Let It Ride. Jay Trotter (played by Richard Dreyfuss) is practically the Trope Codifier. As the movie tagline states: "He drinks. He smokes. He gambles. He curses. He thinks about committing adultery. You'll love him." His best friend Loomey is even more of one.
Effie White from Dreamgirls. She started out as pushy, rude, selfish, and self-centered, but when she loses her man to her beautiful friend while she's pregnant with his baby (then he marries her eventually), and kicks her out of the group, its not hard to feel sorry for her. She then goes through Character Development.
Darth Vader in Star Wars is responsible for many of the Empire's atrocities, particularly killing the Jedi. He did so in an attempt to save his wife from dying, but this ends up happening anyway as a result of his own actions. And (he thinks) his unborn child(ren) died with her. And before that, there was his mother. Then there's the fact that the whole galaxy hates him for trying to do the right thing. Emperor Palpatine convinced him that the Jedi were trying to overthrow the Galactic Republic and sends him visions of his wife dying, so Anakin tries to save her by learning the secrets of the Sith, only to be overcome by the Dark Side. Then he ends up Force choking his wife in anger, who later dies, his best friend dismembers him and leaves him to burn to death at the end of their fight, and he had the rest of his friends either killed or driven away. The only person he has left is his worst enemy, Palpatine - who got him into this mess to begin with - until he learns that his son, Luke Skywalker, is alive. Jerkass Woobie indeed.
Joe Dick in Hard Core Logo. He can be amazingly self-centered, he's an unrepentant liar, and he gets his closest friends caught up in his self-sabotaging antics, but he obviously cares so much in his own screwed-up way that you wind up feeling sorry for him. Especially considering that he shoots himself.
Luke from Cherrybomb. While he undeniably behaves like a Jerk on several occasions, he does have a huge Freudian Excuse - 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 Bishōnen (i.e. the fact that he's played by Robert Sheehan) probably doesn't hurt either.
Inception: Mal. Yes, she ruined Cobb's life by framing him for her suicide, but this was only because she had spent so much time in the dream world that she was unable to distinguish what was a dream and what was reality. This led to her killing herself, convinced that she would wake up in reality. In the end, all she wanted was to go someplace where she could be happy forever.
Buffalo '66: 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.
Mark Zuckerberg from The Social Network. He's an Insufferable Genius who discards people when they're no longer useful to him, but one of his lawyers finds out that much of his behavior is a Jerkass Fašade, and he's actually significantly more lonely and vulnerable than he lets on.
Louis Winthorpe in Trading Places. He was a snobby Blue Blood commodities broker who ends up being framed for embezzlement and drug dealing, gets incarcerated, loses his home and wealth, and gets shunned by all his friends and fiance, who's also led to think that he's been cheating on her. The shock of all this proves so much that he gets Driven to Suicidetwice. He gets better after he learns that he went through all that because of a bet by his bosses of only one dollar, and he gets back at them magnificently.
The titular character of Hedwig and the Angry Inch is this in spades. He/She gets a botched sex change operation in order to obtain a Citizenship Marriage out of East Germany and, upon arriving in America, has to work as a prostitute to survive. She is also a snappy, bad-tempered diva who treats her band members like absolute shit - esspecially Yitzhak - which delves into outright psychological abuse at time.
Wolfgang Amadeus Mozart in the 1984 film Amadeus, a Jerkass and Insufferable Genius, with an Annoying Laugh to boot. Once he gets around to writing the Requiem Mass, though, he starts breaking down physically and mentally, and you can't help but feel sorry him.
At first, John Bender from The Breakfast Club comes off like a punk with no reason behind his behavior, but it's later revealed that he has a very bad home life stemming from his father's abuse. He doesn't really change by the end of the movie, but your impression of him is softened considerably.
Raymond Shaw from The Manchurian Candidate. 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 universe just hates this guy.
Henry VIII as portrayed in Anne of the Thousand Days. He'll do anything for a male heir, no matter how unethical, unlawful, unpopular, or uncomfortable for himself, but all he gets for many years are daughters and stillborn sons. Small wonder that after the fourth failure, he shouts, "I am accursed!" His ex-wife, as badly as he treated her, pities him.
Anne herself spends most of the time as just a Woobie, but she does insist on the execution of every cleric who doesn't recognize her marriage.
Sidney Falco in Sweet Smell of Success, largely because most people he meets seem to loathe him before he even gives them reason to (which, granted, he probably will). And because his boss, J.J. Hunsecker, is just so much worse.
From The Final: Barring Dane, all of the other outcasts(Andy, Ravi, Emily and Jack). They've been warped by years of abuse at school and unhappy home lives. Even as they torture their abusers, they want to keep the one guy who was nice to them away from it all.
Hugo: The Station Inspector. His leg was crippled in World War I, and beneath his stern, relentless persona is a lonely man who is harsh on orphans because it reminds him of the pain of being one himself.
This is a major departure from the book, in which the inspector was a stone-cold, almost antagonist. It was surprising to see him become a relatable character in the adaptation.
The Marvel Cinematic Universe version of Loki is very much this trope, both in Thor and in The Avengers. On the Jerkass side, he kills an awful lot of people, to the point that even Thor seems to consider him to be this trope. However, you can't help but feel sorry for him when it's revealed that he's actually an adopted Frost Giant and it's revealed that his main motivation is to prove to his (adoptive) father that he is a worthy son. This also overlaps with Woobie, Destroyer of Worlds.
Nicholas Garrigan in The Last King of Scotland is a conceited, ignorant and selfish individual, constantly chasing the skirts of married women. However, seeing him getting meathooks shoved through his chest and then suspended from the ceiling, does make one feel sorry for him.
Titanic: Caledon Hockley. Being a product of his times, he genuinely cannot understand how Rose could possibly be happy as the wife of a homeless man with no financial security. He is a classic Crazy Jealous Guy who treats Rose like a possession rather a person, though it should be noted that this is also a direct by-product of his upbringing and culture. Rose and Jack themselves, meanwhile, are clearly ahead of their time as far as their values go(this may explain why so many people view them as anachronistic characters). In short, he genuinely loves Rose but does not know how to show it properly, he loses her to another man, and then gets to New York thinking that she's dead.
William "D-Fens" Foster in Falling Down. A divorced husband and a violent, sociopathic Vigilante Man who took his anger out on every frustration he came across, but whose main motivation was to see his daughter.
Tyler Durden from Fight Club. He is only a split personality of the narrator and is literally the personified composite of his rage and melancholy; he hates himself, hence his pontificating about self-destruction and hitting bottom. And the narrator, the very person who created him, kills him at the end of the film. However, he is also a nihilistic sociopath.
Travis Bickle from Taxi Driver. A sociopathic, bigoted Vigilante Man who wishes to cleanse the "fifth" in the streets. But his main problems was because he was suffering from severe insomnia and depression. Not to mention that as a taxi driver, he was forced to work in the dangerous streets containing pimps, addicts and thieves.
Eddie Valiant in Who Framed Roger Rabbit. His brother's death is what turns him into an alcoholic like he was today.
Ryu, a deaf-mute aspiring artist who leave art school to take care of his ill sister, who badly needs a kidney transplant. He seeks help from the organ traffickers, out of desperation after he was fired from his job. However, they swindle him out of the money, leaving him unable to pay to the surgeon. With the help from his girlfriend, Cha Yeong-mi, he plans a kidnapping scheme. Unfortunately, kidnapping his boss' daughter would attract the attention of the police, so instead, they kidnap Yu-sun, the daughter of Ryu's boss' friend, Park Dong-jin. As things were to turn for the worse, Ryu's sister commits suicide after finding out about the scheme. In her letter, it asks Ryu to return the daughter safety to her father. Unfortunately, while Ryu was burying his sister at the river, Yu-sun accidentally falls into the river and drowns when Ryu was unable to hear her. Remorsefully, he places the little girl's dead body by the side of the river. Afterwards, he went on to get revenge on the organ dealers. His days doesn't turn out for the better, however, when while exploring Yeong-mi's apartment building, and getting into a lift; he founds his girlfriend's dead body in a stretcher. Consumed with grief, he swears vengeance on his girlfriend's killer as he holds his dead girlfriend's hand. He waited for several hours at Dong-jin's residence but to no avail. Ryu went back to his apartment, only to find that Dong-jin had managed to break into his house. In an attempt to sneak in through the door, he was knocked out unconscious by the booby trap on the door knob. He was binded by Dong-jin, then at a river where Yu-sun had drowned, have his Achilles tendons slashed, and drowns after a minute of trashing about.
Cha Yeong-mi, girlfriend of Ryu. She's a radical anarchist who suggests to her boyfriend about the kidnapping scheme. Her misery is specifically because of her cruelElectric Torture by Dong-jin. She apologizes about Yu-sun's death, then warns her torturer that she's part of a terrorist organization before she was killed.
President Park Dong-jin also counts. He was a divorced husband and a former boss of Ilishin Electronics. His daughter was kidnapped by Ryu and Yeong-mi, who asks for the ransom to be delivered. Even the director states that he was a victim of circumstances. Just when Yu-sun was about to be returned to her father, however, she drowned in the river when Ryu was unable to hear her cries for help. Dong-jin swears vengeance on the kidnappers at his daughter's funeral. After finding out about their identities, he starts by going to Yeong-mi's apartment and places her through an Electric Torture. But he also had to kill the delivery boy who deliver the noodles to Yeong-mi's house, the person whom the woman called earlier. He hears Yeong-mi's apology about Yu-sun's death, but ignored her warnings that she's part of a terrorist group, knowing of his identity, will kill him if she dies, so he kills her anyway. Later on, Dong-jin founds out Ryu's apartment and waits for his enemy to arrive back. After Ryu was knocked out unconscious by the booby trap, he brings Ryu to the riverbed where his daughter had drowned. Though he acknowledges that Ryu is a good man, he had no choice, so he drowns the kidnapper. Unfortunately, just as Dong-jin was burying Ryu's dismembered body parts at a desolate location, a group of men arrived to stab him fatally, with one of them placing a note on his chest to identify themselves as a terrorist group. It all turns out that they were the same people that Yeong-mi is talking about. The group then leaves Dong-jin dying beside his car. We've got a serious Downer Ending here.
Lee Woo-jin in Oldboy. Sure, he is the king of Disproportionate Retribution and a manipulative, sadistic, ruthless, evil man, but still, many viewers will say that his flashback to his sister's suicide is the most heartwrenching scene in the movie.
Brigadier-General Francis Xavier Hummel in The Rock. He's a leader of the rogue Marines who steals the VX gas-armed rockets from one of the military bunkers. Not to mention taking a big group of tourists hostage on the Alcatraz Island and planning to kill the San Francisco's population unless the government pay up the ransom. Before his said terrorism plan, there was his deceased wife. As it turns out, his main motive is to give compensation to the deceased soldiers' military widows and orphans. He also regrets when his men kills the Navy SEALs in the shootout. Also, Hummel puts Stanley Goodspeed and John Patrick Mason in one of the prison cells, telling them that the guidance chips are to be returned or he will kill a hostage. The next day, when he launches one of the VX rockets, he diverts its course from San Francisco into the sea, making it a bluff. Pity that Cpt. Darrow and Frye weren't about to agree with Hummel aborting the mission, and they are actually in just for the money. Hummel gets involved in the Mexican Standoff, which results in Mjr. Tom Baxter shooting Sgt. Crisp and getting killed. Hummel himself was fatally wounded after killing Crisp. He tells Goodspeed about the remaining VX rockets before dying.
Tia Russell from Uncle Buck. She's extremely harsh and critical to everyone around her, especially her titular uncle, but is also extremely depressed, bordering on clinical.
Raoul Silva from Skyfall. Sold out by M, tortured for five months, and tried to commit suicide via cyanide capsule only to end up horribly disfigured. His only goal now is destroy M and die with her.
GoldenEye implies this is true of Bond himself. For instance, the reason he sleeps around so much is actually that he's desperate for companionship due to the number of friends and allies he loses on his missions.
Harry from the first two Home Alone films and the hotel concierge from the second film. Harry is a hot-tempered burglar who 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 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.
In The Gamers 2: Dorkness Rising, Cass the Rules Lawyer clearly has some control issues. To make matters worse, he appears to have invited his ex Joanna to the gaming group in hopes of getting a second chance with her, only for her to hook up with Lodge, basically right in front of him.
General Zod from Man of Steel is a genocidal megalomaniac. But Micheal Shannon's performance, his character depth and his sorrowful tone of voice when his army is sent back to the Phantom Zone and his plans to create a new Krypton on Earth are ruined push him into this territory.
Gary and, to a lesser extent, Andy from The World's End. Gary's pretty selfish and only cares about completing the Golden Mile, but then you find out what his life has been like, and that the closest thing to a success he's had in his whole life was a failed attempt at a pub crawl. Andy is constantly serious, always talking down to people (especially Gary) and criticizing everything he does. But, when you find out why, you can understand why he's so cynical.
Red-Mist to alesser extent. He's much more sympathetic in the movie in comparison to the comic.
This will evidently continue in the sequel, as Red-Mist as Motherfucker's more violent acts are going to be removed, particularly the rape, to which Christopher Mintz-Plasse flat-out said "Thank God." He's still pretty evil in the sequel though as he murders Dave's father, kills Colonel Stars And Stripes, and attempts to rape Night Bitch (and when that fails, he puts her in the hospital).
Franklin Hardesty in the original The Texas Chainsaw Massacre. Considered one of the most annoying horror movie characters of all time, but consider: 1. It's obvious he didn't want to come on this trip in the first place. 2. He seems to be developmentally challenged, but is smart enough to realize the only reason his sister and her friends dragged him along in the first place is a feeling of obligation, and he resents being seen as such.