtube.com/watch?v=VDkJCvUIhoY&t=1m45s 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.
* On another ''Celebrity'' episode, Jon Stewart was playing for an Alzheimer's Association of America, which led to this CrossesTheLineTwice 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.
* 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 [[http://www.youtube.com/watch?v=dDci8SdemOo&t=2m50s as if it was worth $20,000,000]], and HilarityEnsued.
-->'''Regis:''' Here we go for $20,000,000! [[spoiler:(''catches his mistake'') A 20--?! I'm sorry! (''audience cheers'') Noooo, I take it back! "Rich jumped up!" "Really?!" Twenty ''thousand'' dollars...]]
* An early contestant named Tom Coletta had [[http://www.movieweb.com/tv/TEu3hCwvyXzQyw/im-a-fat-man-regis-my-heart-cant-take-this 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 [[AccidentalInnuendo suggestive]] [[http://www.youtube.com/watch?v=lGKxQurtJqw it sounded at first.]]
* Also from the 10th-Anniversary Specials, [[https://www.youtube.com/watch?v=YtrZ4Dec6eo 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!"
** In the same game, Denis Leary got a question about which book contained a chapter named "I Am Born" (correct answer is ''Literature/DavidCopperfield''), and one of the choices was ''Literature/{{Frankenstein}}''. Denis said he never read ''Frankenstein'', but said he saw ''Film/YoungFrankenstein''. Regis added that he liked it too, and mentioned Gene Hackman.
--> '''Denis''': ...Gene ''Hackman''?? Gene ''Wilder''.\\
'''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!

[[folder:Meredith Vieira]]
* October 2, 2002: Minda Lopez takes [[http://www.youtube.com/watch?v=FqK4YhY_WsA 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 ScrewThisImOuttaHere.
* October 7-8, 2002: In the second month of her tenure, Meredith got [[http://www.youtube.com/watch?v=f9o9mwGIbN8 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 [[http://www.youtube.com/watch?v=5monB4fIzy8 the $250,000 question]], which just happened to be about [[OfficeSpace one of his favorite movies]]. His reaction has been compared to [[TheImmodestOrgasm "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 [[http://www.youtube.com/watch?v=yTnV56p3Hro one of her drawings of her mom and Meredith on-set.]] Meredith doesn't see the resemblance.
* May 2011: [[http://www.youtube.com/watch?v=zEZ0DttCS9s When a question about the planets came up]], AccidentalInnuendo (or was it a FreudianSlip?) was inevitable.
* September 2011, Celebrity Week: [[FreudWasRight Freud was...]] [[http://www.youtube.com/watch?v=_5I3jzbFE7c 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 [[http://www.youtube.com/watch?v=Bmf99tyUd40 question]] about a FanNickname for a cable network due to its late-night offerings. It quickly escalated, leading to him using Ask the Audience. The [[IncrediblyLamePun climax]]? 69% said "Skinemax". FreudWasRight, indeed.

[[folder: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.
-->'''Nicholas:''' I don't know what a caulk gun is. (''audience laughs'')\\
'''Cedric:''' Trust me, by the time you get to college, [[YouWillKnowWhatToDo you'll know]] [[ICallHimMrHappy what it is]]! (''audience laughs harder'')
* 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 ''Series/TheBradyBunch''.

[[folder:British Version]]
* One contestant's Phone-A-Friend [[http://www.youtube.com/watch?v=jRLnTMYDS-A 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). [[http://www.youtube.com/watch?v=yTGX_4u90dg 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 drive you home."

[[folder:German Version]]
* [[http://www.youtube.com/watch?v=eXTSUZtMhCs Ralf Schnoor's Phone-A-Friend]], overlapping with MomentOfAwesome. 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.
* [[http://www.youtube.com/watch?v=079oaxtjFBk A glitch happens with display screen showing the questions and answers.]] The host's expression when this happens is hilarious.

[[folder:Australian Version]]
* On the [[CelebrityEdition Battle of the]] [[GameShowHost Game Show Hosts]] [[CelebrityEdition edition]] of "Millionaire", [[ThePriceIsRight Ian Turpie]] [[https://www.youtube.com/watch?v=Cx84h6fiZPg phones his brother, Keith]], [[SarcasmMode who turns out to be really helpful]].