History Funny / Pointless

--> '''Richard''': I don't know what you're all laughing at. Ill simply [[DiggingYourselfDeeper show you five photographs...]]

** Series 5, Episode 45: Matt's reaction to himself and his Dad winning the jackpot is a laugh riot. He starts celebrating... all around the show's set while screaming.

* January 5, 2012 - The Head-to-Head round is "Capital Cities of South America". It's either Nick and Charlie or Patrick and Chris who will be making it to the final. Chris comes up with "Paranibo", a complete botch-job of "Paramaribo", the capital city of Suriname. Needless to say, the misspoken variant was incorrect, and this cost him and Patrick out of the game.

* One celebrity special had Creator/JamesAcaster ask if he could sit down. Richard replied that they weren't allowed to sit down. Cue all eight contestants sitting down on the step separating the podiums, followed by Alexander joining them to take a selfie.

* In an episode with the question being about British [=MP=]s named David, Nick or Ed (the names of the leaders of the three political parties), one contestant admitted she had no idea and picked an answer by taking one of the names and a colour. Her answer - Nick Brown - [[https://youtu.be/5WcN6m-yHTQ?t=1479 was Pointless.]]

* The intro for a 2018 ''Pointless Celebrities'' episode featuring the cast of ''Series/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:

* In one of the celebrity specials Ravi Bopara is trying to think of a Creator/BradPitt film, 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.

* 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.

* One Head to Head Question was [[https://www.youtube.com/watch?v=9SzsM7BCbkQ "Things That Rick Astley Is 'Never Gonna' Do..."]]

* The 300th episode began with Richard and Alexander exchanging gifts. Richard got Alexander a [[RunningGag 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[[/note]]

* 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.

** 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

* 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 Music/JamesBrown. 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 [[https://en.wikipedia.org/wiki/Jim_Brown 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 [[NeverLiveItDown 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.

* June 21, 2013; the category is "assassinated people". When prompted a clue "[[UsefulNotes/JohnFKennedy Assassinated by Lee Harvey Oswald in Dallas]]", one contestant replied "[[{{Series/Dallas}} 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 UsefulNotes/JoanOfArc for "French Revolutionary Stabbed in the Bath by Charlotte Corday".
* In one of the celebrity specials Ravi Bopara is trying to think of a Brad Pitt film, 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 pair of personable young female contestants reached the jackpot round and were given the categories "Solo [[Music/SpiceGirls Spice Girl]] Albums", "Children of Spice Girls" and "Actors in Film/{{Spiceworld}}". 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...

* The contestant who, faced with the category of "famous guitarists", suggested "Lenny Hendrix".

* 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.

* The 300th episode began with Richard and Alexander exchanging gifts. Richard got Alexander a [[RunningGag 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]]It's actually purely for show and not switched on[[/note]]

* In an episode with the question being about British [=MP=]s named David, Nick or Ed (the names of the leaders of the three political parties), 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.

* The intro for a 2018 ''Pointless Celebrities'' episode featuring the cast of ''Series/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, 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: