Funny / Pointless

• Normally when a pair wins the jackpot, it's normally just a hug and Alexander coming over. Some reactions, however, go a bit more on the "absolutely hilarious" side:
  • Series 4, Episode 6: Contestants Paul and Tom win the jackpot. Paul then proceeds to kiss his own flatmate.
  • Series 5, Episode 38: Nick and Charlie show a bit too much brotherly love. They actually fist-bump each other, for crying out loud!
  • Series 5, Episode 45: Easily the wildest celebration (maybe ever on the show) is none other than Matt's. He and his dad Gwyn won the £7,500 jackpot, and Matt goes around... running around the set screaming and getting all over-excited. He even tries to hug Richard - but he gets friend-zoned out of it.
  WE GOT IT MATE, WE GOT IT!
• In a series 6 episode, the opening round category was novels by three-named authors. One pair had no idea whatsoever and decided to say American Psycho was written by Antony Worrall Thompson.
  Alexander: There is your red line. If Antony Worrall Thompson gets you below that, I will eat the column.
  • In the next episode there's a Continuity Nod where the same contestant got a right answer after a long lead-up of consideration, and Alexander quips "For a moment there I thought you were going to say Antony Worrall Thompson again".
• Speaking of Antony Worrall Thompson, on a celebrity special he ended up scoring 100 with a CORRECT ANSWER (with Honey, I Shrunk the Kids). Everybody in the studio broke up laughing, and Alexander couldn't recall ever seeing it happen before. Richard commented that one of the other teams in that game had just set the record for the highest single-round score that didn't include a wrong answer, only for Antony and his partner to break it again (189 vs. 183). The fact that there's even a music cue (and light show) for this very situation just makes it all the more hilarious.
• The contestant who got through the first round on both of his consecutive appearances with the same answer ("Malta").
• While discussing Queen Victoria, it's mentioned her first name was actually "Alexandrina"...
  Alexander: Like a female Alexander.
  Richard: You were known as "Victoria" for a while in The '90s weren't you?
  Alexander: ...My friends still call me that.
  Richard: The word you're thinking of is "clients".
• One Head to Head Question was "Things That Rick Astley Is 'Never Gonna' Do..."
• In one of the celebrity editions, one of the pairs of celebrities is the Chuckle Brothers. Richard takes the opportunity every round to complain that they haven't been knighted yet. Except when the round was French-themed...when he instead complained that they hadn't been given a Legion d'Honneur.
• January 5, 2012 - What could be classified as the strangest head-to-head round on the show at the time, either Nick and Charlie or Patrick and Chris are making it to the final and have reached one portion each.
  • Their third head-to-head question is about actors in Reservoir Dogs. Needless to say, Charlie is the only one of the four contestants who saw the movie and even he didn't remember it. He guesses Jimmy Nail for his team, while the other pair guesses John Travolta. They are both incorrect.
  Richard: I think you might be the only people to get Auf Wiedersehen, Pet and Reservoir Dogs mixed up!
  Nick and Charlie: (spoken together) Somebody has to!
  • After that, the question is now "Capital Cities of South America", which seems like a piece of cake but it just gets even stranger. Chris (who outright said before answering that he knows a lot about geography) ends up coming up with "Paraninebo", a complete botch-job of "Paramaribo", the capital city of Suriname. Needless to say, Nick and Charlie's answer completely lampshades the other team's mistake:
  Nick: Well, I won't lie. That's exactly what I was gonna go for, except I don't know how spelling errors and pronunciation errors go into it because I'm pretty sure that's not quite right. So can I say the same one?
  Richard: Uh, if it is substantially different, yep...
  Nick: Okay, I believe the capital city of Suriname is "Paramaribo". (Patrick and Chris look in shock, audience chatters quietly) Having lived in South America for eighteen months, can you give me the benefit of the doubt? (audience laughs quietly, Patrick shakes his head in embarrassment)
  Alexander: "Paraninebo" and "Paramaribo"...
  Chris: I just never heard it be- spoken before, I didn't know.
  Patrick: This is pronunciation, isn't it?
  Richard: Well, I would say spelled differently as well.
  Chris: "Spelled differently as well", okay...
  • Needless to say, the misspoken variant was obviously incorrect, and this cost Chris and Patrick out of the game, while Nick and Charlie would go on to win the jackpot (as mentioned above).
• The 300th episode began with Richard and Alexander exchanging gifts. Richard got Alexander a framed map of the Central African Republic, while Alexander got Richard a power cord for his laptop, which had apparently been running off battery power since the show premiered.^note The laptop is actually a non-functioning prop. Whenever Richard has to read something, it's always through a piece of paper.
• The category is "weddings". The teams are presented with a list of six famous women and have to name the famous men they married. Unable to identify any of them, one contestant picks Anne Hathaway and gives his answer... "Man Hathaway".
• The couple on the 6 February 2013 show who reached the final and were given the topic "Inspector Morse and Jack Frost novels". Unable to name any, they made up three on the spot and then made an extended charade of being certain that these were good answers.
• In an episode with the question being about British MPs named David, Nick or Ed (the names of the then leaders of the three largest political parties ^note David Cameron, the Conservative leader and Prime Minster; Nick Clegg, the Lib Dem leader; Ed Miliband, Labour leader and Leader of the Opposition), one contestant admitted she had no idea and picked an answer by taking one of the names and a colour. Her answer - Nick Brown - was Pointless.
  • Making this more incredible was Richard's revelation that Nick Brown was the only possible correct answer that could be produced by mashing together one of the names and a colour.
    • This veered into Awesome when the pair went on to win the Pointless Jackpot for £12,750.
• In the episode on 19th February 2013, a question was "Actors in the Magnificent Seven or Dirty Dozen films". One contestant, not knowing any, suggested James Brown. Alexander naturally started making jokes about the idea of the singer being in the film, but not only was the answer correct, but pointless. Turns out that American football player Jim Brown (full name James Nathaniel Brown) was in the Dirty Dozen. The contestant responded by bowing several times towards the audience, as Alexander asked Richard for the explanation with incredulity.
• Episode on 3rd April 2013 - the round was "Words ending in '..ind'". At the end of the round Richard went through the pointless answers as he does, then asked Alexander what he would have gone for. He said... befriend. A few moments later Richard points out what he's said, and Alexander wanders around the stage for a few minutes in embarrassment. Remember that Alexander Armstrong is an English graduate. Made even funnier by one of the contestants at the beginning of the next round, a retired primary school teacher teacher, giving him a mnemonic to remember how to spell it.
  Richard: You had the whole round to think of that.
  Richard: Don't worry [losing contestant], it could have been worse. [To Alexander] We should keep [contestant] and send you off.
• April 19, 2013, and some lightning-fast repartee from a pair of PE teachers.
  Alexander: "It appears you know more about monarchs attending the Queen's Jubilee than you do about Shakespeare."
  Contestant: "We were on the door."
  Alexander: "Oh, so it was you who didn't let Oman in?"
  Contestant: "He was wearing trainers."
• June 21, 2013; the category is "assassinated people". When prompted the clue "Assassinated by Lee Harvey Oswald in Dallas", one contestant replied "JR", sending Richard in tears and causing Alexander to fall over laughing. It didn't exactly help that the other contestant in the pair subsequently answered Joan of Arc for "French Revolutionary Stabbed in the Bath by Charlotte Corday".^note For the record, the correct answer to that one is Jean-Paul Marat.
• In one of the celebrity specials Ravi Bopara is trying to think of a Brad Pitt film from the 21st century, and his team-mate Phil Vickery suggests "Brad Pitt Does Christmas", which Ravi refines for his answer "Brad Pitt Does Halloween". This is mocked more than once in the rest of the show.
  Richard [after Legends of the Fall has not been accepted as another contestant's correct answer]: "Yeah, the full title is 'Brad Pitt Does Legends of the Fall'."
• A series 9 episode had the category "Words ending in -air". The first answer given, "unimpair" was wrong, prompting Alexander to reflexively say that it was so unfair. He realised at the last moment that unfair would be an answer, so he quickly swapped to "unjust", but took several seconds to recover from the laughter brought on by his near-miss.
• A pair of personable young female contestants reached the jackpot round and were given the categories "Solo Spice Girl Albums", "Children of Spice Girls" and "Actors in Spice World". When their minute's discussion time was up, one told Xander, "We're going to give you three children." She might have got away with it had she not immediately realised what she'd just said, leading to general hilarity. And trust Richard to top it...
  Richard: "Is that each?"
• In one January 2015 episode, the category "Capital cities in their native languages" came up, prompting one puzzled contestant to remark, "It all looks like it's written in another language". The audience was promptly in hysterics (and so was the contestant herself, once she realized the gaffe).
  Alexander: To be fair, it is written in several different languages.
• The contestant who, faced with the category of "famous guitarists", suggested "Lenny Hendrix".
• Round 2 of the episode broadcast on 26 October 2015, when the subject was songs with "wish" in the title, and all three teams joined the 300 Club - wrong answers from everybody on both passes and the tiebreaker. They were that awful. One team guessed that Val Doonican had a hit with "Wishing on a Star" in 1978...after Xander had already told them the singer was female. (They redeemed themselves on an emergency tiebreaker question about composers, with every team scoring 7 or less in a single pass.)
• One infamous moment in a January 2017 episode occurred when the subject of "Countries with names ending in two consonants" came up. One contestant reportedly had a mind blank and guessed Paris, leading to an astonished audience and her partner shooting her an icy Death Glare. It was not a right answer.
  • To make matters even worse, the contestant stated they were a honor Geography A-Level student.
• On a celebrities edition, in the final Barry Cryer gives Nyasaland as a country beginning or ending with N, which turns out to be incorrect as Nyasaland had changed its name to Malawi ...in 1964.
  Richard: Which, to be fair, is only 52 years ago, so we're all getting used to it.
  Barry: No wonder my letters never arrive!
• Another celeb edition kept it simple with the category name “Famous Dicks”.
  Richard: I don't know what you’re all laughing at. I'll simply show you five photographs...
  • On a similar note, there was once a round on tits and finches (i.e. the birds), with Richard saying that he didn't want any sniggering, they were just going to look at some lovely pictures of tits...and then, after a beat, rubbing his hands together and going "PHWOAAARRR!"
• An episode of the Australian series had an anagram question on Michael Jackson singles. One of these anagrams was "Dab", which got a score of 66, leaving Mark and Andrew baffled that 34 people couldn't figure out "Bad".
  Mark: Sorry, does this mean that thirty-four people thought that "Dab" was "Dba"?! Or "Abd"?!
• In another episode of the Australian series, the first round's category was "words with two or more syllables from Waltzing Matilda". One contestant got syllables mixed up with consonants and answered with "come." Even though the footage of the entire studio in hysterics was cut from the broadcast, Mark trying (and failing) to keep a straight face while saying "let's see if come is correct, and if so, how many people said come" made it to air.
  Mark: What's wrong with "come", Andrew?
• A January 2017 episode had the category "Artists who featured in the Top 40 Biggest Albums list of 2015". A contestant gave the answer "Alexander Armstrong", causing Alexander to laugh and thank her for the compliment—only for it to be revealed that not only was her answer correct, it was Pointless!^note Alexander is a classical performer who released his debut studio album A Year of Songs in 2015, which went on to become the 32nd biggest selling album of the year. Alexander's astonished reaction is priceless.
• One celebrity special had James Acaster ask if he could sit down. Richard replied that they weren't allowed not to sit down. Cue all eight contestants sitting down on the step separating the podiums, followed by Alexander joining them to take a selfie.
• One episode saw one of the contestants forgetting the rule that the first answer they give would have to be the one they were judged on (since they weren't yet at the end of the round). Cue him giving an answer to the most obvious clue as he was trying to "talk through the board", with both Alexander and Richard good-naturedly admonishing him for it even as the answer he gave turned out to be wrong. The next contestant, being something of a Smug Snake, mocked the previous contestant...before attempting to talk through the board himself, giving the correct answer to the most obvious clue and ultimately ending up with only a few points fewer than 100 himself. The audience, along with Richard, immediately dissolved into near-hysterical laughter while Alexander again had to point out the rules.
• On one occasion, a contestant misnamed Cressida Dick, the Commissioner of the Metropolitan Police, as "Caressa Dick". This was met by a surprising amount of silence and seriousness from the audience, contestants and hosts, making one suspect that there's a take of the entire studio dissolving into laughter and forcing a reshoot.
• The Cold Open for a 2018 Pointless Celebrities episode featuring the cast of EastEnders starts with Alexander meeting Richard at the Queen Vic, a pub frequented by the characters. As Richard provides a long, detailed rundown of the key plotlines (about 33 years' worth at the time), Alexander works his way through one pint of beer after another and begins slurring his words more and more. After three hours, we get this exchange:

  Richard: In the next, the Queen Vic caught fire.
  Alexander: What's the Queen Vic?
  Richard: What's the Queen Vic? This is the Queen Vic. It's a fake pub.
  Alexander: So this is fake beer.
  Richard: Yes.
  Alexander: Then why am I drunk?

• One episode had a round about Sebastian Faulks novels. Neither pair could name one and came up with answers (unsurprisingly, neither were correct). Richard then went on a monologue set in the Faulks household.

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