History JerkassWoobie / Film

* Sean in ''Film/Alaska''. Sure, he’s an insufferable asshole, but consider that he’s had to deal with the recent death of his mother, and he is having to adjust to a new home while he is still in mourning, it’s hardly inexplicable.

* Amber Von Tussle from the 2007 adaption of ''Film/{{Hairspray}}''. She may be an bratty AlphaBitch, but at the end of the movie, [[spoiler: she loses her crown to a child and her boyfriend. She also falls from a set hard enough to hurt her ankle. She then talks coyly with a black dancer, implying a HeelFaceTurn.]]

*** The Daniel Craig version of James Bond is pretty much a ByronicHero who [[ParentalAbandonment is orphaned at an early age]], [[PerpetualFrowner generally looks unhappy even when he smiles]], [[KnightInSourArmor has a grim outlook on his job]] and [[HurtingHero still regrets losing his loved ones and allies]], especially [[TheLostLenore Vesper Lynd]] in ''Film/CasinoRoyale2006'', [[CoolOldGuy René Mathis]] in ''Film/QuantumOfSolace'' and [[ParentalSubstitute M]] in ''Film/{{Skyfall}}''. On top of this, [[ParentalSubstitute his adoptive father]] was killed off by his own [[BigBrotherBully foster brother Franz Oberhauser]], just because Bond got [[CainAndAbel more endearment]] than him, and [[DisproportionateRetribution is bent on making Bond's life miserable in any way possible]].

* Raymond Shaw from ''Film/TheManchurianCandidate''. Yes, he's a cold, misanthropic jerk, but judging from what's implied about his childhood, it'd be amazing if he weren't. And that's not even counting what he goes through over the course of the film. The only two people he's ever truly cared for are Major Marco and Jocie, and his mother brainwashes him into killing the latter. The universe just hates this guy.

* Lee Woo-jin in ''Film/{{Oldboy 2003}}''. Sure, he is the king of DisproportionateRetribution and a manipulative, sadistic, ruthless, evil man, but still, many viewers will say that [[spoiler:his flashback to his sister's suicide]] is the most heartwrenching scene in the movie.

* Harry from the first two ''Film/HomeAlone'' films and the hotel concierge from the second film. Harry is a hot-tempered burglar who [[spoiler: tries to bite off Kevin's fingers in the first film and tries to ''shoot'' Kevin in Central Park in the second film]] but considering all the sadistic and nasty things Kevin does to him(and Marv), especially in the second film, few people wouldn't feel sorry for him. The concierge in the second film, meanwhile, is [[InspectorJavert a little overeager to bust Kevin for "credit-card fraud"]] and is an all-around smarmy jerk but watching him get outsmarted and humilated by Kevin, and later slapped in the face by Kevin's mother, makes him pitiable.

* ''Film/BuffaloSixtySix'': played to the hilt with Billy Brown. He's a total jerk, braggard, liar, and kidnapper, but only because he's led such a humiliating and pathetic life, in part due to his absentee parents.

* ''Film/{{Valentine}}'':[[spoiler:Jeremy Melton is a ruthless SerialKiller in the present day, but one can feel sympathy for how he turned out, given that he was framed for sexual assault before he'd reached his teen years and his life essentially ruined. In his own words, what he suffered became too much for him to handle and the only recourse was taking revenge on the people who put him there. He also has a soft spot for his girlfriend Kate, [[BecauseYouWEreNiceToMe who was kind to him even though she rejected him]] and was the only member of the GirlPosse who didn't corroborate the frame job, even taking time to murder a man who was stalking her.]]

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* ''Film/NotOkay'': Done purposefully with Danni who is effectively made to be both unlikeable and at the same time pitiable to emphasize the problem with cancel culture. While her actions are absolutely deplorable, the backlash she receives ends up being disproportionate, varying from people accosting her in stores, sending death threats to her and her family, and posting her home address online. All the while she was a lonely and depressed young woman who went from being ignored to being the most hated person in America with people calling her worse than Hitler.

* Luke from ''Film/Cherrybomb2010''. While he undeniably behaves like a Jerk on several occasions, he does have a huge FreudianExcuse - he suffers appalling abuse and neglect at the hands of his family - and is clearly very emotionally vulnerable. The fact that he's tall, dark, and {{Bishonen}} (i.e. the fact that he's played by Creator/RobertSheehan) probably doesn't hurt either.

* Luke from ''Film/{{Cherrybomb}}''. While he undeniably behaves like a Jerk on several occasions, he does have a huge FreudianExcuse - he suffers appalling abuse and neglect at the hands of his family - and is clearly very emotionally vulnerable. The fact that he's tall, dark, and {{Bishonen}} (i.e. the fact that he's played by Creator/RobertSheehan) probably doesn't hurt either.

* Teddy Duchamp in ''Film/StandByMe'' is still the most unstable of Gordie's friends, but has the less pleasant qualities of his craziness toned down compared to his book counterpart. He also [[spoiler:doesn't get himself and some other buddies killed in a drunk driving crash later in life]].

* The title character in 1981's ''Film/{{Arthur}}'' is a downplayed example. He's a devil-may-care millionaire alcoholic playboy nonetheless prone to self-pity regarding his loneliness, desperate to avoid taking on adult responsibilities, and annoying to most of the people around him because of his constant joke-cracking. But beyond the fact that he '''is''' a LonelyRichKid, he has a generous heart capable of great love, he jokes to make people happy, and he really is funny -- it's just that most of the people around him are terminally humorless. In-universe Hobson, his valet and the one person in his immediate circle who truly loves him, sees him as this and goes on to help Arthur find true love -- and a little maturity -- with a working-class woman who appreciates his good qualities.