History Main / HeldBackInSchool

* ''VideoGame/SenranKagura 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.

* In the ''WesternAnimation/MyLifeAsATeenageRobot'' episode "I Was a Preschool Dropout", Jenny's sent to kindergarten because despite being, well, [[ExactlyWhatItSaysOnTheTin a teenage robot]], she was built only five years previously. She eventually gets out of it on a technicality when her [[MotherlyScientist mom,]], Dr. Nora Wakeman, explains that while Jenny may (chronologically speaking) be only five years old, the robot had been designed as a teenager.

'''Peter''': Awm great! Listen, I gotta leave though, I'm going hunting with my son.

--->'''Principal''': Congratulation Peter, you finally passed the fourth grade!\\
'''Peter''': That's great, but I gotta leave for a hunting trip with my son.

Due to there being a stigma surrounding it, characters who are held back are AcceptableTargets - expect this to be used as proof that the character is an idiot, and not just BookDumb either. Characters who are held back are rarely portrayed sympathetically - and when they are, they often keep this as a hidden shame. This is especially the case in the United States where "No Child Left Behind" laws make it much harder to fail.

[[folder:Films]]

* ''WesternAnimation/HeyArnold'' ** Harold 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.

** A variant comes up in another strip. Calvin says that he doesn't feel like going to school for most of the year for various reasons and concludes that there would be only two days per year he'd feel like attending. They discuss what it would be like if Calvin got his way and only had to attend for those two days, and Hobbes concludes that Calvin would be a very old man by the time he got to second grade.

* In ''Film/ScoobyDooTheMysteryBegins,'' 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.

** Implied in the case of Brick Flagg, 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 [[ExaggeratedTrope seven times to graduate]].
** [[AlphaBitch Bonnie]] had to take summer school to graduate as she skipped the last week of school which consisted of several pop quizzes.
* In the ''WesternAnimation/MyLifeAsATeenageRobot'' episode "I Was a Preschool Dropout", Jenny's sent to kindergarten because despite being, well, [[ExactlyWhatItSaysOnTheTin a teenage robot]], she was built only five years previously. She eventually gets out of it on a technicality when her creator/mother, Dr. Nora Wakeman, explains that while Jenny may, chronologically-speaking, be only five years old, [Dr. Wakeman] had ''designed'' [her daughter/creation] to be a teenager.

** In "[[Recap/TheSimpsonsS8E2YouOnlyMoveTwice You Only Move Twice]]", Bart is busted down to the remedial class because he never learned cursive. [[note]]Rather ironic these days, as schools across the United States (even the good ones) have been dropping cursive as a dedicated subject, preferring to spend time on core subjects that will be covered on the standardized tests.[[/note]]

** Kearny is actually an adult in elementary school. In real life, he would have gotten a social promotion, but RuleOfFunny.

* It's implied in the vid comics for ''VideoGame/RatchetAndClankUpYourArsenal'' that [[TheDitz Captain Qwark]] had been held back in 9th grade. And he was still there at age '''26''', when he served as TheBully to a 15-year-old [[BigBad Dr. Nefarious]], apparently causing the latter's StartOfDarkness..

** Implied in the case of Brick Flagg, 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 [[UpToEleven seven times to graduate]].

* Nagisa from ''VisualNovel/{{Clannad}}'' is repeating her senior year due to her [[IllGirl poor health]], and ends up having to repeat it ''again'' after most of the other characters graduate. 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, though he does graduate with everyone else in his year.

* In ''Film/ScoobyDooTheMysteryBegins,'' 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.

* Harold in ''WesternAnimation/HeyArnold'' 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. Torvald is also 13 and in the same 4th grade class as the other main kids. He starts off as a bully but after Arnold helps tutor him at math with positive results, he becomes a lot nicer. In a later episode, he joins the kids' football team against the 5th graders because he's technically a 4th grader despite Wolfgang's protests.

* Creator/JeffFoxworthy includes in his routines,

* Exaggerated in the ''Literature/TheBabySittersClub'' fanfic [[https://www.fanfiction.net/s/2177005/1/Caludia-Keeshi-Middel-Skol-Mamma 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'). [[spoiler: 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.

* Timmy does this deliberately in ''Film/AFairlyOddMovieGrowUpTimmyTurner'' as a way so he can keep his fairies since if he still acts childish, then he won't have to lose them [[spoiler:(That is until the PowerOfLove 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).

* In ''Film/ScoobyDooTheMysteryBegins'' 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.

** Catherine, Moira and Jane from the fifth form where left behind from the previous year.

* ''Literature/WarriorCats'': Swiftpaw and Brightpaw were repeatedly left back from becoming warriors and kept as apprentices. They try to chase off a group of dogs in hope that saving the clan will help show that they're worthy warriors, [[spoiler:but it ends in Swiftpaw dead and Brightpaw seriously injured and blinded in one eye]].

* Thanks to a ridiculously light course load that was scattered all over the place, it takes eight and a half years for Dauber of ''Series/{{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.

* ''Series/{{Riverdale}}'': Archie himself is held back in school in season 5, missing out graduation, because [[VigilanteMan the various shenanigans]] he did the previous year meant [[SurprisinglyRealisticOutcome his grades weren't sufficient for him to graduate]]. Instead of repeating senior year, he chooses to leave Riverdale and join the army.

* A non-literal example with Johnny in ''Series/TwinPeaks'' 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.
* In ''Series/UnhappilyEverAfter'' 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.

** In "He Eats Asparagus", it is revealed that "the boy next door" whom the protagonist is often unfavorably compared to is 34-years-old, despite (apparently) attending the same school as the narrator. However, it's never mentioned what level of eductation their school is (it might be a graduate school, for all we know), and it's not too clear whether the guy is actually there as a fellow student or a teacher.

* WebAnimation/StrongBadEmail #110, "For Kids", has Strong Bad cite this (along with "low standardized test scores") as the eventual fate for any childen raised on an "educational" show hosted by resident {{Cloudcuckoolander}} Homsar. To his credit, he admits beforehand that his ''own'' TV series would have resulted in public riots for his likely antagonism to the audience (as an InteractiveNarrator, he'd have no patience for his wards not immediately answering correctly).

* ''WesternAnimation/TheFairlyOddparents'': 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.

* In the ''WesternAnimation/MyLifeAsATeenageRobot'' episode "I Was a Preschool Dropout", Jenny's sent to kindergarten because despite being, well, [[ExactlyWhatItSaysOnTheTin a teenage robot]], she was built only five years previously. She eventually gets out of it on a technicality when her creator/mother, Dr. Nora Wakeman, explains that while Jenny may, chronologically-speaking, be only five-years-old, [Dr. Wakeman] had ''designed'' [her daughter/creation] to be a teenager.

** A variant comes up in another strip. Calvin says that he doesn't feel like going to school for most of the year for various reasons, and concludes that there would be only two days per year he'd feel like attending. They discuss what it would be like if Calvin got his way and only had to attend for those two days, and Hobbes concludes that Calvin would be a very old man by the time he got to second grade.

* In ''Series/LizzieMcGuire'', [[AlphaBitch Kate]] confides to her [[GirlPosse best friend]] [[BetaBitch Claire Miller]] that she got held back when she was in Kindergarten. When Lizzie and her friends find out, Lizzie's [[GreekChorus animated alter ego]] incredulously wonders how that's even possible ("What'd she do? Fail naptime?"). This gets a ContinuityNod later on when Kate sheepishly admits to being a year older than the other kids in her grade.

* In Edmondo D'Amici's ''Heart'', GentleGiant 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 [[KidsAreCruel 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.

* By the end of ''Manga/{{Parasyte}}'', Shinichi loses a school year due to [[spoiler:having spent most of it hunting * Evangeline and Sayo in ''Manga/NegimaMagisterNegiMagi'' 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.
down the malevolent Parasytes with Migi's help]].

* ''Literature/RainReign'': Rose Howard, who has Asperger's, is in fifth grade despite being almost twelve because the school doesn't know what to do with her.

* Amane in ''VisualNovel/IfMyHeartHadWings'' deliberately refused to graduate for almost ''ten years'' because her high school was a special engineering school that boasted great facilities, which she needed to produce the glider she had been working on ever since making a close friend as a teenager there.

* ''Webcomic/GunnerkriggCourt'': Antimony is forced to repeat a grade when her long-absent father reappears and learns that she's been systematically copying Kat's work.

* In [[https://youtu.be/pXAC4DYzuo4 Mr. Toucan Gets Held Back]], Mr. Toucan is in eighth grade at first and gets held back all the way to preschool for disruptive behavior. And then he gets expelled from preschool.

* In ''WesternAnimation/TheEmperorsNewSchool'' It was discovered that Kuzco did not complete his requirements for Kuzcogarten, and he was sent back there to complete them.

* [[AlphaBitch Bonnie]] from ''WesternAnimation/KimPossible'' had to take summer school to graduate as she skipped the last week of school which consisted of several pop quizzes.

* Implied in the case of Brick Flagg from ''WesternAnimation/KimPossible'', 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 [[UpToEleven seven times to graduate]].

** In one episode, Don Ramón is assisting Profesor Jirafales' class, at first as an excuse to escape from Doña Florinda, later, she and Profesor Jirafales agree to allow him in class, as he could use some good education.* In the ''Series/{{Community}}'' episode 'Mixology Certification', Troy was revealed to have repeated fifth grade.

** In "He Eats Asparagus", it is revealed that "the boy next door" whom the protagonist is often unfavorably compared to is 34-years-old. The lyric is not too clear whether his presence in class is as a student or a teacher, although the narrator says that he loves to do his homework, so the former is more likely.
** The narrator of "I Don't Brush My Teeth" mentions having a beard although he still goes to school to learn grammar.

There is an additional more extreme version of this where a character is forced to retake multiple years all at once; a 10-year-old being forced back to Kindergarten to relearn the alphabet. Or forcing one character to perpetually retake their current grade ending up with a 15-year-old learning about the UsefulNotes/RomanEmpire with 8-year-olds.

* In ''Manga/MyMonsterSecret'', Shimada was held back a year.

* By the end of ''Manga/{{Parasyte}}'', Shinichi loses a school year due to [[spoiler:having spent most of it hunting down the malevolent Parasytes with Migi's help]].

* In a lengthy ''Franchise/{{Peanuts}}'' storyline from 1984, Peppermint Patty was held back for failing every subject. When school resumed in the fall, her former classmates were stunned to discover they could still hear snoring noises coming from the perpetually AsleepInClass Patty's old desk, and began referring to it as "the snoring ghost." The teacher and principal finally solved the problem by moving Patty back to her old class.

* In the ''Series/{{Community}}'' episode 'Mixology Certification', Troy was revealed to have repeated fifth grade.

* Music/{{Eminem}}, who was held back three times in real life, poked fun at himself for this in "My Name Is":
-->''My English teacher wanted to flunk me in junior high. Thanks a lot! Next semester, I'll be 35!''

** Buster is (sometimes) scared that he'll be held back.

[[AC: Extreme Examples]]

[[folder:Anime and Manga]]
* Raimu-sempai in ''Manga/{{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 ''Manga/NegimaMagisterNegiMagi'' 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.
* [[OurAngelsAreDifferent Karen]] in ''Manga/MyMonsterSecret'' has been the student council president for twenty years. Although in her case, it's less because of her grades, and more because she works for the [[{{Troll}} Principal]], who has realized that she doesn't have to pay Karen if she's a student.
[[/folder]]

[[folder:Comedy]]
* Creator/JeffFoxworthy includes in his routines,
-->"If your dad walks you to school because you're in the same grade, you might be a redneck."\\
"If you missed fifth grade graduation because you had jury duty, you might be a redneck."
[[/folder]]

[[folder:Comic Strips]]
* Calvin from ''ComicStrip/CalvinAndHobbes'' is often in danger of this due to his poor grades, but two examples especially stand out.
** In one strip, Calvin's dad finds him not doing his schoolwork, and Calvin claims to be visualizing it. Calvin's dad then tells him to imagine being the only 40-year-old in first grade.
** A variant comes up in another strip. Calvin says that he doesn't feel like going to school for most of the year for various reasons, and concludes that there would be only two days per year he'd feel like attending. They discuss what it would be like if Calvin got his way and only had to attend for those two days, and Hobbes concludes that Calvin would be a very old man by the time he got to second grade.
[[/folder]]

[[folder:Fan Works]]
* Exaggerated in the ''Literature/TheBabySittersClub'' fanfic [[https://www.fanfiction.net/s/2177005/1/Caludia-Keeshi-Middel-Skol-Mamma 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'). [[spoiler: 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.
[[/folder]]

[[folder:Films]]
* From ''Film/BetterOffDead'':
-->'''Charles De Mar''': Lane, I've been going to this high school for seven and a half years. I'm no dummy.
* Micah in ''Film/EasyA'' 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 ''Film/AFairlyOddMovieGrowUpTimmyTurner'' as a way so he can keep his fairies since if he still acts childish, then he won't have to lose them [[spoiler:(That is until the PowerOfLove 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).
* Invoked by ''Film/VanWilder'' who is deliberately repeating his last year at Coolidge College for the third or fourth time in fear of not adjusting to post-grad adult life. In the meantime, he developed a rep on campus for being FunPersonified, quite the ChickMagnet, and just an all-around NiceGuy.
* ''Film/ProblemChild 2'': Murph has been at the school for at least as long as his long-suffering teacher. He's practically an adult.
--> '''Murph''': I'm senior student in this school.\\
'''Junior''': No shit, you've been here since 1970.
[[/folder]]

[[folder:Literature]]
* Lavan in ''[[Literature/HeraldsOfValdemar Brightly Burning]]'' not technically being dropped back a few grades, because it's implied he was home-schooled before being sent to the BoardingSchoolOfHorrors. But he ''is'' placed with much younger students based on his prior education.
** Briefly discussed in ''Exiles Honor''. Alberich, despite being a man grown and at least in part ''because'' of being a captain in the Sunsguard of Karse when he was [[KidnappedByAnAlly Shanghaied]]*cough* Chosen, had enough knowledge gaps and [[{{Demonization}} probable internalized misinformation]] that even those who fully trusted him thought he needed a fair bit of instruction before being formally given his [[HighlyConspicuousUniform Whites]]. However when the elderly Weaponsmaster gave him the job of his Second it was decided to have him tutored after hours rather than compromise [[SternTeacher the authority needed to teach young muscleheads how to fight]].
* ''Literature/JakeAndTheDynamo'': Jake, just before graduating to high school, ends up going all the way back to fifth grade.
* Victor Tugelbend, the main character of ''Literature/MovingPictures'', starts the novel trying to stay in this state perpetually on purpose. He had inherited an overly generous educational trust fund from a relative, which pays out until he graduates or his grades drop below a B-. Since getting a B+ or above would cause him to graduate, and thus lose his gravy train and have to get an actual job, he goes to considerable effort to ensure that he gets straight Bs, and thus remain a student forever.
[[/folder]]

[[folder:Live-Action TV]]
* In ''Series/PhilOfTheFuture'' Phil is sent back to second grade to gain legible handwriting, because by the time the Diffy family came from, [[NoPaperFuture handwriting is essentially obsolete]].
* A non-literal example with Johnny in ''Series/TwinPeaks'' 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 ''Series/MrYoung'' episode had a scene which shows Slab graduating high school while in his 70s at least.
* ''Series/{{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 ''Series/{{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 ''Series/DueSouth'', 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.
* In ''Series/HighAndLow'', Oya High is almost completely comprised of guys in their mid-20s. How? They all ''held themselves back'' so that they could stay in the gang. {{Lampshaded}} when another character asks them how dumb they are.
* In ''Series/ElChavoDelOcho'':
** A common gag involves Don Ramón saying that he was at school for 9 years, then Chilindrina comments "Eight in first grade, and one in second".
** In one episode, Don Ramón is assisting Profesor Jirafales' class, at first as an excuse to escape from Doña Florinda, later, she and Profesor Jirafales agree to allow him in class, as he could use some good education.
[[/folder]]

[[folder:Music]]
* Music/{{Eminem}} alludes to this in "My Name Is":
-->''"My English teacher wanted to flunk me in junior high\\
Thanks a lot; next semester, I'll be 35!"''
[[/folder]]

[[folder:Video Games]]
* It's implied in the vid comics for ''VideoGame/RatchetAndClankUpYourArsenal'' that [[TheDitz Captain Qwark]] had been held back in 9th grade. And he was still there at age '''26''', when he served as TheBully to a 15-year-old [[BigBad Dr. Nefarious]], apparently causing the latter's StartOfDarkness.
* Daidouji from ''VideoGame/SenranKagura'' has been deliberately refusing to take her graduation exam, causing her to repeat the 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, which is hard because she has been assumed to be KIA. [[spoiler:In her side story in ''Shinovi Versus'', she finally gets her chance to defeat the still alive Rin, allowing her to graduate]].
[[/folder]]

[[folder:Visual Novels]]
* Amane in ''VisualNovel/IfMyHeartHadWings'' deliberately refused to graduate for almost ''ten years'' because her high school was a special engineering school that boasted great facilities, which she needed to produce the glider she had been working on ever since making a close friend as a teenager there.
[[/folder]]

[[folder:Web Animation]]
* This trope is the main plot of a category of Website/GoAnimate "Grounded" videos, wherein usually one, two, or more students start out in the 12th grade and keep knocking themselves all the way back to preschool before being expelled and sent home ([[OncePerEpisode with]] [[YouAreGrounded predictable results]]) by getting themselves in trouble by injuring a classmate or teacher, being disruptive, and/or merely making someone mad.
[[/folder]]

[[folder:Web Original]]
* ''WebVideo/DisRapsForHire'': In one season 2 episode, [[BullyHunter Epic Lloyd]] targets Diamond, a school bully who was 16 years old at the time but still in K-8 school:
-->''"You should try to pass class a little faster, guy\\
You should not be able to drive yourself to junior high\\
You're 16, dumbass! Still in 8th grade?\\
At this rate, you'll be 24 before you graduate!"''
[[/folder]]

[[folder:Western Animation]]
* In ''WesternAnimation/TheEmperorsNewSchool'' It was discovered that Kuzco did not complete his requirements for Kuzcogarten, and he was sent back there to complete them.
* ''WesternAnimation/TheSimpsons'':
** 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 RuleOfFunny.
*** Similarly, Nelson appears to be a case of this, being in fourth grade with Bart:
----> '''Nelson''': Yup, I've been held back more times than I can count. Which is probably why I've been held back so much.
** In the episode "Bart Gets an F", Bart has an ImagineSpot of him in his 30's or 40's, still in 4th grade alongside [[GenerationXerox 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 SuckySchool, 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 [[BreadEggsBreadedEggs special ed kindergarten class]].
* In the ''WesternAnimation/MyLifeAsATeenageRobot'' episode "I Was a Preschool Dropout", Jenny's sent to kindergarten because despite being, well, [[ExactlyWhatItSaysOnTheTin a teenage robot]], she was built only five years previously. She eventually gets out of it on a technicality when her creator/mother, Dr. Nora Wakeman, explains that while Jenny may, chronologically-speaking, be only five-years-old, [Dr. Wakeman] had ''designed'' [her daughter/creation] to be a teenager.
* In a TV-era ComicStrip/{{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 [[ExactWords went through all grades]] [[WillNotTellALie in one day]].
* ''WesternAnimation/FamilyGuy'':
** 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.
* ''WesternAnimation/MyLittlePonyFriendshipIsMagic'': In [[Recap/MyLittlePonyFriendshipIsMagicS2E3LessonZero "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.
* In one episode of ''WesternAnimation/FanboyAndChumChum'' it's revealed that after Fanboy sneezed on another student's placement exam, rendering it illegible, she was sent back to kindergarten.
* An episode of ''WesternAnimation/BeavisAndButthead'' called "Held Back" had the boys be continuously demoted due both to stupidity and poor social skills. [[StatusQuoIsGod They end up back in high school because the Kindergarten teacher refuses to put up with them any longer]].
* More ''WesternAnimation/{{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 ''WesternAnimation/WhatACartoonShow'' short ''WesternAnimation/LarryAndSteve''. At one point, Larry mentions that he spent twelve years in kindergarten, but he insists it wasn't because he was stupid. He simply [[DistinctionWithoutADifference got his foot stuck in a radiator]].
* Implied in the case of Brick Flagg from ''WesternAnimation/KimPossible'', 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 [[UpToEleven seven times to graduate]].
* In the ''WesternAnimation/CowAndChicken'' episode "The Bad News Plastic Surgeons", Chicken is chosen to help his school win plastic surgery events. When faced against the champions of plastic surgery (who are clearly full-grown adults), Chicken asks how they could be so good at plastic surgery and still be in elementary school. The Red Guy explains that while the plastic surgeons are great at plastic surgery, they're terrible at math.
* The ''WesternAnimation/WhateverHappenedToRobotJones'' episode "Scantron Love" had a scene where several students at Polyneux Middle School complained about how hard the Scantron tests are. Among them is a grown man claiming that he had to retake the test 137 times.
* ''WesternAnimation/KickButtowskiSuburbanDaredevil'' faced the possibility of being held back in one episode. The horror of this possibility results in him having an ImagineSpot where he sees himself as a senior citizen still in elementary school.
* In ''WesternAnimation/ClerksTheAnimatedSeries'', Jay is 26 and still in fourth grade.
* Harold in ''WesternAnimation/HeyArnold'' 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. Torvald is also 13 and in the same 4th grade class as the other main kids. He starts off as a bully but after Arnold helps tutor him at math with positive results, he becomes a lot nicer. In a later episode, he joins the kids' football team against the 5th graders because he's technically a 4th grader despite Wolfgang's protests.
* In the ''WesternAnimation/TeachersPet'' HalloweenEpisode "Costume Pity Party", the bully Dutch Calenza is implied to be an adult who has been held back in school, considering how much bigger he is than the other students at school, his gruff voice provided by Creator/BradGarrett and his revelation that he was picked on for [[DiscoSucks dressing as a disco dancer]].
* In ''WesternAnimation/AmericanDragonJakeLong'' local JerkJock and BookDumb Brad Morton has been held back at least twice as he bragged to Jake and friends that he was old enough to get his driver's license in one episode and in another announced that he had just done the "Bradster's" ''fourth'' annual eighth grade prank on his middle school's principal, making it uncertain just ''what'' his age actually is beyond being at least sixteen.
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