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Anime and Manga
- Tomoe from Sasameki Koto had to skip a year in order to save her family's company from bankruptcy (yeah, she is a Teen Genius, alright), so she is basically one year older than the rest of the cast.
- Nagisa from CLANNAD had to repeat her senior year due to her poor health. Twice. She and Tomoya would not have even met had she not been held back the first time. Tomoya himself nearly ended up flunking out due to delinquency.
- Milly Ashford in Code Geass deliberately held herself a back a year so she could be with her friends longer. She was unwilling to leave home and join the real world.
- In Sand Chronicles after disappearing for a few months, Fuji comes back to school and has to repeat the year.
- In High School Of The Dead, it's mentioned that Rei Miyamoto was held back for a year, which is implied to be one of the reasons she and Takashi grew apart. It is later revealed that Shidou altered her grades to threaten her father, a police officer who was investigating Shidou's father for political corruption.
- In Popcorn Avatar, Kurando's sister Mafuyu is still in second year middle school due to her accident and the resulting rehab, despite being the same age as he is.
- Kaoru Orihara from Oniisama e... should be a second-year, but is in Nanako and Mariko's first year class due to having been ill last year. Said illness is cancer, and it comes back later.
- In Peach Girl Sae is held back a year and unable to graduate from high school. However despite this she pretends to be a college girl to hide it from her friends.
- Kei Yoshikawa in The Day of Revolution left school partway through his freshman year when a minor health crisis revealed he was genetically female. Six months of medical treatments later Kei returns to repeat Freshman year as a girl hoping that pronouncing her name Megumi will prevent her old crowd from noticing her resemblance to their missing friend Kei.
- Eventually happens to Shiho in Private Actress, as she has to repeat her last school year for all the inconsistencies related to her P.A work. Specifically, the Boarding School case took her several weeks to resolve, and that was the last straw for the school authorities. The last scene of the case has Shiho screeching against Kana, the Big Bad, for this reason.
- Koushaku Chouno (Papillon) of Busou Renkin had to repeat some grades because of his chronic health problems.
- Yota of Video Girl Ai is badly injured trying to save Ai from her sadistic creator shortly before end-of-year exams and is forced to repeat a year. This doesn't seem to affect his relationship with his old friends, however. Note that the OVA series, which ends at this point in the story, does not mention him getting held back.
- The Heart of Thomas: Oskar Reiser traveled with his father for a year and a half after his mother's death; by the time his father drops him off at a boarding school whose headmaster is Oskar's biological father, he's one grade behind.
- One Archie Comics story had Jughead discovering he had never graduated grade school, having been out sick the entire last week. He took a make-up test to prove he deserved to be in high school, and the last panel showed him back in grade school, having to repeat the sixth grade.
- Another story has him overhearing Miss Grundy talking about his test scores and suggesting he didn't belong in his grade. He's utterly depressed at the thought of getting sent back a grade, until she tells him he's been testing super smart and should be moved up a grade. (He opts to stay where he is, with his pals.)
- The Bells of St. Mary's: A point of argument between Sister Benedict and Father O'Malley. Patsy has failed her exams, and on that basis, Sister Benedict wants to hold her back. Father O'Malley wants to pass her, on the grounds that St. Mary's should be in the business of helping its students. Subverted when Patsy eventually reveals that she failed her exams on purpose in order to stay longer at St. Mary's.
- Ben Affleck's Fred O'Bannion, from Dazed and Confused.
- Josh Hartnett's Zeke Tyler, from The Faculty.
- In Scooby-Doo! The Mystery Begins Shaggy reluctantly admits that he was held back twice when the others in the teenage Mystery Gang ask how he has a driver's license already.
- Marcus Flint from the Harry Potter series had to repeat his seventh year per Word of God.
- This happening to Shogo Kawada is the reason he had to participate in Battle Royale's Program not once, but twice.
- During the Baby Sitters Club series, Claudia ends up getting demoted from eighth to seventh grade.
- In Edmondo D'Amici's Heart, Gentle Giant Garrone was held back two years after being seriously ill.
- A children's book named "The Flunking of Joshua T Bates" has the main character repeat the third grade because he can't catch up with his reading. It shows that he gets relentlessly taunted by his peers, but he manages to get through the year thanks to a sympathetic teacher. Both aspects are startlingly (and heartwarmingly) realistic.
- Eff in Thirteenth Child missed most of a school year due to a serious illness, which is why her twin brother is one year ahead of her.
- Patricia Reilly Giff's Polk Street School series starts with Richard "Beast" Best being forced to repeat second grade.
Live Action TV
- Oz from Buffy the Vampire Slayer is the "highest scoring person ever to fail to graduate". He got held back because he had several incompletes and didn't go to summer school for to make up for them.
- James Franco's Daniel Desario, from Freaks and Geeks.
- In the Red Dwarf episode "Dimension Jump", we are led to believe that Ace Rimmer progressed normally at school while Rimmer-prime was held back. However, it's revealed at the end that the opposite is true: Ace was held back, which made him work harder at life.
- In order to keep the some of the cast still in high school past graduation, Degrassi: The Next Generation will occasionally hold a few students back.
- In season 5, Spinner ended up repeating his junior year due to his expulsion regarding the school shooting and zero tolerance for bullying. Jimmy missed too many days due to his rehabilitation after being paralyzed in said shooting and had to repeat his senior year. Ashley actually skipped her senior year in order to study music in London, and returned at the end of the season. Alex subverted it: she graduated that season, but then came back for a "Victory Lap" in season 6 in order to boost her grades for university.
- In season 11, Fiona missed most of her classes due to a combination of her alcoholism and her going to rehab to treat it, causing her to repeat her senior year.
- In season 12, Imogen failed to hand in most of her assignments and had to repeat her senior year. Drew dropped out early in the season, and thus had to do the same. Subverted with Mike; like Alex he was doing a victory lap, the only difference being he didn't actually walk the stage and officially graduate.
- In addition, several characters were mentioned to have been held back in their backstories - Sean starts the show repeating grade 7, Mia had to repeat grade 8, Tori had to repeat grade 4, and Jonah had to repeat grade 11.
- In the original series, Rick was repeating seventh grade in the first season, and Joey Jeremiah was held back in eighth because he barely passed, and his parents and Mr. Raditch thought he should retake the year so he could start high school on the academic rather than the vocational track.
- Kelso on That '70s Show was held back as a kid and kept it secret out of shame. It fits the role of Kelso as the group's resident idiot, and he takes some shots at him when they hear it. The main joke however is that he was old enough to legally buy beer for them and told nobody.
- On Arrested Development this has happened to Steve Holt three times. There's a Freeze-Frame Bonus when his various yearbooks are shown and his most recent quote is "study hard guys - trust me"
- In an episode of Everybody Loves Raymond, Ray and Debra are debating whether or not to hold the twins back a year in school. This leads to a shocking revelation for Raymond: his mother made him repeat a grade in preschool, not for academic reasons, but because she enjoyed walking him to school.
- In The King of Queens, Doug's parents admit to him that he had to repeat kindergarten. At the time they had told him it was "Super Kindergarten".
- In Lizzie McGuire, Kate confides to her best friend, Claire Miller, that she got held back when she was in Kindergarten. When Lizzie and her friends find out, Lizzie's animated alter ego incredulously wonders how that's even possible ("What'd she do? Fail naptime?"). This gets a Continuity Nod later on, when Kate sheepishly admits to being a year older than the other kids in her grade.
- In the Community episode 'Mixology Certification', Troy was revealed to have repeated fifth grade:
Troy: Everyone is ten for two years, because fifth grade is hard for every... one... Mom! How many lies have I been living!
- Rerun on What's Happening!! has been held back a couple of times. In fact he got the nickname Rerun because he has to repeat in the summer what he didn't learn in the winter. At one point in the series he has the chance to pass and finally graduate but he's afraid to even take the test despite studying hard for it because he's not sure what he can do beyond high school.
- In Unhappily Ever After older son Ryan has to repeat his senior year of high school. Done in part so they didn't have to write the character out; then the next year he and his sister Tiffany go to the local community college.
- The Suite Life on Deck: In On Deck, Miss Tutweiller stated that London won Senior Prom Queen three times. Also, in Life of Zack and Cody, London was in the same class as Maddie at Our Lady of Perpetual Sorrow, though is in Zack and Cody's class at Seven Seas High School, despite being years older than them (she was stated to be 15 in the first season of Zack and Cody while the twins were around 12).
- In one of the final episodes, Miss Tutweiler struggles to help London pass Spanish class in order to finally meet the minimum standards for graduation, and confirms that she has been held back at least twice, explaining why she is in the same class as Zack and Cody.
- Flay has to repeat his senior year in Mana Khemia: Alchemists of Al-Revis. This enables him to remain in the party despite his being a year older than the protagonist in a game that follows the protagonist's time at the titular school.
- Senran Kagura Shinovi Versus has Miyabi and Imu, but 21 and having to repeat their senior year. An odd example, because they had already graduated from a Shinobi school, but after an incident left Miyabi catatonic for years and Imu taking leave of her duties to care for her, the two are so rusty they need to retrain to re-earn their rank.
- Yasuhiro Hagakure from Dangan Ronpa, who was held back at least two years. He's a bit... off.
- Emi Ibarazaki from Katawa Shoujo. She's one year older than Hisao and the other girls; considering that she lost her legs and her father in an accident and spent at least a year in full rehabilitation, it's fully understandable.
- In The Order Of The Black Dog Julia King had to repeat a year, which causes her classmate Melissa some confusion. Though her cast profile indicates it was due to her problems with authority, she's an Astrophysics major and gets an internship at the space center.
- Gunnerkrigg Court: Antimony is forced to repeat a grade when her long-absent father reappears and learns that she's been systematically copying Kat's work.
- The Simpsons:
- The episode "Bart Gets An F" revolves around Bart attempting to pass a history test to avoid being held back a year. He fails, but Mrs Krabapple takes pity on him when he proves to her that he had indeed studied by rattling off an obscure fact that hadn't been on the test.
- Another episode had Lisa promoted from 2nd grade to the 3rd, and Bart demoted from the 4th to the 3rd.
- In the episode where Homer gets a job in Cypress Creek, Bart is busted down to the remedial class because he never learned cursive. note
- Binky on Arthur is in his 2nd year of 3rd grade.
- Buster is (sometimes) scared that he'll be held back.
- Also on Arthur: Brain's deep dark secret is that he was held back in kindergarten.
- Francis, the menacing grey kid who bullies Timmy Turner, is mentioned to be twelve-years-old, but he's still in 5th-grade—depending on when his birthday is, he probably got held back at least once.
- Sheen, the sidekick in Jimmy Neutron, may also have been held back (or in danger of same).
- It was stated in the episode "Jet Fusion" that he had already been held back twice.
- According to his Nick.com character bio, Nick was held back at least once due to his constant tardiness.
- In the Grand Finale of the Nickelodeon version of Doug, Roger tells Doug that he's been in sixth grade for three years due to being scared of the big change it would entail.
- Daria averts Graduation for Everyone by having Kevin fail his senior year of high school while everyone else in Daria's year gets to Graduate from the Story.
- Bonnie from Kim Possible had to take summer school to graduate as she skipped the last week of school which consisted of several pop quizzes.
- Trina Riffin from Grojband has been held back for three years, despite her intelligence.
- Harold in Hey Arnold! has a bar mitzvah (the ceremony happens at 13) despite being in fourth grade. It's never stated outright how many years he's been held back, but it's either three or four.
- The website for The Amazing World of Gumball describes Jamie as being held back a year and very resentful about it.
Anime and Manga
- Raimu-sempai in Bakuon!! was at least twenty when the current principal was a student herself. She's still at school and since she never takes off her helmet, her true age remains a mystery.
- Evangeline and Sayo in Mahou Sensei Negima! have both attended school much longer than they should have. The immortal vampire Evangeline was cursed by Negi's father to attend school. Said curse was only supposed to last until graduation, but since Nagi's gone missing no one could undo the curse. Sayo on the other hand is just haunting the school where she died so many years ago.
- Karen in My Monster Secret has been the student council president for twenty years.
- Exaggerated in the The Baby-Sitters Club fanfic Caludia Keeshi Middel Skol Mamma, where, ten years after the series ended, Claudia is still in the eighth grade, because she can't be arsed to apply herself and pass the exit exam. Her former charges are now her peers (and some are her fellow BSC members) and her former classmate Cokie is now her gym teacher. It's pretty clear too that, aside from having a car and breast implants, she still has the mentality of a thirteen year old (and even hit on a kid with the justification that 'we're in the same grade'). She finally passes the exit exam at the end and declares how much she'll enjoy starting high school (at age 23-24) with the rest of the club.
- The funny thing is she thinks Claire Pike had it worse: Claire had to repeat fourth, fifth, and sixth grade.
- From Better Off Dead:
Charles De Mar: Lane, I've been going to this high school for seven and a half years. I'm no dummy.
- Micah in Easy A is repeating his senior year of high school for the fourth time. This becomes a plot point of some note later in the film.
- Timmy does this deliberately in A Fairly Odd Movie: Grow Up, Timmy Turner! as a way so he can keep his fairies since if he still acts childish, then he won't have to lose them (That is until the Power of Love begged to differ). He still in his current grade but is 23 years old. Though behind the scenes, it was a way to get an actor to play the role without worrying about him growing if they decide to do a sequel (which they did).
Live Action TV
- In Phil of the Future Phil is sent back to second grade to gain legible handwriting, because by the time the Diffy family came from, handwriting is essentially obsolete.
- A non-literal example with Johnny in Twin Peaks who is described as being a 27 year-old who's still in third-grade. It's clear however that Johnny has mental issues and he was being privately tutored by Laura Palmer.
- One Mr. Young episode had a scene which shows Slab graduating high school while in his 70s at least.
- SCTV - on "Half Wits", a 'Jeopardy'-style quiz show, Martin Short is contestant Lawrence Orbach, about 30 years old, going bald, and still in school. The host asks 'Postgraduate work?' and he replies 'High school.'
- Thanks to a ridiculously light course load that was scattered all over the place, it takes eight and a half years for Dauber of Coach to get his college diploma... in Physical Education, English, and Forestry. The reason Hayden made him an assistant coach in the first place was so that his protege could stay in college after his football scholarship ran out at the end of year four.
- In the Series Finale of Due South, Fraser and the second Ray meet a schoolmate of Fraser's... from fourth grade. Said friend looks to be about twenty years older than Fraser. He was held back a bit.
- It's implied in the vid comics for Ratchet & Clank: Up Your Arsenal that Captain Qwark had been held back in 9th grade. And he was still there at age 26, when he served as The Bully to a 15-year-old Dr. Nefarious, apparently causing the latter's Start of Darkness.
- Daidouji from Senran Kagura has been deliberately refusing to take her graduation exam, causing her to repeat third year in Hanzou Academy for ten years. It is because she wants to defeat her friend Rin before she thinks she is worthy to graduate.
- This trope is the main plot of a category of Go Animate "Grounded" videos, wherein usually two students start out in the 12th grade and keep knocking themselves all the way back to preschool before being expelled and sent home (with predictable results) by getting themselves in trouble by injuring a classmate or teacher, being disruptive, and/or merely making someone mad.
- In The Emperor's New School It was discovered that Kuzco did not complete his requirements for Kuzcogarten, and he was sent back there to complete them.
- The Simpsons:
Nelson: Yup, I've been held back more times than I can count. Which is probably why I've been held back so much.
- When Sideshow Bob was elected mayor, Bart was demoted to Kindergarten as revenge for getting him sent to prison in the first place.
- Kearny is actually an adult in elementary school. In real life he would have gotten a social promotion, but Rule of Funny.
- Similarly, Nelson appears to be a case of this, being in fourth grade with Bart:
- In the episode "Bart Gets an F", Bart has an Imagine Spot of him in his 30's or 40's, still in 4th grade alongside Bart Jr.
- In the episode "You Only Move Twice", Bart attends the school in the planned community the family has moved to. Since he comes from a decidedly Sucky School, he is placed in the "Leg Up" program, which is supposed to be a remedial class, but comes across more as either a special ed class or a kindergarten class… or a special ed kindergarten class.
- In My Life as a Teenage Robot, Jenny is sent to kindergarten because despite being, well, a teenage robot, she has only been built for five years.
- In a TV-era Popeye Cartoon, Olive Oyl refuses to date Popeye unless he can get an "edumacation". He first starts out in the eighth grade but bungles so many times that he eventually gets demoted all the way to Kindergarten. He needed to eat spinach to have the courage to spell "cat". In the end, he impressed Olive by telling her he went through all grades in one day.
- Family Guy: In one episode, Peter Griffin encounters an angry bear while on a hunting trip with his son, and his life flashes before his eyes. Twice, Peter sees himself being told by the principal that he'll have to repeat 4th grade, then his final memory before catching up with the present:
Principal: Congratulation Peter, you finally passed the fourth grade!
Peter: That's great, but I gotta leave for a hunting trip with my son.
- In another episode, Peter Griffin has to repeat the 3rd grade in order to receive a promotion.
- My Little Pony: Friendship Is Magic: In "Lesson Zero", Twilight Sparkle (who panics and assumes the worst consequences any time the possibility of failing Princess Celestia comes up) becomes convinced that, if she's tardy in sending her weekly letter to Celestia, she'll be sent all the way back to Magic Kindergarten.
- Hey Arnold! had Torvald, a boy who had been held back in fourth grade for several years.
- Also Harold being held back in fourth grade for several years.
- An episode of Beavis And Butthead called "Held Back" had the boys be continuously demoted due both to stupidity and poor social skills. They end up back in high school because the Kindergarten teacher refuses to put up with them any longer.
- More Arthur: Buster was once so afraid of being held back, he had a dream that he'd been held back for so long, Arthur had become the principal while Buster was still a student, and was offering to send him back to preschool. (In a school where, in reality, the other 3rd grade classes are practically at that level, anyway.)
- Parodied in the What A Cartoon! Show short "Larry and Steve". At one point, Larry mentions that he spent six years in kindergarten, but he insists it wasn't because he was stupid. He simply got his foot stuck in a radiator.
- Implied in the case of Brick Flagg from Kim Possible, because when Ron's trying out for the Middleton High football team to fill the spot Brick left, Mr. Barkin (the coach for the team) explains to the people trying out for the team that Brick had finally graduated after seven years — meaning that Brick was either held back three times or it took him seven times to graduate.