Who Wants to Be a Millionaire?/Funny

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.

Regis Philbin

During one of the Celebrity Millionaire episodes, 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 ^[1]...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.
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...

A contestant in the 10th Anniversary Special almost lost on her first question because of how suggestive the question sounded at first.

Meredith Vieira

October 7–8, 2002: In the second month of her tenure, Meredith got smitten by a contestant and quickly proceeded to make things...awkward.
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.

British Version

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 drive you home."

German Version

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.

↑ (this was back when the two choices eliminated by the 50:50 were not random, but were pre-selected by the writers, usually as the two choices the player was most likely to eliminate as incorrect)

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[1] (this was back when the two choices eliminated by the 50:50 were not random, but were pre-selected by the writers, usually as the two choices the player was most likely to eliminate as incorrect)