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Anime and Manga
- A flashback episode of Last Exile shows how the protagonists became messengers after being orphaned. Their biggest hurdle in doing the job was retrieving the messages, which were on a ring at the end of a long pole, which had to be grabbed via flyby in an aircraft, similar to a train seizing a mailbag. They miss many times and eventually have to practice on the ground, then at slow speed, before they can do it for real.
- Happens in the one-shot manga Section 459, when the boss tests Mugen to see if he is worthy to be a demon.
- When the Admiral rearranges the fleets in Kantai Collection, the newly-formed Mobile Unit Five is a Ragtag Bunch of Misfits that can't get along and can't decide on a flagship. The girls decide to take turns as flagship on training missions. Each time, an enormous explosion at sea - followed by the dejected girls recuperating in the Repair Spa - tells us all we need to know about their degree of success.
- In Plastic Memories, Isla's attempts at retrieving Nina, a Giftia, or android, nearing the end of her service life. Chizu slams the door in each of her attempts for several days.
- Urusei Yatsura. Aratu trying to win the game of tag against Lum, notably his attempt to get past her flying ability. Each attempt results in him being carried off heavily bandaged on a stretcher.
Film - Animated
- Mulan's "I'll Make a Man Out of You" opens with a montage of all the soldiers trying and failing to retrieve Shang's arrow from the top of a pole.
- In An American Tail: Fievel Goes West there is a montage of Tiger training under Wiley Burp, bumbling through each exercise until he finally gets things right.
- The Brave Little Toaster has a montage of the appliances' failed attempts at finding ways of travelling out of the cabin.
- Chicken Run starts with a montage of Ginger's plans to break out of the farm, each one ending with her being stuck in solitary confinement as punishment.
- Quest for Camelot starts with the young heroine's father telling her the story of Excalibur, with a brief montage of men trying and failing to pull it from the stone before the future King Arthur succeeds.
- Tangled has one of Rapunzel trying to shove the unconscious Flynn into her wardrobe. Even when she finally succeeds, his fingers are still sticking out.
- Zootopia: The beginning has Judy trying to make it through a series of obstacle courses based on Zootopia's regions. She is buried in sand in the desert one, slips down a wall of ice in the tundra one, falls off the monkey bars in jungle course, and falls into a (bear-sized) toilet when she tries to use the bathroom.
Film - Live Action
- Groundhog Day has several of these. There's one for Phil's failed attempts at wooing Rita (with repeated slaps in the face), another for his attempts to save the old hobo's life, and a particularly morbid one of him repeatedly committing suicide.
- WarGames. After David Lightman learns of the possibility of a back door into the system he wants to hack into, there's a long montage of him trying various means of discovering the password needed to open the back door. In a later scene, after he sees a video of Professor Falken and his deceased son, he realizes that the password is the son's name: Joshua. And it works.
- RoboCop 2 demonstrates early on why the hero is the only one of his kind: repeated attempts to make another Robo Cop result in cyborgs that immediately self-destruct with the realization of what they have become, kill the scientists that made them, or both. Eventually an executive figures out that they need someone with a very strong survival instinct who can be coerced into taking orders.
- Cool Runnings:
- The first Training Montage consists of shots of the team learning push starts. Nearly all of their attempts end in some combination of crashes, face plants, or people running after the sled.
- A variation occurs when they're trying to find someone to sponsor their team, which leads to a montage of various company representatives all laughing at them.
- In A Knight's Tale, William's attempt to become a master jouster is at first fraught with failure, as he tries repeatedly to grab a ring with his lance or hit the shield of a practice dummy, to his friends' increasing dismay and frustration. At one point they comment that he actually seems to be getting worse, and even one of his victories leads to him being put in danger of drowning. After he finally succeeds in his training the film jumps to his first tournament, where he barely scrapes by with a win.
- Iron Man series
- The first film had a montage of Tony Stark working on parts to the Iron Man suit and having spectacular failure after spectacular failure.
- At the beginning of Iron Man 2, Tony Stark has to clear a Senate hearing, the U.S. government being nervous about his singular control of the Iron Man technology and the possibility that it might get into unscrupulous hands. To refute this fear, Tony takes control of their screens and shows what his competitors' attempts to make Powered Armor have amounted to, all of which result in sheer property damage and/or severe injury to the test pilot.
- Avengers: Age of Ultron has the Avengers (except Natasha) try to lift Thor's hammer. Banner fakes Hulking Out, Rogers manages to budge it a little, and Stark... Stark tries it barehanded, with his gloves' retrorockets, and even has Rhodes join in.
- Sam Raimi's Spider-Man. Peter has a How Do I Shot Web? montage where he tries to figure out how to, well, shot web.
- The Amazing Spider-Man 2: After an encounter with Electro overloads his web shooters, Peter is shown trying to find a way to keep that from happening, resulting in him repeatedly making batteries explode and nearly starting a fire.
- Combined with Death Montage for Black Comedy in Edge of Tomorrow. Cage is a New Meat soldier stuck in a "Groundhog Day" Loop in which he's killed in battle only to wake up alive the previous day. He finds a legendary Action Girl who was once in the same situation and asks her to train him how to survive the battleground. Cue crippling injuries from the training robots, whereupon she shoots him in the head to reset everything to start. Wake up, get trained, get injured, Boom, Headshot, wake up, get trained, make it to battlefield, Yet Another Stupid Death, wake up, get trained, get injured, Boom, Headshot, wake up, Boom, Headshot, wake up...
- Seong-geun's Robinsonade in Castaway on the Moon starts off as this, as he first attempts to hunt and catch food on the island. He tries to rig up a spear to catch fish, using a stick and a fork, but spears his own foot. Later he gets much better at it.
- In October Sky there's a long sequence of experimental rockets exploding on the launchpad before the protagonists are shown figuring out what the problem is.
- Secretariat: When Penny and her crew are trying to get commitments to breeding rights for Secretariat, with phone call after phone call, sending Ron to talk to other owners, and ending with a paper with the "No" column completely filled, because no one is willing to invest $100,000 in an as-of-yet unproven horse.
- Eddie the Eagle has two:
- It starts with young Eddie trying out different sports in preparation for his Olympic career and failing miserably at each, eventually completely filling a box with pairs of glasses he's broken in the process.
- Later there's one of his attempts on the ski jump with crash after crash after crash.
Live Action TV
- One episode of The Tomorrow People (2013) has Stephen attempting to access "Limbo" by trying to learn to stop time whilst teleporting. We get a nice montage of him and John trying to work that out, before concluding that they need a new approach.
- When the MythBusters tested the claim that dental floss can cut through prison bars, Grant initially tried to build a floss-bot out of things a prisoner could plausibly get his hands on. Cue one Failure Montage, complete with bleeped-out swearing and frustrated throwing of robot parts.
- Played with in Takeshi's Castle. Common way of advancing the show past a straightforward non-group challenge is combining footage of several people failing it with one or two succeeding to pass.
- Used frequently on The Amazing Race with some of the harder tasks. After establishing the difficulty the team or teams are having with the task, they will show said teams failing the task multiple times in quick succession, with a counter on screen to show the number of attempts the teams are taking to complete said task.
- In episode 2 of The Good Place's second season, there's a lengthy montage of Michael's 803 attempts to make his "convince four humans that they're in the Good Place while subtly torturing them" plan work with him being unable to keep Eleanor from figuring out the truth every single time (except for the one time Jason figured it out) no matter what he does.
- Jay Briscoe got one before Supercard Of Honor VII in 2013 showcasing every last one of his failures to win a singles title in Ring of Honor since the promotion started.
- Super Meat Boy has this as a feature. After you complete a level it gives you a simultaneous replay of every attempt.
- In the El Goonish Shive story "Question Mark", after Sarah discovers that she has a magic mark, there is a brief montage of her trying and failing to do various things with magic.
- In Champions of Faraus, story chapter #4, Daryl's attempts to catch a troublesome kappa are shown as a montage.
- The Angry Video Game Nerd regularly does this when a game is particularly difficult, showing clips of the increasingly frustrated Nerd repeatedly failing a section.
- Red vs. Blue:
- When Wyoming, York, and Maine are squaring off against the new Freelancer, their repeated failures as presented rapid-fire, showing just how comically outmatched they are by Tex.
- In season 12, the main cast is trying to get Felix as part of a training exercise. None of the attempts even come close.
- In Season 14 "The Triplets", interspersed with the top-ranking agents of Project Freelancer training, we also have a montage of the worst agents of Freelancer failing to get anything right in their sessions as counterpoint.
- The Demented Cartoon Movie has the ten-part montage "DiScOverIng thE meAninG oF THE ZEEKY WORDS!", a mission to Mars that fails at a different stage each time.
- Dumb Ways to Die has a series of people failing to live.
- Many Lets Players playing particularly Nintendo Hard games will often have a montage of deaths as they try to get past particularly aggravating segments.
- My Little Pony Friendship Is Magic seems to like this one a lot.
- "The Show Stoppers" has a montage early on featuring the Cutie Mark Crusaders trying and failing at various tasks in attempts to get their Cutie Marks.
- The Mane Cast during the "What My Cutie Mark is Telling Me" song in "Magical Mystery Cure." All of them save Twilight Sparkle are shown trying, and failing, to do one another's jobs.
- The Cutie Mark Crusaders, yet again, in the "Hearts as Strong as Horses" song in "Flight to the Finish." In this case the Failure Montage leads up to eventual success through teamwork.
- "Pinkie Pride" has Pinkie Pie, feeling overshadowed as resident Party Planner Pony, trying out other jobs including operating room nurse, mailmare, and construction worker.
- Regular Show had several failure montages for Mordecai and Rigby in different characters, some prominent examples being:
- Their training montage with the God of Basketball, so full of failures he declares them to be the worst Basketball players in history.
- Trying to clean up the park's abandoned ballroom, while ghosts undo everything they do.
- In an episode of Phineas and Ferb where the title characters are attempting to build a rocket, we are treated to several failed attempts, involving an equation on a chalkboard, old test launch footage, and the resulting ash-covered boys going back and modifying their equations.
- SpongeBob SquarePants:
- In "Pickles", SpongeBob has trouble doing things right, and there's a montage of him trying to figure out how to get into bed.
- In "Missing Identity", SpongeBob tries to retrace his steps to find his missing name tag by repeating everything he did that morning, from tripping down the stairs to tasting Gary's food to saying hi to Patrick. Unfortunately, Patrick keeps flubbing his lines, meaning that they have to go through the whole thing over and over.
- Combined with Travel Montage in The Legend of Korra, as Team Avatar travels the Earth Kingdom trying to recruit the newly-awakened Airbenders, and showing Tenzin's utter lack of salesmanship as he unsuccessfully tries to convince each one to come learn the Air Nomads ways. True to Tenzin's usual form, each sales pitch he gives is (technically) accurate, but framed in the worst possible way for each specific candidate. He tells the overweight glutton about their vegetarian diet, the overly-fashionable one about their uniform robes, the materialistic one about their ascetic lifestyle, and the parents of a child about their tradition of tattoos.
- Action League Now had a Clip Show involving the Action League standing before council to see whether they should retain their hero status or be declared a danger to the public for their incompetence. Each of the Leaguers' flashback to their past exploits don't really help their case, but the icing on the cake is Flesh's recollections which are presented in such a montage of how his clumsiness or carelessness only did more harm than good to the people he was trying to help.
- In The Simpsons episode "Homer the Smithers", Homer is Mr Burns' assistant instead of Smithers who's on vacation, and Homer's making Burns breakfast. Every single meal he's trying to make ends up catching fire, even when he pours milk on cereals.
- There are a number of scenes in the show showing Homer industriously at work in his workshop, resulting in a sorry tangle of lumber and nails.
- The Kim Possible episode "Blush" begins with several quick scenes of Dr. Drakken gloating at Kim that she is about to witness his ultimate victory, followed by Kim derailing his plan as usual. Each defeat required less and less effort on Kim's part, elevating Drakken's humiliation alongside.
- Looney Tunes: The Roadrunner and Coyote short "To Beep or Not to Beep" ends with the Coyote getting a catapult with which he intends to flatten his nemesis... somehow, that is if he can get it to work right, since it keeps landing on him. No matter where he stands, the boulder (or another part) lands on him, until he finally hides underground, at which point the thing doesn't do anything at all.
- Kaeloo: In Episode 80, a montage is shown of Stumpy losing at beach volleyball. The final scene in the montage makes it look like he's going to finally hit the ball, but he fails that too in an Epic Fail.