Old Windbag

"In after-years [Piglet] liked to think that he had been in Very Great Danger during the Terrible Flood, but the only danger he had really been in was the last half-hour of his imprisonment, when Owl, who had just flown up, sat on a branch of his tree to comfort him, and told him a very long story about an aunt who had once laid a seagull's egg by mistake, and the story went on and on, rather like this sentence, until Piglet who was listening out of his window without much hope, went to sleep quietly and naturally, slipping slowly out of the window towards the water until he was only hanging on by his toes, at which moment, luckily, a sudden loud squawk from Owl, which was really part of the story, being what his aunt said, woke the Piglet up and just gave him time to jerk himself back into safety and say, "How interesting, and did she?""

- Winnie the Pooh

A character known for droning on and on about topics of interest to no one but himself. As soon as he launches into one of his anecdotes, those present start rolling their eyes, going to sleep or having surreptitious conversations of their own. To qualify for this trope, it's not enough for a character simply to be verbose; it must be a source of annoyance and/or derision for the other characters.

Compare Blah Blah Blah, Motor Mouth, and Rambling Old Man Monologue.

Anime and Manga

 * Cilan in Pokémon qualifies. When he starts on one of his Pokémon connoisseur speeches, Iris usually gets annoyed and makes comments to the "there he goes again" effect.
 * Jessie calls one of the judges in Pokémon Advanced a "windbag" when he starts making a long, boring speech.
 * Hamtaro: The "Elder Ham-Ham" has a bad case of this. He'll start talking to Hamtaro or Bijou about one of his days as a young Ham-Ham or tell an old story, and then halfway through, he will fall asleep.

Film - Animated
""Here it comes. The Victoria Cross.""
 * Col. Hathi in The Jungle Book


 * The animated Rankin/Bass Productions special Twas the Night Before Christmas had the mayor who was like this. He'd get going on and on with big, long words, and the other characters would start yawning, rolling eyes, etc. Then he'd get tired of it himself and go "oh, heck" and do a TL,DR.

Film - Live Action

 * Sethi's court announcer in The Ten Commandments. This is exactly what everyone kept calling him..."the old windbag".

Literature
""Half-an-hour," said Owl, settling himself comfortably. "That will just give me time to finish that story I was telling you about my Uncle Robert...""
 * Owl in Winnie the Pooh

"Goddam looked mournful. "I know how it is," he said. "I was in the war. Pinned down in a deadly hail of Jap fire..."
 * Bored of the Rings, a parody of Lord of the Rings. At one point Goddam (Gollum) starts to do this for no apparent reason.

Spam gagged, and his arm went limp. "Die," he suggested.

Frito took a large loaf of raisin bread and crammed it into Goddam's mouth."


 * In the real Lord of the Rings, Bilbo has become this to most of his friends and neighbours.
 * Purdy in the Warrior Cats series. When he starts to tell a story, characters often find excuses to leave. Some of them fall asleep in the middle of his stories. Once, he actually did realize that the other cat fell asleep, and when they woke up, he informed them that they missed a lot of the story and so he'd better just start over at the beginning.

Live Action TV

 * The Twilight Zone TOS episode "Hocus-Pocus and Frisby". Frisby loves to tell tall tales about his past, much to the disgust of the regulars in his store.
 * Sheldon from The Big Bang Theory.
 * Saturday Night Live: In the Digital Short "The Tangent", a man and a woman meet on the sidewalk and he goes into a long tangent after she asks him about a restaurant he went to the previoius night. During his digression she leaves, he gets discovered as a new comic hit, goes onstage, films a movie, appears on Conan and his movie bombs. All this time he never stops talking.
 * Jonathon Higgins in Magnum, P.I. could qualify. Subverted in that he's told stories those around him (and the viewer) are supposed to find poignant, and once when he starts to tell a story, his sound is turned off, and when his sound is turned back on the people realize it could have been very entertaining.
 * Monk has the minor recurring character Kevin Dorfman. Every subject he talks about has to be talked about in depth. Even if it's just egg salad. At his funeral, all of his family members are also shown to drone on and on.

Music
"He said blah blah, blah blah, blah blah blah blah, in Tijuana, blah blah blah, back in 1963..."
 * The titular character from the song "Old Blevins" by The Austin Lounge Lizards. Blevins has some deep wisdom he wishes to share:

Theatre
"Gertrude: More matter, with less art."
 * Polonius in Hamlet

Video Games

 * Wendy Oldbag from Phoenix Wright: Ace Attorney, of course.
 * The Legend of Zelda: Majora's Mask has a sweet old grandmother who loves to tell stories. You need the help of a magical mask for Link to stay awake through that.
 * Cranky Kong in the Donkey Kong Country universe.

Western Animation

 * Grandpa Simpson on The Simpsons.
 * Commander McBragg in Tennessee Tuxedo and His Tales. At first, McBragg's guest attempts to avoid another long, boring tale, but eventually gets sucked into it... and utters the inevitable Incredibly Lame Pun at the end.
 * Animaniacs: Yakko, Wakko & Dot meet Pip Pumphandle, who gives one long labourious story as he shakes Yakko's hand. They try to get away but no matter where they go, there Pip is continuing his pointless story.