Like a Broken Record

Let's face it, its funny when audio technology goofs up, especially when it's not supposed to; it's always good to make sure that that that that that that that that that that that that that that that that that that that that that that that that that that that that.

Well, you get the picture.

For overly-long repetition not caused by a malfunctioning machine, see Broken Record.

Film

 * The Marx Brothers film Monkey Business: the boys all try to get in the country claiming to be Maurice Chevalier (he was on the ship and they stole his passport). To prove they're Chevalier they sing; Harpo's got a Maurice Chevalier record on a wind-up player strapped to his back, which eventually begins to wind down.
 * Who Framed Roger Rabbit: Roger is entertaining the bar patrons by performing to a record of "The Merry-Go-Round Broke Down" (the Looney Tunes theme). The record sticks just as Roger gets to the part where he smashes a plate over his head, so he smashes several until Eddie stops the record.
 * Played for laughs with the opening song in Hannah Montana The Movie where Hannah is shooting a music video and the song becomes stuck on 'Best of both...best of both....' until the sound engineer does Percussive Maintenance to get it going again (while the dancers also loop their moves). They finish the song, the director calls cut and says he'll Fix It in Post.
 * Singin in The Rain: At the preview showing of The Dueling Cavalier, a mishap causes the film to lose sync with the soundtrack (early sound films had the soundtrack on a phonograph record; they switched to printing the track directly on the film to avoid this very thing), leading to a scene where the villain and the Distressed Damsel speak each other's lines. This becomes a plot point, as it leads to the idea of having Kathy dub over Lena's nails-on-a-chalkboard voice.

Literature

 * Don't pick it up, pick it up, pick it— Don't pick it up, pick it up, pick it— Don't pick it up, pick it up, pick it—

Live Action TV

 * In the final episode of Are You Being Served Mr. Spooner goes on TV to become a pop idol, but he loses his voice mid-song so they play a reel-to-reel tape they recorded earlier. Problem is, the tape was recorded at half the speed it was played back at.
 * Episode 24 of Monty Python's Flying Circus, just before and during the opening titles.

Music

 * GIRL YOU KNOW ITS GIRL YOU KNOW ITS GIRL YOU KNOW ITS GIRL YOU KNOW ITS (and this one happened live!)
 * Not quite the same as this, but Ashlee Simpson's singing career went down in flames after she went on Saturday Night Live to promote her new song and started lipsyncing to the wrong song...
 * Blur's song Peach ends in a manner which is reminiscent of a skipping record.
 * Played for laughs in Type O Negative's Skip It, designed to sound like the CD is jumping.

Theater

 * Not quite the same thing, but in The Musical The Drowsy Chaperone, the Man in Chair is listening to an actual record of a 1920's show, which occasionally skips. Since the show is "appearing" in his living room, the characters have to keep repeating their actions until the record moves on.

Western Animation
"The malevolent part is one charm, without the cumbersome shackles of sentimental introspec-spec-spec-spec-spec-spec-spec-spec-spec-spec-spec-spec-spec-(slam)
 * In The Great Mouse Detective, the heroes are strapped into a Death Trap driven by a record player. Fortunately, the record starts skipping, pausing the countdown for a few precious seconds. Unfortunately, Basil is too busy having a Heroic BSOD to take advantage of it.
 * Arthur used this as an exposé for their literal Fake Band Binky, where the title character accidentally thinks a key component of the band's hologram generator is a trash can and throws a banana peel in it. You can guess what happened next.
 * One later Looney Tunes short called "Daffy's Inn Trouble" features the trope. In one scene, Daffy (in drag) decides to mime to a song on a record to lure patrons into his new inn, only for the record to start skipping. Once he's caught, Daffy attempts to do a quick dance before the would-be customers began throwing produce at him.
 * Phineas and Ferb: Perry is undercover masquerading as scientist Dr. Lloyd Wexler at an evil science convention in Britain, but when Doofenshmirtz makes Perry read from his autobiography, he almost gets caught since platypi can't speak (well in anything but that growling noise Perry usually makes). Thankfully he just happened to have a CD player and a audiobook version of said autobiography to lip sync to, until it randomly started skipping.

Doofenshmirtz: Hmm, that's funny. I don't remember you saying "spec" so many times."

"WL: GO AWAY! I'm missing Baywatch.
 * Spongebob SquarePants: In "Gary Takes a Bath", Gary plants a record player with a shadow similar to himself on a tree with his meowing playing on it. When Spongebob pours water on it, it breaks and starts skipping.
 * In another Looney Tunes short, "Pigs in a Polka", the Big Bad Wolf tries to fool the Three Little Pigs by disguising himself as a Gypsy woman playing the violin. One of the pigs discovers the record player hidden behind his back and switches the record over to an upbeat polka, causing the wolf to literally dance out of his costume.
 * Part of a gag in Animaniacs where the Warners are chasing down the Wally Llama to ask him something:

Wakko: But we have a very very very very very very very (Yakko thumps him) important question to ask you."