A 2011 commercial for the Citi card is told from the perspective of a makeup artist working on a film. This trope seems to be in play if the lead's cell phone going off, rain delay, and demand for a bigger explosion are any indication.
I thought we'd be on location for three days. It's been three weeks.
Funnily enough, the makeup artist in the commercial is played by Patricia Ja Lee, who has actually dealt with troubled productions in the past during her tenure on Power Rangers.
An episode of Yes! Pretty Cure 5 had Urara's first show, an outdoor stage show, go completely off the rails. The actress playing the main character falls ill during rehearsals, leading Nozomi, who was kicked out of the Drama Club after just two days, to decide to take over. Then, there was trying to get Nozomi to get through the show without klutzing out. Then, during the show, Girinma shows up and summons the Monster of the Week, forcing the girls to figure out a way to transform and fight the thing. And it is a hit! However, when Urara's manager asks her if she could pull that off again, she's left speechless and the other four vocalize what she wants to say: No way!
Funnily enough, a minor example of this happened during production. During the opening scene, Ben Stiller's character is supposed to say "alright, can we cut now?" after a scene in the Film Within a Film goes wrong. Problem was, Stiller also directed the film, so when his character said "cut", the crew mistook that for their director ordering them to cut.
A fictional example can be found in Werner Herzog's Incident at Loch Ness. To give any details would be ruining it.
As the folder for real examples above shows, it is inspired by Herzog's actual career.
Living In Oblivion is a nineties independent flick in which Steve Buscemi plays the role of a director in a nineties independent flick where everything goes wrong. The movie itself is supposedly based on the director's experience while working on a Brad Pitt movie called Johnny Suede.
The film within the film for Singin' in the Rain (The Dueling Cavalier) experiences a severely troubled production due to the transition from silent to talkie pictures; the cast and crew's inexperience with sound recording (and the leading lady's paint-peeling voice) causes numerous difficulties, leading the film to be laughed off by audiences at its first screening. It's salvaged by a hasty Re Tool into a campy musical and the redubbing of all the film's dialogue via studio recording, complete with another actress dubbing the leading lady's lines.
Shadow of the Vampire fictionalizes the production of Nosferatu highlighting the disagreements between stars and producers, director and crew, and an actual vampire.
Irreconcilable Differences is mainly about young Drew Barrymore divorcing her parents, but the best parts involve Ryan O'Neal's hilariously overblown Gone with the Wind clone spinning out of control.
The film-within-a-film of Scream 3, based on the 'real-life' Woodsboro murders, is quickly shut down when Ghostface starts targetting the cast.
Who Framed Roger Rabbit starts off with a film-within-a-film that has gone over schedule and budget due to Roger not seeing stars when the fridge is dropped on his head.
In François Truffaut's 1973 film Day for Night, the film-within-a-film Meet Pamela runs into all sorts of problems. A power failure at the processing lab ruins footage of a key scene, the lead actress is emotionally fragile after a nervous breakdown (and nearly has a second one during filming), the actor playing her husband is having serious relationship issues and nearly walks off the film, the actress playing his mother is so drunk she can't remember her lines, a cat involved in a cutaway scene keeps running away from its mark, and the middle-aged lead actor is killed in a car accident and the insurance agency won't cover the cost of reshooting his scenes with another actor.
State and Main shows examples of a lot of the production troubles of location shooting, especially the interpersonal variety; in-fighting, ego-clashes, irresponsible talent and/or management, Executive Meddling, etc.
Patrick Quentin's Puzzle for players consists entirely of this. At one point, the desperate Broadway producer explicitly writes down a list of "13 reasons why Troubled Waters cannot possibly see the light of day".
Live Action TV
Slings and Arrows has one of these every year. The first two turn out well; the third one ends with the lead actor dying and everyone else involved in the production being fired.
Part one of the Young Indiana Jones movie The Hollywood Follies revolves around Indy engaging in a battle of wits with Real Life primadonna director Erich von Stroheim over Foolish Wives.
Pretty much any of Vincent Chase's movies on Entourage (Smokejumpers, Aquaman, Medellin... pretty much all except Gatsby) fall victim to this trope.
The Community episode "Documentary Filmmaking: Redux" depicts the Dean trying to film a 30-second ad for the college and slowly driving himself and all the other characters to madness. The episode is shot as Abed's documentary, which explicitly described as the Hearts of Darkness to the Dean's Apocalypse Now.
This Is Spinal Tap depicts a tour as snakebitten as the Victory Tour (see Music for details) would be that year in real life.
The Producers, when they weren't troubling their own production, were overjoyed with the 'bad luck' that struck it, until the worst disaster: audiences loved "Springtime for Hitler".
The play being performed in Curtains! is one big screwed-up mess, thanks to a lot of back-stage drama, an entire number being badly-choreographed, the lead actress giving a terrible performance, and a whole lot of murders happening. Fortunately, the detective investigating said murders is a Promoted Fanboy who puts just as much time into improving the quality of the play.
The crappy student film Marble Hornets was called off due to "unworkable conditions," with the director getting increasingly hysterical and paranoid. Later analysis would reveal that in this case, "unworkable conditions" means "driven to near-insanity by the constant presence of a creepyguywith no face."
Metalocalypse: Every single in-universe album during the show's run. The first is done underwater in an attempt to sound as "analog" as possible, deafening the producer. But the biggest example of this trope is the second album: the band procrastinated big time getting it out, causing mass panic. When they finally got to it, Nathan demanded to perform in a suit of armor that made recording difficult, Pickles was starved while everyone else ate, Toki and Murderface produced their own song which, due to how bizarre it was, failed to even make it on the album and to top it all off, Guitarist Skwisgaar Skwigelf was forced by feedback to do his guitar parts skydiving, and thanks to Toki deleting the parts, they did it twice. And then when they did release the album, an anti-Dethklok terrorist group attacked Mordhaus, leaving said Mordhaus burned to the ground and their manager believed dead.
The best part? They experimented by recording the music ON water (It Makes Sense in Context), and then they all used the water they recorded the music on for mundane purposes.
"YOU'RE MAKING RAMEN NOODLES WITH SKWISGAAR'S SOLO!"
The album after that: well, recording itself seemed to have gone fine, but Dethklok then faced accusations of racism, and their attempts to rectify that misconception just made them look worse, then when the album was shipped, a freak storm sank the ships with all the copies of the album, and Nathan destroyed the master copy after believing that the sinking was a sign the album shouldn't exist. This caused the economy to plummet. Their first attempt to rebuilt the economy, the Dethfairs, didn't go so well. Then their usual producer, Dick Knubbler, is fired and replaced with Abigail Remeltindrinc, causing tension between Nathan and Pickles, who both want in her pants. When Nathan succeeds, Pickles, furious that Nathan destroyed the album and got the girl, quits the band. At what's supposed to be their final concert, it's attacked by Mr. Selatcia, the president of their company is murdered, and Ofdensen is forced to reveal the truth about the prophecy surrounding Dethklok to them. There is a Hope Spot when Nathan apologizes for causing Dethklok's breakup, but then the Revengencers attack, and both Toki and Abigail are injured and captured. The fourth season ends with Ofdensen saying that they need to save them if they're going to finish the album that will prevent the Metalocalypse.
An episode of What's New, Scooby-Doo? revolved around director Vincent Wong's attempt to make a re-make of a cheesy spy movie Spy Me A River. Besides the lead actor quitting halfway through, no one reading the script, Mystery Inc. being used as stunt doubles, and a Classically Trained Extra with eyes on the lead role, the production was haunted by the Faceless Phantom who turned out to be the director who wanted to sabotage the film after realising how awful it was.
The Looney Tunes short "(Blooper) Bunny" showcases every last mistake and pratfall performed by Bugs, Daffy, Elmer and Yosemite Sam. For a 20-second short for Bugs' 51 1/2 Birthday.
The three-part "Starbright" storyline in Jem. Rival band The Misfits take over the studio and cause so much trouble for Jem and the Holograms that everybody involved quits. When The Misfits retool the film for themselves, they go massively overbudget and receive a dozen lawsuits from various unions. Jem and the Holograms decide to make their own movie, and the predictable result is that theirs is a massive success and The Misfits' flops hard.
Rugrats had an episode where Phil and Lil were hired as actors for a diaper commercial. The director was a massive prima donna, Phil refused to even do a simple action (possibly stage fright) and Lil ended up causing chaos chasing down a toy car. The director gets so fed up, he kicks the twins out, with Betty all too happy to take them out. However, when the commercial proves to be a hit, the director attempts to crawl back and win them back. Betty isn't having any of it and the twins, along with Tommy (who was told this story) just walk away.