Jeopardy!/Funny

"Alex Trebek: These are the biggest examples of humor that the members of All The Tropes could find on Jeopardy! You: What are Crowning Moments Of Funny? Alex: (looks off-camera) ...Crowning Moments Of Funny or Funny Moments, yes. Go again."

In General...

 * Any time calling a category forms a funny sentence, such as "Let's go to Hell for $400, Alex".
 * Any time a contestant exploited the show's "credit so long as it's phrased in the form of a question" rule, such as Ken Jennings' "What be Ebonics?" (September 16, 2004).
 * At some point, while "Who are The Who?" might have been the more properly-formed answer for a given question, someone answered with simply "Who?" and got credit.
 * Any time sweeping a pop culture category causes Alex to comment that contestants are wasting their lives.

Art Fleming (1964-75, 1978-79)
"(Audio Daily Double: NBC "In Living Color" music sting plays) Gene: Well, it ain't an eye! That would be the very famous NBC Peacock.
 * Circa 1972: Gene Shalit tackled a Daily Double in a...unique way.

Art: Question.

Gene: Has anybody around here seen the very famous NBC Peacock?"

"2,000-Year-Old Man: Two thousand years ago, we had this show. We had Jeopardy! Art: You had Jeopardy! two thousand years ago?! 2,000-Year-Old Man: Well, it wasn't this hippy-dappy-happy game you've got here."
 * February 21, 1972: To celebrate the 2,000th show, Mel Brooks appeared as (rather aptly) the 2,000-Year-Old Man.

Alex Trebek (1984-Present)
"Alex: By the 4th century A.D., Rome had 28 public ones stacked with rolls of papyrus. Gary: What are public toilets? Alex: No, sorry. Harvey: What are libraries? Alex: Yes, but I kinda like Gary's answer for humor."
 * In general, any category where announcer Johnny Gilbert reads off lines from a work (usually songs) in a deliberate tone. Examples include Johnny Gilbert Does Shakespeare (January 13, 1999, with a rare Daily Double on the top row), Johnny Gilbert Rocks (November 29, 1999), and Johnny Gilbert Raps & Rocks On (October 7, 2008). You haven't lived until you've heard Johnny deadpan his way through "Livin' la Vida Loca".
 * From the show's debut on March 30, 1964 through July 18, 2003, a player could only win five times before they were forced to withdraw. On the episode airing January 4, 2000, one four-time winner had a locked-up win on his last appearance, so for Final Jeopardy! he wrote as his response "What is Woo Hoo Yee Haw Yeah Baby". Alex read the answer in a deadpan tone, with a "WTF?" face the whole time.
 * November 6, 1986: A funny answer that Trebek liked.

"Alex: There's a daily cash prize of $1,000 aaand fuck!"
 * June 18, 1990: This montage of Trebek swearing like a sailor and drinking what appears to be alcohol (but is actually Diet Coke and a glass of water) while trying to shoot some Phone Jeopardy! promos.

"Alex: If a Japanese isha (doctor) asks you to stick out your shita, he means this. Contestant: What is... your behind?"
 * January 19, 1993: Air Force Lt. Col. Darryl Scott wins with a score of $1.
 * May 9, 1997: One particularly funny slip-up bordering on Getting Crap Past the Radar, from the International Tournament:

"Alex: Was it me, or was it the show? (Beat) It was the show."
 * February 13, 1998: The Tournament Of Champions finals included professional humorist Bob Harris. Starting the second heat of the Finals with $0 because he missed the previous day's Final Jeopardy!, Harris was a source of Snark Bait for the rest of the show — including at the very start, when Trebek tried to suggest a possible comeback and Harris replied "I don't need your pity!" Trebek countered by stating that while the other two players would have their scores from the day before cleared, Harris was already at $0 so they didn't need to clear his. "So much for pity."
 * January 13, 2000: A contestant during Double Jeopardy! selected "Nymph-O-Mania for $200". Alex corrected him, saying "No, no, it's NYMPH-O-RAMA."
 * May 16, 2000: During the Tournament Of Champions, famous blind contestant Eddie Timanus responded "What are suckers?" to an answer of "P.T. Barnum's victims (7 letters)". The way he said it drew a ton of laughs from the audience, and Alex replied with "You didn't have to say it like that!"
 * June 3, 2002: Four-time champion Jill Bunzendahl Chimka said that if she won five games, she'd give the car she won to her son, Cory. When she didn't know the answer to Final Jeopardy!, she wrote "What is Sorry Cory, No Jag?"
 * June 28, 2002: After nobody gave a correct response to a clue asking for the first game show Trebek hosted in the U.S., he lampshaded the show's obscurity by saying "...and that's why it only lasted for one season" before stating that the correct response was The Wizard of Oz. When they came back from commercial, he corrected himself and said that it was actually titled The Wizard of Odds.

"Alex: Not so unusual."
 * July 19, 2004: A video clue from Cheryl of the Clue Crew: "Introduced in 1990, it's the program I'm using to create an unusual image." Cue her using Photoshop to put a mustache on an image of Trebek.

"(clue: "This term for a long-handled gardening tool can also mean an immoral pleasure seeker.") Ken Jennings: (rings in) What's a hoe? Alex (automatically): No. (Beat; laughs) Whoa! Whoa! Whoa! They teach you that in school in Utah, huh? (the correct answer was "Rake")"
 * October 8, 2004: A Ken Jennings one, made so by the particular colloquialism he and Alex Lampshade. What makes the moment even more funny is that it takes Alex a split-second to catch up to Ken's wisecrack.

"Contestant (about an Algerian mother-in-law): She was excited that I was going to be on Jeopardy! We had to explain it to her, though, they don't have Jeopardy! in Algeria. Alex: Well, they probably do, but the stakes are much higher. (audience laughter; Alex looks into camera) I'm probably going to get mail for that one."
 * October 6, 2004: Another one from Ken. The Final Jeopardy! category was 2004, and the clue was "On Monday, December 13, 3 people designated these will meet in Cheyenne, Wyoming to help decide the world's future." Ken wrote "What are the Three Stooges?"
 * November 10, 2004: In the College Tournament, computer science major Kermin Fleming wagers $1,337 in Final Jeopardy! and wins. He then goes on to explain his wager later. (He eventually won the tournament.)
 * May 2005 (unaired): Near the end of the Ultimate Tournament Of Champions, Trebek walked out without pants on after hearing the contestants (one of whom was Ken) say that they had considered playing the game without pants themselves. As a camera behind the podiums showed,.
 * November 14, 2005: Alex deadpanned rap lyrics in a category called "MC Trebek in da Hizzouse". Four years later, somebody made a beat mix of it.
 * June 15, 2007: A losing contestant used "Who is Kebert Xela?" as his Final Jeopardy! response.
 * September 13, 2007: A contestant hits a Daily Double and says, "I've always wanted to say this — I'd like to solve the puzzle." Alex laughed and jokingly said, "Come on over here. You want a piece of me?"
 * October 25, 2007: The Final Jeopardy! clue read "Paul III roared at him, 'I have waited 30 years for your services. Now I'm Pope, can't I satisfy my desire?'" One contestant responded "Lady Godiva". Alex cracked up and remarked that he'd give it to him just for the humor! (Correct response: Who is ?)
 * December 17, 2007: The returning champ gives a wrong response in the Most Populous Nation category, followed by the second contestant ringing-in to give the correct one. Four times in a row. You can hear the audience beginning to crack up by the third time this happens.
 * January 28, 2008: The Final Jeopardy! clue was "Not an actor, he is the highest-paid foreign-born personality on the 2007 Forbes list of top television earners." Two of the contestants wrote down "Who is Trebek?" as their answers, to which Trebek laughed and said, "I wish!" (The correct answer was, which the third contestant got right.)
 * May 2, 2008: With two returning champions (due to a technical difficulty during the previous episode's Final Jeopardy!), the only new contestant told a very long story with Alex getting noticeably less and less interested as she rambled on. When she finished, Trebek turned to the co-champions and said "We heard from you yesterday."
 * October 15, 2009: Kareem Abdul-Jabbar got his own line from Airplane! wrong on a celebrity game.
 * April 7, 2010: Upon getting a Daily Double, one of the contestants said "I've always wanted to say this, Alex — I'd like to buy a vowel. Err, I'd like to make it a True Daily Double." Cue the Death Glare from Trebek. Then the clue: "The past tense of a word meaning 'to strike', from The Bible", which the contestant fails (he said "smat" instead of "smote"). Trebek attributed this to divine retribution.
 * April 16, 2010: The semifinal of Celebrity Jeopardy! had Jane Curtin and Isaac Mizrahi trading hilarious quip after quip.
 * May 21, 2010: Stefan Goodreau, a finalist in the Tournament Of Champions, had not given a single correct response in Final Jeopardy! during the Tournament. His response for the last clue of the Tournament? "What is ?"
 * Stefan was also the reigning champ in the "Liederkranz" episode, and still won despite an insane bet of $20,065 (from his $22,800). His opponents each finished Double Jeopardy! with $200.
 * June 23, 2010: The category "Alex Trebek Meets Auto-Tune", which had him sing five traditional songs via said Auto-Tune. A few days later, Jimmy Kimmel made fun of it.
 * December 16, 2010: "I'll take 'Your Momma' for $400, Alex."
 * One episode had this exchange:

"Alex: ...and Oreo cookies are introduced. Ken: What are the '20s? Alex: No. Watson? Watson: What is 1920s? Alex: No. Ken said that."
 * February 14-16, 2011: Watson's appearance on the show (against Ken Jennings and Brad Rutter, the show's two biggest winners) was about research more than anything, but he still managed to generate a couple:

"Alex: What are you going to wager? Watson: I'll wager six thousand, four hundred, thirty-five dollars. (audience laughs) Alex: ... I won't ask. (audience laughs harder) I won't ask."
 * Watson got lucky with the Daily Double, getting them both in Double Jeopardy. His logic in wagering was...odd, to say the least.

"(Category: US Cities; Clue: "Its largest airport is named for a World War II hero; its second largest for a World War II battle." ) Watson (response): "What is Toronto????" (audience mumbles in shock) Alex: What is Toronto, with a lot of question marks, which means, of course, that Watson had many many doubts. And the wager, how much are you gonna lose? (Watson's wager appears — a mere $947, causing the audience to laugh) Oh, you sneak!"
 * Similar to the above, Watson provided a double whammy of funny when he not only gave the wrong answer in Final Jeopardy, but had wagered an extremely small amount of money in an odd figure:

"Alex: The fur of this rodent, seen here, is said to be 30 times softer than human hair. Contestant: What is a titmouse? (looks offstage and laughs) I'm sorry!"
 * At the end of the IBM Challenge, Watson took the lead once again all the way into Final Jeopardy. When Ken Jennings revealed his answer, he wrote an extra side note in parentheses that got the audience laughing — "I, for one, welcome our new computer overlords."
 * March 3, 2011: An epic Getting Crap Past the Radar exchange in the category "Starts with a Body Part":


 * June 15, 2011: "Ruta Lee and Elaine Stewart rolled the giant dice on this game show. Whatever happened to that debonair fellow?" Cue pic of Trebek on the set, audience laughter at Alex's ad-lib, then groans when nobody rings in.
 * One recent contestant wagered an even amount plus $20 on the Daily Double. Alex asked why, to which the player responded that he had lost $20 during the trip to California and promised his wife that he would get it back during the game. He lost the Daily Double, but going into Final Jeopardy! had the correct response with a wager of...$20.
 * November 3, 2011: "Kara has obviously had much more experience than I."
 * November 4, 2011: For Final Jeopardy! after two rounds of being curb-stomped by Joon Pahk, all John Krizel could write down was "What is I have no idea?" and Tom Kunzen's answer consisted of just a rage face (and he even made a strip about it!). (Joon, of course, gave the right answer.)
 * January 16, 2012: One question in the category "Punch" dealt with the name of the animal used in the name of a punch to the back of the neck. The correct answer was a "Rabbit" punch, but the first contestant answered..."Donkey".
 * February 21, 2012: Unable to come up with the correct response on a clue regarding an act of Congress, the contestant says, "What is the I Just Lost $3,000 Act?"
 * February 22, 2012: One category involved Johnny Gilbert reciting famous phrases beginning with "This is…", all in the style of the show's iconic "This… is… Jeopardy!" intro. Of course, one of them was "This! IS! SPARTA!"
 * February 28, 2012: Contestant: "You better check yourself before you Trebek yourself."
 * March 7, 2012: A category is "lyrics of the artist," so we get to hear Alex read Umbrella and Sexy Back.
 * March 14, 2012: Contestant hits a Daily Double. Since he has less than the maximum value of a clue ($2,000), Alex lets him know that he can wager up to that amount. His response? "Well, in case I never get the chance, let's go $2,000." Later, another contestant uncovers the other Daily Double and says, "Just in case I don't get a chance to say this— $5." (the least amount one can wager)
 * March 26, 2012: A contestant plays the Think! music by manualism (making farting noises with one's hands).
 * April 3, 2012: The first two interviews. Joey says that he was in a rock band whose name he "can't even say on television", and that the "holes we cut strategically in our pants" ensured that the band only lasted one day. Then Tamara says that while in high school, she would sometimes dress as the school's panther mascot: "One of the seniors noticed, 'oh my God, she has boobs!' and yelled it to everyone…" (Insert Furry Fandom joke of your choice here.)
 * April 17, 2012: After a Clue Crew clue involving an inflatable shark, said shark makes a surprise appearance.
 * May 11, 2012: Finals of the Teen Tournament: One of the contestants answers "Who is Bella" with NOTICABLE disdain in her voice.
 * May 15, 2012: Kareem Abdul-Jabbar strikes again: "The 5 movie ratings in the U.S. are NC-17, R, PG, PG-13 & this one." "What is X?" Cue so much audience laughter that no one else gets a chance to ring in, followed by Alex quipping "This is a family show!"

Bob Bergen (GSN, 1998-99)

 * (Nothing as of yet, but here just in case.)

Jeff Probst (VH-1, 1998-2001)

 * (Nothing as of yet, but here just in case.)