- Date unknown: A contestant picks the last clue on the board and gives a correct response. Alex says, "Correct. Select again." without realizing it. Cue the confused contestant saying, "I can't, the board's empty."
- 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 a man in his 80s deadpan his way through the likes of "Livin' la Vida Loca", "Hollaback Girl", and "I'm Too Sexy" with that Tidewater accent of his.
- 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 January 4, 2000, the champion Jack Archey had a locked-up win in his fifth game, 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.
- September 10, 1984: To say that the current version had a funny moment on the first episode, would be an understatement. Greg Hopkins, an energy demonstrator from Ohio, and the first winner on the show, with a total of $8,400, showed of such skills during the contestant interview. He took out a balloon to use as a Uranium atom, split it into two separate atoms, and flew them up in the air. Alex responded to this by saying "Greg, try and relax."
- September 20, 1984: A contestant rings in on the clue, "Number of blank tiles in a Scrabble set," and guesses 36, causing the audience to go wild. Alex tells him, "I'm glad you haven't been playing Scrabble, I'm glad you've been playing Jeopardy!"note
- November 21, 1985: During the first Tournament of Champions, Steve Rogitz accidentally reads the category "The U.N." as "The Un," causing the entire studio to laugh. Alex corrects him with mock anger and proceeds to read the clue while trying not to crack up.
- November 6, 1986: A funny answer that Trebek liked.
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.
- Mid-1980s: This "Mythology" clue.
Alex: He gave his name to a class of snakes.
Contestant: Who was Herpes?note
- November 19, 1986: An early example of Getting Crap Past the Radar was this clue: "We don't know if Lois ever complained about him being 'faster than a speeding bullet.'"note
- February 16, 1987: An answer that Alex seemed to agree with.
Alex: Ben Franklin said, "There was never a good war or a bad" 1 of these.
Contestant: What is a woman?
Alex: No, sorry. I like your thinking, though.note
- March 17, 1987: "Of 'Him', 'Her', 'You', & 'Me', the one never a top 40 hit." All three manage to ring in with the wrong three choices (Me, You, and Him, respectively).
- April 6, 1988: A contestant who admitted to not being comfortable with Audio Daily Doubles wagers $5 when he finds one but later wishes he had bet $10 when he immediately comes up with the correct response.
- November 2, 1988: Two moments.
: For an upper GI you drink this; for a lower GI... well, we won't talk about that. Eileen
: (rings in
) What's a barium enema? Alex
: (Beat, followed by uncomfortable gibberish
) Hmm. No, we can't give you that, I'm sorry. Alison
: (rings in
) What is barium? Alex
: Barium, yes. Uh, "For an upper GI, you drink" it. And uh, no matter how you— (all three contestants laugh
) —I don't even want to explain it.
- Later, no one gives a correct response to a clue concerning the lyrics to "Red River Valley":
Alex: "Come and sit by my side if you love me." Phil, then we can do other things, of course.
Phil: Right, not with you, thank you.
- July 1989: During the Seniors Tournament, Ouida Rellstab, the eventual winner, tells Alex in an interview segment that she raises turtles, but with her thick Louisiana accent, Alex mishears her saying she races turtles.
- March 30, 1990: This interesting response.
Alex: It can be a spokesman, part of your phone or a protective rubber device worn by a boxer.
Contestant: What is a cup?note
- 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.
There's a daily cash prize of $1,000 aaand fuck!
- Another (repeatedly deleted from YouTube) Phone Jeopardy! outtake reel ended with Alex saying "Tinker Bell" in a funny voice. When someone offstage reprimands him for the voice, he yells "Fuck 'em!"
- November 5, 1991: During the Tournament of Champions quarterfinal games, Teen Tournament winner Andy Westney gets stumped by this Daily Double.
Alex: On Dec. 4, 1783 George Washington bade his officers farewell at this New York City tavern.
Andy: What is the...Whiskey A Go-Go?note
- From Season 8 (1991-92), another one of Trebek's favorite answers.
Alex: George Bernard Shaw called this condition "the greatest of evils and the worst of crimes."
Contestant: What is marriage?note
- October 26, 1992: On the first ever Celebrity Jeopardy! game, Alex interrupts the Jeopardy! round after eight clues to ask Regis Philbin to jump in on the game since he hasn't gotten a chance to ring in yet. Regis holds up his signaling button and yells, "Is this thing working!?" Regis finally gets a correct response after the first commercial break, resulting in cheers from the audience.
- October 30, 1992: Ed Begley, Jr. picks the first three clues of "The Environment," with Rosie O'Donnell giving a correct response to the third. She tries another category but when Ed gets a correct response on that, he goes back to "The Environment." Rosie: "Damn you!"
- November 11, 1992: During Double Jeopardy in the Tournament of Champions quarterfinals, Teen Tournament winner April McManus discovers one of the Daily Doubles, but not feeling comfortable about the category (Historic Homes), wagers only $100, but gets it right to her surprise. So, she picks the next clue in Shakespeare, which is the other Daily Double, and feeling confident, wagers $1000, only to get it wrong.
- November 20, 1992: For the final game in the Tournament of Champions, finalists Jerome Vered, Leszek Pawlowicz, and Bruce Simmons laugh and shrug while their pitiful first day totals are announced ($700-$4000-$0, respectively) due to an anti-climatic ending in Final Jeopardy the day before.
- January 19, 1993: Air Force Lt. Col. Darryl Scott wins with a score of $1.
- May 14, 1993: When no one rings in on a clue concerning the subtitle of En Vogue's "My Lovin' (You're Never Gonna Get It)", Alex adds, "and you didn't get it."
- November 9, 1993: When Edward Asner fails to ring in on a clue before Pat Sajak.
I think my buzzer's not working. Alex:
My standard line in this kind of a situation is, "No, it's not the buzzer." Pat:
(amidst audience laughter
) Oh, jeez, the tension developing here!
- July 6, 1995: The answer: "Cape May, at the end of the Garden State Parkway in this state, is the USA's oldest seashore resort." The correct response, New Jersey, happens to be the home state of two of the contestants but the third player beats both of them to it.
- The Final Jeopardy answer is about the play The Seagull, but nobody gets it right, including champion Isaac Segal (sounds like "seagull")note . Alex lampshades this the next day.
- July 7, 1995: The answer: "The proceeds from some of her souvenir hatchets helped fund a home for wives of alcoholics."
Isaac: Who is Carrie Nation?
Alex: Carrie Nation, yes. But I like Robert's thought.
- November 6, 1995: This exchange on a celebrity episode:
Lynn Redgrave: Why am I minus? Tell me, give me a good reason! I've been answering, I've been beeping. These beastly people [David Duchovny and Stephen King] next to me are not helping. They don't say, "After you, Lynn," like real gentlemen. What's the matter?
Alex: Does the word, "stupid," mean anything?
- September 6, 1996: Similar to the example from Season 8.
Alex: "Elbert Hubbard defined this as 'a monotonous interval between fights.'"
Contestant: What is marriage? (The correct response is "peace.")
- April 1, 1997: For April Fool's Day, Pat Sajak replaces Alex as host of Jeopardy, with the first round categories derived from WoF.
- May 9, 1997: One particularly funny slip-up bordering on Getting Crap Past the Radar, from the International Tournament:
Alex: If a Japanese isha (doctor) asks you to stick out your shita, he means this.
Per-Gunnar Hillesoy: What is your...behind? note
- October 16, 1997: Johnny has just finished reading some promotional copy, and throws back to Alex. This exchange ensues:
Alex: Thank you, Johnner. (beat) Johnner? Johnny.
Alex: My tongue is not working today. However, let's see if I can get it to say what the Final Jeopardy! category is.
(the board reveals "Famous Pairs")
Alex: Famous Pores. We'll be back with the clue in a moment.
- 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 18, 1999: "Readings From Homer." Dan Castellaneta reading Homer in his Homer Simpson voice.
- January 13, 2000: A contestant during Double Jeopardy!
Lewis: Um, Nymph-O-Mania for $200.
Alex: No, no, it's 'Nymph-O-Rama' [audience loses it] note
- 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 6, 2000: A contestant who gets stumped by a Daily Double responds with, "Who are three people who have never been in my kitchen?"
- June 3, 2002: Four-time champ 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 rang in 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 year" 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.
Was it me, or was it the show? (Beat
) It was the show.
- November 8, 2002 (The last show to use the 1996-2002 set): After the time runs out for the Final Jeopardy! clue: "In the continental United States, this city is the southernmost state capital."
- September 26, 2003: "Tricky Questions" for $400 reads, "It's the technical reason you can't take a photograph of a man with a wooden leg." After no one gives the correct response, Alex says the correct response: it's because wooden legs can't take photographs. Cue loud groans from the audience, followed by Alex quipping "I just read 'em!"
- July 19, 2004: A video clue from Cheryl of the Clue Crew — "Introduced in 1990, it's the program I'm using [here] to create an unusual image." Cue her using Photoshop to put a mustache on an image of Alex.
Alex: Not so unusual.
- 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.
(clue: "This term for a long-handled gardening tool can also mean an immoral pleasure seeker."
) What's a hoe? Alex:
) No. (beat; laughs
) Whoa! Whoa! Whoa! They teach you that in school in Utah, huh?
(the correct answer was "Rake"
- 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?" note
- 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): During the final taping session of the Ultimate Tournament of Champions, Trebek walked out without pants on after hearing the final three contestants (one of whom was Ken) say that they had considered playing the game without pants themselves. As a camera behind the podiums showed, they still had their pants on.
- May 6, 2005: In Round 2 of the Ultimate Tournament of Champions, the Final Jeopardy answer: "The name of this character, introduced in 1894, is from the Hindi for 'bear'.note Jonathan Groff (no, not him) guesses "What is Pooh?", saying to Alex "At least I got to say 'What is Pooh?' on national television."
- September 14, 2005: Unable to come up with a correct Final Jeopardy! response, John writes "Who is Jimmy McGuire?", one of the members of the Clue Crew. When Alex questions him on it, John replies that he's getting back at Jimmy for getting his name wrong during a contestant search.
- November 10, 2005: The Final Jeopardy! category "Billboard Magazine" had this clue: "Launched in 2004, Billboard's first Top 20 chart for these included 'My Boo', the 'Halloween' theme & 'Ice Ice Baby.'" One contestant wrote down "What is the Worst Songs Ever?"note
- 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.
- January 4, 2006: Four-day champ Tom Cavanaugh's response to Final Jeopardy! - "What is I have no freaking clue?"
- November 6, 2006: A contestant writes "What is Homer?" for his response to the Final Jeopardy! clue: "John Dryden in 1683 was the first to use the term "biography"—appropriately, while writing about this Greek." When Alex says he is incorrect, he replies with, "D'oh!"note
- June 15, 2007: A losing contestant used "Who is Kebert Xela?" as his Final Jeopardy! response.
- September 13, 2007: Dave hits a Daily Double.
Boy, Alex, I've always wanted to say this - I'd like to solve the puzzle
(laughter; cut to Alex
Come here. Come here. You want a piece of me?
- Cue the Brick Joke when Dave hits the other Daily Double later in the round. After he wagers $5,000, Alex quips "that'll buy a lot of vowels."
- 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 Michelangelo?)
- 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 Simon Cowell, which the third contestant got right.)
- May 2, 2008: With two returning champ (due to a technical difficulty during the previous episode's Final Jeopardy!), the 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-champs and said "We heard from you yesterday."
- June 26, 2009: The categories for Double Jeopardy! are "My Bologna", "I Lost on Jeopardy!", "Like a Surgeon", "White & Nerdy", "Eat It", and "Weird 'Al'".
- 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 contestant 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 contestant fails the clue ("The past tense of a word meaning 'to strike', from The Bible"; he said "smat" instead of "smote"), which Trebek attributed 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 I got none right?"
- 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:
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.
- 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: ...and Oreo cookies are introduced.
Ken: What are the '20s?
Alex: No. Watson?
Watson: What is 1920s?
Alex: No. Ken said that.
- March 3, 2011: An epic Getting Crap Past the Radar exchange in the category "Starts with a Body Part":
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!
- 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 High Rollers set, audience laughter at Alex's ad-lib, then groans when nobody rings in.
- One 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.
- July 8, 2011: Twelve-year old Maddie Harrington rings in with an incorrect response to a clue and mumbles, "Crap!" loud enough for Alex to hear. He quips, "Yeah, I get upset too, Maddie. Believe me. Same reaction."
- November 3, 2011: "Kara has obviously had much more experience than I."
- November 4, 2011: Early in a Tournament of Champions, after two rounds of being curb-stomped by Joon Pahk, all John Krizel could write down for Final Jeopardy! was "What is I have no idea?"...while 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 2, 2012: After nobody rings in on the final answer of Jeopardy! Round, Alex unknowingly says "Pick again," leading to this:
Judge: (off-screen) We're out...
Alex: Oh, we're out? Okay.
Contestant: I'll go more Super Bowl questionsnote .
(audience laughs harder)
Alex: You want more Super Bowl clues? All right. (audience continues laughing) We'll take a break. We'll come back to start Double Jeopardy! after this. It went too fast.
- 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 Daily Double 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: From a 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." $5 has been the minimum wager since 1964.
- 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 nobody else gets a chance to ring in, followed by Alex quipping "This is a family show!" note
- July 12, 2012: Alex interviews a contestant who said that she once had a pygmy goat who met his demise by eating a bag of Quikcrete, which got the audience laughing. Alex asked whether it was a 60 or 80 pound bag. She replied sarcastically, "You're being insensitive!" Cue Alex cracking up and declining to interview the champion, saying "I don't wanna talk to you!"
- July 13, 2012: Alex has too much fun using a bullhorn to deliver a clue.
- October 2, 2012: Final Jeopardy! is "OED's earliest citation of this 5-word phrase is 'Now, Monsieur Poirot, you would without doubt like to visit' this place." Contestant Daniel's response? "What is the bathroom?"
- November 2, 2012: After giving a correct response of "What is love?", Paul Nelson sneaks in "baby, don't hurt me."
- December 7, 2012: Alex tries Nelson Muntz's "Haw haw!" and fails spectacularly.
- December 11, 2012: A Daily Double asks what profession St. Andrew is the patron saint of. The contestant, clueless about the subject, jokingly said golfing (the correct answer is fisherman).
- The June 13, 2013 episode made this joke an Ascended Meme with the clue "No word on his putting skills, but he is the patron saint of Scotland." during Double Jeopardy.
- February 6, 2013: The categories for the Jeopardy! round are "Hey, I Just Met You", "This Is Crazy", "But Here's My Number", "So Call Me", "May "B"", and "Yeah, We Went There".
- February 12, 2013: After an incredibly gutsy Daily Double, Leonard Cooper is leading going into Final Jeopardy! at the end of the Teen Tournament. The clue: "On June 6, 1994, he said, 'The eyes of the world are upon you.'" Leonard wrote down "Who is some guy in Normandy? But I just won $75,000!"
- February 21, 2013: A contestant in the Tournament of Champions, who had previously called Trebek "the Devil" on account of his tempting her to risk everything on a Daily Double, announced that she brought him a pitchfork "in case you don't have one already." Cue humorous Aside Glance from Trebek.
- February 25, 2013: Clue has something to do with cheese. Colby answers. Alex: "also a Colby cheese!" Colby: "Never heard that before, Alex!"
- March 7, 2013: A category about horse coat colors includes a question about the "'strawberry' type of this horse". A contestant guesses "strawberry blonde?" (Try roan.)
- April 29, 2013: "The Sexiest Potpurri Ever" was in the Jeopardy! round. It had Alex talking in a very suggestive tone as he read the clues, while soft porny music was played in the background of each clue.
- May 14, 2013: Contestant is talking about James Bond, and mentions that her favorite is Sean Connery. Alex: "I don't like Sean, for reasons that should be obvious to many of you who watch television on Saturday nights."
- September 2013: The promo for the show's "Battle of the Decades", with Alex's 1980s, 1990s, and current selves. Among the many fun moments:
- October 2013: Alex shows up in a holiday-themed safety video for Delta Airlines. At the end, the presenter says, "As we come through the cabin for our final safety check, please let us know if you have any questions." Cut to Alex sitting in a business class seat with a newspaper in his hand while a flight attendant approaches the passenger sitting behind him:
Flight attendant: This is a traditional milk-based holiday drink.
Alex: [dryly] What is eggnog?
Flight attendant: Correct!
- November 28, 2013: "Show Biz Stupid Answers" for $200:
Alex: Julie Chen & Sara Gilbert give their view as 2 of the co-hosts of this talk show. (Whitney rings in) Whitney?
Whitney: What is The View?
Alex: No. (John rings in) John?
John: Uh... I will also say, what is The View? (all three contestants and Alex laugh) 'Cause that was my answer!
(beep beep beep)
Alex: No, it's called The Talk.
- December 18, 2013: Craig answers a question regarding The Dark Knight Rises by doing his best Bane impression.
- January 6, 2014: Alex Trebek raps (well, tries to anyway)
- January 13, 2014: "What Are You Afraid Of?" for $1000. It's a Daily Double, and the contestant is asked to name what "Selenophobia" is the fear of. She doesn't know, so she guesses, "What is the fear of Mexican music stars?" (The correct answer was the Moon)
- January 31, 2014: Two categories in the Jeopardy! round are "I Have the Wine" and "By Johnny Cash", in reference to a hilarious missolve on Wheel of Fortune about a year prior.
- February 21, 2014: Johnny Gilbert deadpanned another set of song lyrics. It never fails to please, but this time around, Alex predicted that Johnny would become a Twitter sensation. Cut to a very amused and flattered Johnny.
- April 4, 2014: On the Friday episode of the 2000s "Battle of the Decades" week...
- Maria Weglinsky sees that "Celebrity Reality TV" is the last category, and says "Do I have to?" before selecting a clue from it. A couple clues later, opponent Dan Pawson rings in on a clue about the Kardashians and prefaces his response with "Do I have to?"
- Final Jeopardy! category: 20th Century Literature. Clue: "'It was one of those pictures... so contrived that the eyes follow you.... Beneath' the picture was this 5-word quote." Pawson's response: "What is 'Don't get undressed near here?'" (Correct response: "What is 'Big Brother is watching you?'")
- May 14, 2014: Before the third semifinal of the Battle of the Decades, with Ken Jennings and Brad Rutter having already advanced to the finals, Alex makes an opening prediction: The third finalist would not be IBM's Watson.
- September 29, 2014: In an unaired outtake, Alex interviews contestant Alisa, whom he accidentally calls "Catherine" because he is looking at the wrong card. He prompts Alisa about spending a night in the Tower of London (a fact from Catherine's card), after which Alisa makes up on the spot a story about paying off a beefeater. Upon realizing his mistake, Alex walks off-set, no doubt mentally Face Palms, and explains to the audience:
Alex: You were asking, uh, how much of the material I know? I don't even know where the hell I am today. Uh, Catherine what you should've said was, "Isn't that interesting? Alisa slept in the Tower of London too! Damn!"… That's never happened before.
- December 9, 2014: "What's Killing You?" for $600. The category is about lethal weapons.
Ann: (rings in) What is a robot?
Alex: Be more specific.
Ann: A robot that turns into things that kill you?
Ann: An Autobot?
- The second contestant to ring in gives the correct response of Decepticon