Similar to Hollywood Homely and Hollywood Dateless, and typical of High School shows, this is when a character who is smart, funny, fashionable and good looking is portrayed as being much less popular than they would be in real life. Done deliberately to limit the circle of friends/cast as much as possible, thereby erasing the hassle of writing multiple, varying characterizations, while at the same time making the main character likable to the viewer. If this character is female, she is frequently a target of the Alpha Bitch.
Unlike people who are Hollywood Homely, Cool Losers are not supposed to be considered unattractive, and unlike the Hollywood Nerd, the Cool Loser is not a geek or lacking in social skills. They just don't have many friends, don't get invited to the cool parties, and are generally treated like losers by most of their peers.
This often leads up to a big payoff, when the Cool Loser is briefly given a moment when they realize that more people do, in fact, like them than they thought (usually when they are unexpectedly honoured at some manner of ceremony, such as a graduation). It's not explained why those honouring didn't demonstrate this in some way earlier, but it often comes in the form of a sweet gesture.
Often overlaps with This Loser Is You. See also Hollywood Nerd. An Informed Loner is basically this, except they supposedly don't even want friends.
Examples:
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Anime and Manga
Minako in Sailor Moon seems to be a victim of this; unlike the other girls she lacks any other obvious traits that would make her unpopular. It's likely The Artifact from working solo in her own comic to being retrofitted into the new storyline, as she originally started out as an admiration object turned comedically Broken Pedestal.
Eikichi Onizuka of Great Teacher Onizuka is pretty cool and a pretty big loser at the same time. He used to be in a gang, he rides a motorcylce, he breaks things... but he's never had a girlfriend, cosplays during class, and is so broke he doesn't even know who's on the 10,000 yen bill.
Kyoya Hibari from Katekyo Hitman Reborn!. In character polls, he has consistently been rated as the fan favorite and the hottest guy in the series, and was ranked #1 within the top 10 for "Anime guys you would marry". Yet in the series itself, no one has taken any semblance of romantic interest in him (save a 1-year-old child, and even then, it had to be explained that she only had a crush on him because he looked like her teacher). He's a Jerk AssBlood KnightAloof Ally that is only a member of the Five-Man Band due to a loose connection to the 1st Cloud Guardian that he resembles. And that didn't stop the girls in the school from swooning over him. Not to mention he's uber powerful and strong, and most likely very rich.
Taikoubou from Houshin Engi. He's an adorable, hilarious, good-hearted, young-looking immortal that's insanely smart, and manages to come up with genius tactics to save the day. Yet absolutely no halfway decent women have any romantic interest in him throughout the entire series... save for a hideousGonk that disgusts everyone (including and especially him). Sure, he's an asexualCelibate Hero that has no interest in romance... but it's not like he's always announcing it and letting everyone know, and there's no real reason why no one is interested in him.
Peter Parker is (to the reader) a handsome, highly intelligent, funny guy who used to be Happily Married to a stunning red-haired supermodel, and now is a relatively successful freelance photographer. In real life, he'd be amazingly popular...most likely One of Us. In Marvel Universe Manhattan, though, he's all but completely ostracized from his peers because...well...he's Peter Parker.
Film
A Cinderella Story. You're telling me Hilary Duff is the school outcast?
Possibly justified. The two stepsisters probably take steps to make sure that she remains unpopular.
Justified in Mean Girls - Janis Ian is good looking, smart and funny but her reputation was destroyed by a rumor and she now willingly embraces outsiderdom. (Also averted by the protagonist Cady who quickly becomes popular and powerful to the point that she can become the new Alpha Bitch).
Producers were actually reluctant to cast Lizzy Kaplan as Janis because they thought she was too pretty for the role. They settled by giving her a goth/alternative look that would justify the popular girls avoiding her.
An adult example: Jim Carrey's character in Bruce Almighty is allegedly a loser ... even though he works as a TV reporter and his girlfriend is played by Jennifer Aniston. Played with in that one of the film's key themes is how unappreciative he is when he actually has a good life - he sees himself as a loser, but hardly anyone else does.
Michael Cera and Jonah Hill's characters in Superbad. An attractive girl clearly has the hots for Cera's character, and they're both invited to the hip party at the end, yet they're under the impression that they need to bring a ton of booze for any of the girls to get with them.
The Trotsky has a classic instance similar to the Mean Girls example above: Leon's two friends in the student union who become his main supporters are a gay guy and an alternative-looking girl who are first shown smoking pot together. They are clearly unpopular despite being shown to be intelligent, driven, and funny by the end of the movie. Leon himself may also qualify, but this is justified in that his insane obsession with his namesake would understandably make him an outsider.
Ho's Rohit Patil, who happens to be the rich and good - looking (as well as funny and sensitive), is introduced as unsuccessfully flirting with three different woman
Booger in Revenge of the Nerds, to the point where his actor, Curtis Armstrong, often asked why Booger was in the nerds group at all.
Literature
J. K. Rowling even makes a few stabs at this in the Harry Potter series. Harry's famous, a pretty nice guy, and is regarded as a hero. Yet in Chamber of Secrets he's ostracized because he can talk to snakes, in Goblet of Fire he's ostracized for entering the Triwizard contest ("Harry is a cheating cheater!"), and in the next book he's looked down on because he's the only one who notices there's a frickin' war going on. In the sixth book, he does become hugely popular, but finds it annoying.
Ron fits this trope even better than Harry. By the age of 13, he's helped Harry defeat Voldemort (in one form or another) twice, and has been given an award for special services to the school. He's a Deadpan Snarker who's best friends with the Chosen One, his brothers are all ultra-cool (Except for Percy. Nothing can make him cool), and it's implied that he's at least moderately attractive. While he isn't a straight-A student, he's not described as stupid by any measure. And he fights a bunch of adult Death Eaters, and becomes star player in a cup-winning House Quidditch team. He's still not treated as particularly cool though. Apart from Harry, Ron should be the most popular kid in school among everyone but the Slytherins.
Explained by Hermione in Goblet of Fire that Ron gets pushed off to one side in favour of Harry because of Harry's fame. Besides the other students in their year who have classes with them and some friends of Ginny's, no one spends enough time with Harry or Ron to realise that Ron is cool, too - they're just in awe of Harry.
Perry Mason. His only admirer is his secretary, Della Street. This one especially boggles the mind, considering that he's an incredibly rich, handsome, powerful, world famous lawyer that is well known for being on the side of justice. He has hundreds of attractive, young female clients, who go through life and death situations with him, where he's always there to comfort and save them in their time of need. Yet none of them ever fall for him. If they flirt with him, it's always because they're just trying to manipulate or trick him. Apparently, no woman during those days wanted to chase and marry an insanely rich, prominent lawyer.
The Eerie Indiana books attempt to justify this: the charming but unpopular town bum, liked only by the main characters, used to be the mayor before he irritated a witch.
In Maggie Furey's Shadowleague books, it's mentioned that Kazairl and Veldan were seen as this when they were young in Gendival.
The entire main cast of Stuck, Tre, Allie, Nora and Max being the largest examples.
Live Action TV
Completely parodied in an episode of Seinfeld, wherein Jerry dates a girl who seems to be perfect (smart, attractive, funny, friendly) but is ostracized by her own friends. Later, even Kramer and George sit Jerry down to tell him he can do better (heavily implying there is something very wrong with this girl), despite her obvious positive and desirable attributes. Everyone but Jerry seems able to tell this girl is a super loser in some way (which they never clarify), so he puts her to the ultimate test, meeting his parents. They love her and he immediately begins to think poorly of her as a result. What exactly people were seeing wrong with her is never explained.
Buffy in Buffy the Vampire Slayer, although she was initially accepted by the in-crowd before her Slayer duties led them to disowning her. In the end, she only really had two friends at school - Xander and Willow.
In "The Prom", however, Buffy receives a special Class Protector award for saving the other students' lives on a regular basis.
Sabrina in Sabrina the Teenage Witch: Despite being an attractive do-gooder and a model student, she was treated with contempt by both Libby and Vice-Principal Kraft. Libby at least might have seen Sabrina as a threat to her own popularity, but Kraft... well some people are just jerks. That and he dated her aunt.
And then he dated the other aunt. Poor Sabrina...
Aside from just plain being evil, Libby hated Sabrina because she was jealous of her. She tried many times to steal Sabrina's boyfriend, Harvey, and practically leaped for joy every time there was a chance that Sabrina didn't get a perfect grade. In the episode "When Teens Collide" after Sabrina and Libby switch pesonalities, a couple of popular cheerleaders explain to Sabrina that while everyone likes Sabrina for being nice, smart and pretty, Libby is popular because everyone fears her.
And regarding Mr. Kraft, while part of it may be bitterness after getting dumped by Sabrina's aunt, there's the possibility that before that it was due to her position with the school newspaper. Football players and cheerleaders (the people Kraft cozies up to) bring in a certain amount of revenue to the school, through ticket sales, concessions, and possibly donations (if it's that type of school.) School newspapers are often free to students and expensive to produce, so Kraft might see it as a giant money pit, and decides to take it out on Sabrina.
Samantha from Popular: Despite being gorgeous and smart, she was unpopular. A snarky recapper on Television Without Pity actually pointed out that for all her supposed outsiderness Sam generally had more stylized hairstyles and make up than the actually popular Brooke who looked like she just ran a comb through her hair every morning.
Seth Cohen is clearly an attractive, talented, funny and ridiculously rich young man, yet he couldn't get a date for most of his life, despite living in a town full of golddiggers, and was constantly being beaten up by jocks. Not only this, unlike the majority of examples on this list he apparently had no friends at all prior the arrival of Ryan.
It's implied that Seth would probably be popular if he lived anywhere besides Orange County. This is particularly obvious when he briefly moves to Portland, and apparently has no trouble making friends. It's just that he's surrounded by people who are pompous and shallow. There is also a suggestion that he can be slightly self-centred and petty despite himself sometimes.
Taylor Townsend, a stunning, whip smart, witty young lady who is so unpopular she is reduced to following around Seth (and Summer) for want of a friend. Granted, her well meaning but hyper personality might be a little hard for some to take...
Veronica Mars: The lead character is witty, attractive, fashionable and generally benevolent. Veronica's unpopularity is ostensibly due to her father's insistence that local hero Jake Kane was a murderer. It wasn't until later on, when she becomes more than a little infamous for her ability to figure things out, that she regained some respect — her 10-Minute Retirement at the beginning of the second season proves that.
Once again, Buffy-style, at the end of the second season, she's given a minor ovation from her classmates as she accepts her diploma.
Wallace Fennel, Veronica's best friend is also an example of this. He's at best marginally popular, despite being the star on the basketball team, very nice, funny and dating the super hot daughter of a baseball legend.
In Veronica's case, it's arguably on purpose. She's pissed at them for essentially abandoning her when she needed her friends the most. The ones she eventually forgives are generally the ones who had their own issues regarding Lily's death (Logan and Duncan are pretty much the list). The theme song was well-chosen.
In Wallace's case, it's at least partly intentional. As he said, he'd rather hangout with the chick who cut him down when duct-taped to the flag pole than the people who just stood and laughed at him.
Dawson's Creek: Almost all of the attractive major characters are depicted as being stereotypically uncool, particularly the beautiful and intelligent Joey.
To be fair, Joey's unpopularity is often shown to stem from her poverty (at least compared to the other characters), the scandal of her father being in jail for dealing drugs, and the fact that she clearly holds the entire high school social structure in contempt.
Clark Kent from Smallville: played by an underwear model, became a football hero, occasionally works at school newspaper, and is friends with the multi-billionaire Lex Luthor (who himself is popular), yet is still viewed as a loser. This also extends to Chloe Sullivan who, despite being a very attractive blonde, head of the school newspaper, and sporting enough popularity to become Prom Queen, is still looked down upon by the Alpha Bitches. This is probably due to the Wall of Weird and frequently exposing liked people.
Except that Clark was never stated to be unpopular, he just prefers to keep a lower profile than many. In the first season Pete even mentions his popularity as a reason why he would be good as class president.
Chloe also gets a bit of what's due to her when Jonathan Taylor Thomas' character refers to her and Lana equally as "the two hottest, smartest girls in school".
Chloe is actually something of a subversion. In the Prom episode, it's revealed that Chloe is actually a lot more popular than she realizes. It turns out that although Chloe is well-liked, the resident Alpha Bitch and her Girl Posse hate Chloe's guts because of the fact that Chloe holds their social structure in contempt and arguably because Chloe's reporting work at the newspaper (which they seem to really despise) resulted in several members of the popular clique being jailed or institutionalized ever since Season 1, and they refer to Chloe's paper as a "geek rag." Meanwhile, when Clark secretly nominates Chloe to be Prom Queen, it turns out the Silent Majority of Smallville High students had secretly been rooting for Chloe as sort of a hero to the outcasts of the school. Indeed, Clark actually says "Everyone's been trying to break out of the stereotypes that they've been forced into...and you're the rallying cry."
Freddie on iCarly gets this, whilst Carly does not. Sam appears to be feared more than respected, so is similar to Carly, but in a different way.
There's actually some discussion that Carly actually does suffer this whilst the other two don't. Sam has shown to be involved with a gang of troublemakers, and Freddie has about a dozen clubs that he gets kicked out in iMeet Fred that he arguably gets back in eventually, whilst Carly has nothing. She was shown studying with Wendy once and Gibby is the only one apart from Carly and Sam that has regular contact with her.
Miley's alter-ego on Hannah Montana, and her best friend Lilly. Both are self-professed "losers", even though they have the social skills and good looks to be popular (and, in fact, in an "alternate timeline" episode where Miley never met her, Lilly has become the school's Alpha Bitch). One can only assume that Miley is purposefully pretending to be mediocre in an effort to better disguise her pop-star persona. When she is being Hannah Montana, she has a robust social life and frequently attends large parties. This still doesn't explain Lilly, though. (On the other hand, the third part of their trio, Oliver, is the epitome of social awkwardness... perhaps hanging out with him is enough of a social blight to bring Miley and Lilly to the bottom.)
Miley was the new kid, and her Southern accent turned people off. Lily is only unpopular because she goes out of her way to be Miley's friend (since she is also a decorated athlete and even a cheerleader.) Oliver is more popular in later episodes, even though he became annoying beforehand. Initially, when he was nice, he was this trope.
In early episodes at least Lilly is portrayed as a sk8tergirl tomboy.
Claire's friend Zach on Heroes. Justified in that the student body seemed to regard him as homosexual, and this was a bunch of high school students we're talking about.
Lizzie McGuire and her friends are considered losers. Roger Ebert makes a crack at this trope's expense, wonder how a girl whose smile "shines brighter than all the stars in the sky" could be unpopular.
Julie from Sorority Forever. This may be justified by the fact that Bridget, the head of Phi Chi Kappa, takes a disliking to her for her rebellious and inquisitive tendancies.
Boy Meets World's Cory Matthews. This guy lives and breathes this trope.
Kerry from Eight Simple Rules is intelligent, artistic and attractive - a bit snarky perhaps, but for some, that's part of the charm. Still, she's generally portrayed as less desirable than her older sister Bridget.
Justified in the first season because she's moody and condescending as well as being a little bitchy. She actually becomes more popular than her sister at the start of season 2.
Played with in Wizards of Waverly Place in that Alex seems to deliberately seek out this status.
In fact, it seems to be a staple of Disney Channeloriginal movies, glaringly so in Alley Cats Strike, wherein the otherwise cool captain of the school bowling club is regarded as some sort of misfit outcast (that is, until the movie's main events kick into gear).
This isGlee. Everyone in the Glee Club is automatically unpopular for being part of it, even though three of them are cheerleaders, several of them are on the football team, and the rest are just pretty friendly. They just seem pretty fun and cool and yet everyone seems to dislike them. They'd probably be popular in any other high school!
As of season two the entire club is/has been on the cheerleading/football team or dating somebody who is. Logically, these are the most popular people in school. It makes the whole "We're all misfits!!" thing hard to swallow.
In the episode "Original Song," the Glee club, minus Rachel, write a Cool Loser anthem for New Directions appropriately called "Loser Like Me."
Then again, it's mentioned for Rachel specifically that she's so insanely annoying that she's an outcast. Kurt's the Camp Gay in a small conservative town in Ohio, Tina goes out of her way to avoid people, and Artie's in a wheelchair which he even admits puts a lot of people off.
Which explains those four. The rest of the club are perfectly relatable and unrealistically good looking.
On two occasions, they have elicited practically a cheering riot from the assemblies they perform at. Yet no one except hecklers show up to the concert that they put together in "A Night Of Neglect."
This may actually be a Deconstruction as it is shown that the members are rather regular people. The only reason they're unpopular is because they're in Glee club, so it's less their own fault and more like the school's shallow outlook.
Lance Stone from Dark Oracle although this is at least partially deliberate on his own part. He's capable of being socially functional, but his interests in role-play and video gaming, combined with an antisocial streak and the fact that his girlfriend, Sage is one of the most picked on girls in the school keep him pretty isolated.
Mia Jones from Degrassi is the would-be spicy cheerleader but being a teen mother stands in the way until she becomes a model.
Jenna Hamilton on Awkward.. The whole series could be summed up as a Cool Loser realizing how cool she actually is.
You forget to mention: he's an Otaku. Watch the cool meter drop right to past zero.
He fits the trope (jobless, only one friend), but the only opponent of his that disrespects him is Destroyman, for reasons not related to his social status. Most of the blatant disrespect that we see comes from Silvia and Naomi, the former of which is more than just kind of a bitch to begin with (with tones of the Alpha Bitch) and the latter of which a bit of a grouch and jerk in her own right.
He's also very well respected by basically everybody in No More Heroes 2: Desperate Struggle, to the point of idolizing. He even gets a couple of fangirls.
His situation in the sequel can probably be explained as people knowing more about Travis' reputation than Travis himself. The game's opening narration basically says that Travis has become something of an urban legend. They don't so much idolize Travis himself, but the person who climbed to the top of the UAA rankings that fast and walked away, a person who just happened to be Travis Touchdown.
Reimu Hakurei of Touhou. She is shunned by basically everyone, the only human to give her the metaphorical time of day being fellow outcast Marisa, and the only youkai being Suika (who mooched off of her for a while) and Yukari (who views her as an asset). This is despite not only being rather amicable (at least by Gensoukyou standards), but also saving everyone's lives at least twice and essentially being the only thing stopping the more powerful individuals from doing whatever they please.
Theater
Cyrano de Bergerac: Even when this play is not settled in High School, the Gascons are the Cool Losers that de Guiche, the Jerk Jock, is trying to pick on with help of his Girl Posse, De Valvert. The Gascons are all proud of being losers and of being cool.
Web Comics
Jodie from Loserz. Sexy, a good artist, funny, but most people except the protagonists only want to have sex with her, or actively hate her. Of course, the girls mostly hate her because she sleeps with their boyfriends...
Mike Cosley from Bardsworth was one of these in high school. When he gets to college (magical college, at that), he's not as actively mocked as he was, but he isn't exactly Mr. Popularity.
Candi from the Ciem Webcomic Series may be really pretty and all, but the town of Viron just gets a real thrill out of being very abusive to her. While she is a closet nympho, she does her best to control her urges, and keeps her releases restricted to her monogamous relationships. Still, she gets treated like a slut frequently, by those who would have no way of knowing anything about her actual level of experience. Given that some of the region's residents are clearly Brainwashed by the Hebbleskin Gang, Candi has an excuse to not want a whole lot of friends.
Web Original
All of Team Kimba (the protagonists) in the Whateley Universe, even though the group contains some of the hottest girls(-ish) on the entire campus. One of them is regarded as possibly the hottest girl on the planet (she's part Sidhe and has a Faerie glamour). They live in the dorm that's regarded as the campus loonybin (it's not). Before their mutant manifestations, many of them were 'losers' for one reason or another.
Western Animation
Ron Stoppable from Kim Possible is certainly one of these. He's not stupid, he's not a clutz, and he doesn't lack in social skills. He's often confident and he knows how to pick up the ladies. (They just reject him anyway). He's just a bit of an idiot sometimes.
Timmy Turner of The Fairly OddParents starts out as a loser but eventually manages to gain quite a status in the eyes of his peers as the series progressed, unfortunately turning him into an inflated Jerkass. Granted he does temporarily degrade back into a Cool Loser whenever the plot or humour calls for it.
In Danny Phantom, while Tucker and Sam fit the bill, Danny seems to be bigger loser than both put together for no other reason than the sake of it. That and to allot for a lot of scenes with the Jerk Jock/school bully. His parents' reputation as loony ghost hunters may have something to do with it, initially, but that excuse goes right out the window as soon as ghosts become a genuine threat to the town.
Actually Danny becomes more and more popular subtly as the seasons progress; girls are willing to talk to him and express interest in him. So while he isn't seen as popular later he isn't shown as as much of a loser.
Considering how Danny's parents would mainly go after ghosts by crashing around while shouting and waving around strange devices, it's not that much of a stretch to imagine that - ghosts or not - Danny would be laughed at.
And...Danny is pretty shy early on in the show, or not all that great at communicating when he's not with his close friends. That would definitely lead to being called a loser by impatient and very outgoing teenagers like those of the A-List.
In the never-picked-up Crash Nebula, the main protagonist is just as surprised as the viewer when he is informed of his immediate loser status.
Arthur from Shrek The Third seems fairly normal, maybe a bit introverted, but he's picked on by everyone, including the stereotypical DnD nerds.
In "They're Playing My Song", Richie and another African-American kid were laughing together at Virgil while he was working at Burger Fool. Maybe he's another friend of Virgil, Richie, and Frieda.
Of course, there's the fact that Virgil's secret crimefighting life puts a fairly huge dent in his free time. Given that, it's probably justified that he'd only be able to hang out with his closest friends (one of whom is in on the secret and joins him as a Bang Baby hero later.)
Optimus Prime suffers from this in Transformers Animated. While on Earth he's viewed as amazingly cool and a hero, on Cybertron he's a loser and a nobody - his only defining feature there being that he's in charge of other losers, dropouts and failures. This does nothing for his self-esteem.
Somewhat justified in that the only other Autobots who even seem to know what Optimus and co. have been up to either think it's best to keep the whole issue of Earth in the background (Ultra Magnus) or hate his guts (Sentinel Prime). Even if word did get out, who would believe that a nobody commander in charge of a maintainance crew went up against Megatron and not only lived, but won? TWICE?
On Teen Titans Beast Boy is a superhero who's helped save the city hundreds of times, but whenever we see him interacting with anyone who's not a Teen Titan, he gets treated like crap. Of course, people in the Teen Titans universe seem pretty blase about the whole superhero thing in general, since the Titans can go to a pizzeria in full costume and no one bats an eye.
The whole thing with Beast Boy may be the fact that he is in fact deeply insecure and tries to hide that insecurity with humor which most of the world, including other Titans, rarely seem to get.
