Despite the title, this is, in fact, a comedy trope. Because there is something funny about watching someone attempting to be funny and failing. To be funny, that is. It's just funny. Got it?
This is essentially a character who screws up any attempt to tell a joke. Perhaps they forget the punchline, perhaps they have no sense of timing, perhaps they try to explain it until it stops being funny, or perhaps the joke never had a chance to be funny to begin with. Whatever the case, any attempt to make a joke will leave their intended audience staring at them dumbfounded. (Or possibly laughing, but not for the intended reason, if the intended audience enjoys Anti-Humor, which this often bears unintentional resemblance to.)
For bonus irony, may be followed by a Rimshot.
Compare and contrast with No Sense of Humor.
Tien in Dragon Ball Z encounters trouble with this trope when King Kai requires all potential students to tell him a joke. He did manage a joke. Once.
Madam Red in Black Butler. We never get to hear the joke but the cast's reactions range from blank stares to confusion.
It runs in the family. When her nephew (the main character, Ciel) has to make the Undertaker laugh to get information from him, we see Sebastian wait outside as day becomes night and then day again. And after all that, the best he gets is "Pfah."
Masaomi Kida from Durarara!!. Not that it stops him from trying at every chance.
In Nichijou, the principal tells old jokes that no one gets, while Yuuko's are just terrible.
Bleach: In of the many Slice of Life sketches Tite Kubo does about his characters, there's one of Byakuya doing a stand-up routine in front of a huge audience. He holds his kenseikan to his ear and pretends it's a telephone. The audience doesn't laugh. He gets an "I told you so" from Renji afterwards. On another occasion, Renji asks Byakuya which hairdresser he uses and Byakuya tells him he gets his zanpakutou to cut his hair for him. Renji is so shocked, Byakuya has to tell him he was joking. Of course, Renji's then more panicked by the idea of Byakuya telling jokes. It's a Running Gag that Byakuya's very funny when he's not trying to be but an absolute disaster when he is.
Colossus by his own admission in Astonishing X-Men #19, after being told of a prophecy that he is destined to destroy the Breakworld:
"I have been planning on destroying the Breakworld ever since I was a child." (after the X-Men look at him in shock) "This is why I don't make so many jokes. I never know when is good."
A short Richie Rich story has Cadbury in the next room telling some very old and clichéd jokes, and in his usual stuffy British style of speaking. Gloria is puzzled when she hears laughter, but then Richie takes her into the room and shows her that the laughter is emanating from a "laugh box" that he got for Cadbury so that at least someone would find his jokes funny.
In the original The Smurfs comic, the Smurfette completely botches the joke she's telling. That does not preven all the Smurfs to find it hilarious, since she's a blonde bombshell by that point.
Marlin in Finding Nemo struggles his way through a joke in the beginning when he's put on the spot by the other parents. He makes a better fist (fin?) of it at the end of the movie.
Reportedly, Albert Brooks fell in love with the Deconstructionist aspect of Marlin - a clownfish who isn't funny - and ran with it. Word of God is that "we have about an hour of audio from Albert telling this joke really, really badly."
Dug from Up. Of course, it's possible his joke is hilarious to another dog...
Hey, I know a joke! A squirrel walks up to a tree and says, "I forgot to store acorns for the winter and now I am dead." Ha! It is funny because the squirrel gets dead.
Film - Live Action
K.C. Downing from the movie My Favorite Year. She tries to tell the protagonist Benjy that she's just not funny but he refuses to believe her. He gives her a joke and gets her to tell it back to him. He is then convinced.
Charlie tells a funny, fitting joke in Mystery Team... and then proceeds to tell the EXACT SAME JOKE not one minute later, in an entirely inappropriate situation.
Karl from Sling Blade fails terribly at telling a joke about two men on a bridge:
There's these two fellas. They're standing on a bridge and going to the bathroom. One fella says that the water's cold. Other fella said the water's deep. I believe one fella come from Arkansas.
Biff Tannen in Back to the Future is constantly, err, biffing his attempts at wordplay with lines like "Why don't you make like a tree and get out of here," and "That's as funny as a screen door on a battleship." Presumably everyone is too afraid of him to correct him. He is berated for this by his older self in the second movie.
After spending the morning being processed, he is taken to the huge mess hall for lunch. He finds a seat at a table full of inmates who look like they have been behind bars for years. Suddenly, an inmate stands in the middle of the room and yells, "41!" As he sits down, the room erupts in laughter. Then another prisoner stands and yells, "123!" Again, there is laughter throughout the room. Puzzled, Fred asks the inmate sitting next to him what's going on. "Well," the older inmate says, "Most of us have been here so long that we have heard all the jokes. So we just number them and use the number." Fred says, "I love to tell jokes! Give me one." "Okay," says the older inmate. "Everybody loves old 72. It always gets a big laugh" Fred stands up, waits for the laughter to die down from the last joke, and yells, "72!" There is nothing but silence as hundreds of inmates just turn and stare at him. Fred sits down and looks at the inmate who gave him the number. "What happened?" he asks. The older man shrugs and says, "Some people just can't tell a joke."
Lieutenant Rzhevsky attends a ball. At a certain point he notices his servant and says, ‘Ah, Stefan! I am pleased to find you here. Pray tell, have you any new rhymes for me?’ ‘Ah, yes, monsieur, here’s one I heard this morning: “Adam and Eve, on the very last eve in the wonderful Garden of Eden...’ ‘Wonderful, wonderful! Ladies and gentlemen, écoutez-vous! I just heard a wonderful new rhyme from my personal waiter... It went like... Y’know, Adam and Eve, like, in the Garden of Eden, and they f... I mean, it was their last night, so they fu... Oh, but it sounded so much better in verse!’
One particular joke uses this in a very meta sense. It starts off as a classic "Three people walk into a bar" joke, then the joke teller pretends to have forgotten or misremembered some details, with the joke getting weirder and weirder as it's told. At some point - "So, it's a nun, a dragon, and twenty four penguins, half of which are dead, in a roller disco..." - the teller gives up.
Granny Weatherwax from Discworld doesn't quite 'get' humour. In Witches Abroad, Granny keeps trying to tell a joke that goes "A man walks into a sandwich shop and sees a sign that says, 'We make all kinds of sandwiches'. So he says 'I'll have an alligator sandwich — and make it snappy!'" Only she keeps giving the punchline as "and make it quick!", or "and I want it right away!", or "and don't be a long time about it!"
Pratchett said this about it: "It is (I hope) obvious that Granny Weatherwax has absolutely no sense of humour but she has, as it were, heard about it. She has no grasp of how or why jokes work — she's one of those people who say "And then what happened?" after you've told them the punchline. She can vaguely remember the one-liner "Give me an alligator sandwich — and make it snappy!" but since she's got no idea of why it's even mildly amusing she gets confused... all that she can remember is that apparently the man wants it quickly."
In a few other books, Archchancellor Mustrum Ridcully is described as not being very good at telling jokes, and not letting that stop him.
Dan Greenberg's book How to Be a Jewish Mother contains instructions about telling jokes. One of them is always start with the punchline.
Jake from Animorphs can snark with the best of them, but when it comes to telling outright jokes, he inevitably summons the crickets. Even Ax, at one point, gets a big laugh just by repeating a joke that Jake had told earlier. Nobody laughed the first time.
Mark Twain wrote an essay about humor that explained how to do this.
Talmanes from The Wheel of Time makes some spectacularly bad attempts at humor. Mostly they fail because he's so straight-faced that his attempts at deadpan snarkery fall flat. He does manage to be amusing in a meta way, though.
At some time, somebody must have told Mister Todd that a barber, in addition to tonsorial prowess, should have memorized practically a library of jokes, anecdotes and miscellaneous rib-ticklers, occasionally including - should the gentleman in the chair be of the right age or nature - ones that might include some daring remarks about young ladies. However, that had given him this advice had simply not calculated on Sweeney's terrible lack of anything that could be called bonhomie, cheerfulness, ribaldry or even a simple sense of humour.
Harriet Hayes (Studio 60 on the Sunset Strip) is depicted as incapable of either remembering the text, structure or delivery of a joke. She's a professional comedian...
Dana, the producer on Sports Night, is referred to as being bad at jokes.
Nancy Weeks, the delightfully awful "Head of Continuing Drama" in Moving Wallpaper is alleged to be thus. in S 2 E 5, the writers are discussing whether or not to put a joke in her speech. Pope, the producer, recommends against this, saying "the woman's got the comic timing of (something)".
The Office: Michael Scott epitomizes this trope. Examples:
When Michael falls for Jim's "It smells like Updog in here" joke (punchline: "What's Updog?" "I don't know, what's up with you?"), he's so enamored with the joke that he attempts to retell it to everyone, but fails repeatedly. When he finally does properly trick someone into saying "What's Updog?" he botches the follow-up. "I'm fine, how are you?"
His original counterpart in the British version, David Brent, was also like this, due to a similar over-reliance on second hand humor from old comedy shows and a general lack of wit.
Both Borat and Ali G from Da Ali G Show have this trait. On the TV show, Borat once went on some sort of dating service and when told women like a man with a sense of humor he proceeded to tell the "joke" "There is a chair... and it has shoes... and it is walking!" In another episode, Ali G told Buzz Aldrin some sort of corny moon-based joke. He told it correctly, and when Aldrin politely laughed, Ali G was like "I don't get it".
JD from Scrubs is like this. When attempting to tell a joke about why a man who thinks he's a moth went to the dentist's (the light was on) he ends up improvising a whole pointless conversation between the man and the dentist to stall for time while he tries to remember the punch line.
And later in the episode, he gives the person he was telling the joke to a written copy of it... which covers three pages on both sides.
Carla also falls into this. Dr. Cox calls her out on it, which results in one of his Crowning Moments Of Funny, when he points out why everybody else in the hospital is funny, including calling Ted the "hospital sad sack". Dr. Cox notes that she can be funny when she's being sarcastic or arrogant, but her jokes are never funny.
If she hadn't been substituted after one season, this would probably have been a bigger part of Kate in Not Going Out. She only attempted to actually tell a joke once, and it did indeed go horribly, but Lee asked her at one point if she ever gets jokes. They just seems to be something she struggles with in general.
Zag in Zig and Zag's Nothing to do With Toast Video frequently tries to tell an elephant joke, which is invariably ruined by his inability to pronounce the word elephant.
Stargate SG-1 had an episode where Teal'c attempts to tell a joke, and fails miserably.
It's a translated Jaffa joke; presumably, it's hilarious to Jaffa (maybe there's some pun in Goa'uld that makes it work). It goes: "Three Jaffa meet on a strange planet: a Horus guard [worshipper of the hawk-headed Egyptian god Horus], a Serpent guard [worshipper of Apophis] and a Setesh guard [worshipper of a doglike god, long-lost and considered sort of like mythical bumpkins by the others]. It is a tense moment. The Horus guard's beak glistens. The Serpent guard's eyes glow. The Setesh guard's... nose drips!" And Teal'c bursts out laughing.
How is that not funny? It's the absurdity of it all. It's a tense situation. The Horus guard does something impressive, the Serpent guard does something else impressive, and the Setesh guard does something...less impressive. Setup, further setup, and Subversion.
Another SG-1 example occurs in "Citizen Joe" in which Joe Spencer seems incapable of telling a simple joke.
Monk tries a few times, as a part of trying to become more social.
Gypsy from MST 3 K, to judge from the few times she was allowed to comment on a movie.
Joel and the bots do a group impression of Rip Taylor with a string of increasingly lame, desperate prop jokes. IT'S FUNNYYY!
A Running Gag in Shooting Stars, where Vic's Once an Episode attempt to tell a Dove From Above-related joke results in silence, whistling wind, and tumbleweeds. Unless another character reads the same joke for him, in which case it of course becomes enormously amusing.
Perhaps you should introduce her to her insect reflection.
It still isn't funny.
It's worth noting that this was in a dream Giles was having while the First Slayer stalked his dreamscape, based on the fact that the real Anya is funny without meaning to be, with her oddities of behavior.
Simon from Firefly is seemingly bad at telling funny stories about working at Hospitals.
Then again, when he's going up against the possibility of Inara telling some funny whoring stories the poor guy hasn't got much of a chance.
His story about making surgeon in "Objects In Space" is much better.
Dick Loudon demonstrates this on at least one Newhart episode.
Nicola Murray in The Thick of It has the unfortunate combination of a desperate urge to not seem glum or smug and the comedic timing of a deathwatch beetle. In the first series, Olly is the one who takes on this role, as he constantly attempts to prolong jokes and, as is usually the case in real life, ends up killing them stone dead. By the time the specials role around he's even lampshading it:
Throw a blanket over me, I'm on fire!
In Star Trek: The Next Generation, one of Data's many attempts to become more human involves him trying to understand the nature of humor. He enlists the help of a holodeck comedian program, and memorizes all the jokes...then proceeds to completely botch the delivery of every one. It's hilarious to watch.
In one of the last episodes ("Journey's End"), he actually pulled a joke off perfectly, then explained that it wasn't a serious statement, killing the joke.
Monty Python's Flying Circus - as the funniest joke in the world proves an effective crippling weapon for the British in WWII, the Nazis try it themselves: An English couple listening to the radio hear a thick Germanic voice saying "Dere vere zwei peanuts valking down ze strasse, und vun vas assaulted. ...peanut." 'Deutschland Uber Alles' then plays triumphantly as the couple exchange puzzled looks.
Spencer Reid of Criminal Minds tells hilarious jokes ... if you're a genius speed-reading polymath with an eidetic memory. Otherwise, not so much.
The entire premise of Luann Lockhart on Mad TV, the amateur stand-up comedian who has no idea how to tell a joke.
Cliff Clavin of Cheers attempts stand-up at one of those amateur hour comedy clubs, and his entire schtick is endless variations of "...what's up with that?" Yeah, he bombs.
Reed from Adam-12. He spends a good portion of the finale of season one trying to tell Malloy a joke about ... a dog... and paint... or something, suffering constant interruptions from calls (not his fault) and his own disjointed retelling (totally his fault), and then he's crushed when Malloy doesn't laugh.
Andy Kaufmann in his Little Foreign Man character would do a stand-up routine with deliberately incomprehensible, unfunny 'jokes'.
On at least one occasion, KITT of Knight Rider tried to entertain Michael with pre-programmed jokes. He ended up completely messing them up, which wasn't too surprising ... but as it ended up, it was his badly-told jokes that saved Michael's life.
Why's a king's wand called a scepter? 'Cuz everyone in the kingdom works and he doesn't!
In the Red Dwarf episode "Better than Life", the newly-titled "Admiral" Rimmer is attempting to tell an anecdote, but can't remember exactly what happened. It was so bad that even the fictional officers from his ideal dream went through a couple of seconds of embarrassed, uncertain silence before bursting into sycophantic laughter.
Ferguson from the Nickelodeon sitcom Clarissa Explains It All was generally a straight-laced, snobby know it all. Later in the series, he spent an entire episode practicing the delivery of a cliche joke (A homeless man walks up to me on the street and says he hasn't had a bite in...) for some event that he was participating in. The humor came not from the joke itself, but from the ludicrous attempts at telling it, which eventually started including ridiculous stresses on random words of the punchline, a la "I bit him. I bit him. I bit him."
An episode of Supernatural has an example with Cassiel referencing a text as a joke "you breed with the mouth of a goat". This spawned the in-fandom meme "It's funnier in Enochian."
Uriel is apparently the funniest angel in the garrison. Ask anyone.
Brennan from Bones as part of her general social incompetence.
Armando from The Armando Iannucci Shows is this; when he is asked to do a speech to a group of corporate executives on the grounds that, as the writer of Im Alan Partridge, he must be funny. Armando's speech consists of Power Point explanations of various jokes, including "My Dog's Got No Nose".
Joker's Wild was a panel game from ITV, in which six comedians were each given a subject by the chairman (Barry Cryer). They had to tell a joke on this subject, and a member of the opposing team could interrupt if they thought they knew it. When Eric Sykes was on one of the teams, he played this trope for all it was worth (including, at one point, having team captain Alfred Marks go over to him and talk him through a joke).
Eric: Animals. Yes. There was this fella, and he was very strong...no, his wife was dying, that was it...she was Scottish, so Scott—no, she wasn't dying, she was pretty fit, you know... but she thought one day she might die, so she said to her husband, she said, um...
Barry: Interruption by his own captain.
Alfred: Can I retire? What with him, and now Eric...
Barry: No, no, Eric's still talking. Happy retirement.
Eric: Right—so he looked up, and he said "Don't jump"! ...No, no, you've put me right off now...no, listen, seriously, this is a real joke, I've been working on this for a week, and...
(audience laughter as Ray Martino takes his belt off and pretends to hang himself)
Eric: And she...no, he...
Barry: I'll give you five points now, Eric, we can return to this in the second half.
In the first episode of Life's Too Short, Liam Neeson's attempts at improv comedy always end being about contracting AIDs from an African prostitute.
Once an Episode on The Two Ronnies, Ronnie Corbett would sit in a chair and explain that he was now going to tell a simple joke. He would often deviate from the subject this early by something like explaining that the editor wasn't happy with how it had gone last week and had... etcetera. This inability to stick to the point that tended to result in a three-line joke taking five minutes was the actual joke.
Calvin: OK, this guy goes into a bar. No wait, he doesn't do that yet. Or maybe it's a grocery store. OK, it doesn't matter. Let's say it's a bar. He's somewhere in the vicinity of a bar, right? So anyway, there's this dog, and he says something odd, I don't remember, but this other guy says, um, well, I forget, but it was funny.
Then there was the time he tried to tell Hobbes this hilarious story he heard at school. When Hobbes tried to get him to, you know, actually tell the story, Calvin concluded that the story wasn't all that funny in-and-of itself, but the kid telling it thought it was, and it was pretty hilarious when milk squirted out his nose when he laughed.
Porkypine from Pogo fundamentally doesn't get humor.
Porkypine: This is a humorous anecdote. A goat lost his nose — the first man says, "What will he smell with now?" The other replies, "As bad as ever." Haw haw haw?
And the accountant on their album The Satanic Sketches
"...the first two provided sensible answers, while the Irishman responded in a foolish manner."
Ed from Get This could tell jokes, but many of his own sketches were ruined by his own lack of organisation and planning, and turned out being funnier in 'ruined' form than if they had gone according to plan.
Denis King suffered from this on Hello Cheeky. It wasn't so much that he forgot the jokes as it was that his smarmy delivery impacted the humor, and the fact that he'd usually make some sort of happily self-satisfied comment afterwards didn't help.
In Mass Effect 2, Joker is forced to give EDI full control over the Normandy. While he is doing so, he complains about the possibility that he might be starting a trend that will lead to a Matrix-like world, with organic life existing as batteries for the AIs. EDI comments that she enjoys the sight of humans on their knees, followed by a short pause and her saying "That was a joke." Joker's expression right after, of course, is absolutely priceless. However, it's less her being unable to tell a joke and more lousy timing: to anyone not trapped on a ship with homicidal aliens and a questionably sane AI (ie the player) it's hilarious, even without the followup.
She continues to make similar jokes in the third game, until Shepard eventually asks her to stop. She muses that her timing sub-routine needs to be adjusted. Being built from Reaper technology, it makes sense that none of her construction involved any sort of understanding of humor.
In this video by YouTube user potholer54, he singles out creationists as being this when they try to make jokes about evolution:
potholer54: Okay here's the problem: You can't make something funny by just giggling as you read it because it mentions body hair, sex and armpits, unless you're in fifth grade. You actually get much more of a laugh when you are trying to be serious.
Subverted in the 2 Stupid Dogs episode "Fun!". Little Dog gets through a joke ("Why did the orange stop? Because it ran out of juice.") twice in a row. On the third time, he forgets the joke, then immediately ad-libs a new one: "What's black and white and orange all over? A skunk eating pumpkin pie!"
Seen in Beavis And Butthead sometimes, usually from Butthead bunging up a joke. There's some joke that goes "What's the definition of a perfect woman? Three feet tall, with a flat head to hold the beer". Of course when Butthead attempts to tell this, his punchline is "Uh... I dunno, but she'd be pretty hot!". Another time he did successfully tell the "Why do dogs lick their balls? Because they can!" joke, to which Beavis replies "Um... what's so special about that? Anyone can lick a dog's balls!"
Would-be comedian Iggy Catalpa in an episode of Duckman.
In Family Guy, Stewie Griffin seems to have this issue.
Stweie: Oh, I've got a good one. Two guys are at the pearly gates and... uhm, well, I don't remember how it goes, but the punchline is that they turn out to be Seigfried and Roy.
Zapp Brannigan from Futurama - He breaks out a sexist joke to Kiff when Kiff's being followed by Amy's pet buggalo.
Zapp: Kiff, who's your girlfriend?
Kiff: She won't leave me alone.
Zapp: Did I say girlfriend? I meant wife!
Tumbleweed rolls by.
Dragon from Jane and the Dragon. It may just be that he doesn't 'get' human humour but his jokes generally leave humans scratching their heads.
Jester (telling a joke Dragon has written for him): "...That isn't a cow. That's just my cave chicken."
Jane: "How is that even a joke?"
Lolly Poopdeck from The Marvelous Misadventures of Flapjack. In "Day Without Laughter", he attempts to become a comedian, but the punchlines to all his jokes consist of really strained puns based on his own name.
Private: There's two of you! That's a great trick!
Kowalski: Private, can you recall a time when I have ever played a trick or even told a joke?
A variation in The Simpsons; Homer fails at humorous limericks. He tries to disprove this by saying "There once was a man from, I think it was Nantucket. And anyway, he had this interesting characteristic..." At this point he can't remember the rest, and Lenny and Carl just snicker at him. (There is a Running Gag throughout the series of Homer never being able to finish the "man from Nantucket" limerick, which is extremely vulgar.)
Also Prinicpal Skinner. It takes him less than 30 seconds to screw up the Who's on First? routine he is doing with Superindentent Chalmers by explaining that he doesn't mean the pronoun 'who' but rather that there is a player with the unlikely surname of 'Who' playing first base.
There have been a number of examples of guests like this over the long history of Have I Got News for You, but special mention has to go to trade-unionist Derek Hatton, whose joke about a ministerial lovechild bombed, and most of all Piers Morgan, who attempts to copy a joke from a previous week, tells it badly, and then attempts to bully the audience into laughing at it. It fails miserably, and best of all, Ian Hislop manages to tell the joke later, to much laughter. (Of course, when Hislop told it the audience were laughing purely to make Morgan's failure more personal).
Hatton also told the Ikea cabinet joke ("The Cabinet is like an Ikea cabinet; a couple of loose screws and it falls to pieces") to utter disdain. When Cherie Blair told the same joke in a speech, HIGNFY replayed the clip, and to everyone's surprise, it got a rather more positive reaction. (Paul's reaction was something like "It's a matter of timing. Fifteen years later, it's funny." It's also possible they were laughing at how cheap the set looked, and Ian Hislop with hair, rather than the joke.
Often children who have just read joke books decide to make their own jokes. Results vary.
Bad Kid's Jokes collects examples submitted by kids to a joke website. Most of them are either purely nonsensical, or else the kids missed the concept of telling jokes altogether. Definitely a case of So Unfunny It's Hilarious. Typical examples include missing the punch lines of real jokes: