Barney Fife.
He just wanted to be the hero so badly and always ended up making a fool of himself. He was so clumsy with his gun that he had to keep the bullet in his shirt pocket–and if he EVER loaded the gun, he would shoot a hole in his holster, guaranteed. Then Thelma Lou, the woman he loved, married someone else–and he found out in the most humiliating way possible. To top that off, he tried to get drunk on the punch they were serving that night, and it wasn’t even spiked!
Ned Flaunders. He is a God-fearing good man, yet his wife dies, his girlfriend leaves him, his house burns down and his business almost goes under. And he lives next door to the Simpsons. His personality is so bad even his minister can’t stand him.
Anybody who took the name “Mrs. Cartwright” on Bonanza. Hoss, Adam and Little Joe are all borne of different mothers and if IRC each took a bride who died.
Nothing ever turns out right for Squidward Tentacles in SpongeBob SquarePants, or Moe the bartender in The Simpsons. Poor bastards.
True, but they gave him the wrong drink!
Tobias Beecher (Lee Tergensen) on Oz:
Tobias Beecher, an attorney, drives drunk and accidentally kills a little girl. Gets 15 years (maximum sentence), and with a felony conviction, is automatically disbarred.
Befriended by Vern Schillinger, Aryan leader, Tobias is made his “prag,” a swastika branded on his ass, and he is ass raped.
Beecher’s wife, mother of his two kids, files for divorce.
Schillinger, makes him lick his boots and eat pages from a law book, rips up his family pictures.
He gets hooked on heroin by Ryan O’Reilly.
Schillinger forces him to perform in a talent show in drag (makeup, etc.).
Schillinger dumps him, makes him wear a confederate T-shirt (hated by all non-Aryran brothers in the prison).
Ryan O’Reilly gives him bad PCP, he wigs out, throws a chair through a glass door, fragments fly into Schillinger’s eye. He’s thrown in the hole (solitary confinement).
After release, Beecher attacks Schillinger with a weight in the gym, ties him up, defecates on his face, and lands back in the hole.
Beecher is forced to perform oral sex on James Robson; he bites off the tip of his penis, lands in the hole – again.
Beecher gets a new cellmate, Chris Keller, who is actually working with Schillinger to undermine Beecher.
Keller gains Beecher’s trust (comforting him after nightmares of the car accident, etc.); they begin spending “quality time” together. He falls in love with Keller.
Beecher, clean and sober, is offered “moonshine” by Keller, a man he trusts and loves, to help ease his pain.
Keller ends up in the hole, so Tobias eases his depression with a jar of “moonshine,” and ends up becoming an alcoholic.
Keller gets out of the hole and devastates Beecher, by telling him he’s changed his mind – it’s over, he doesn’t want anything to do with Beecher.
Beecher goes to the gym, finding Keller and Schillinger together. Schillinger kisses Keller, Beecher flies into a rage. They team up to break both arms and both legs.
*This is just the first two seasons; there’s two more to go. *
Among other other things that happen, Beecher’s son is kidnapped (his hand is sent to Beecher as proof) then killed; his father, visiting him in prison is killed.
Also, Beecher eventually does get paroled, but because Keller, who has decided he loves him after all, sabotages him,* Beecher is back in prison within days.
Didn't he also get caught in the blast when a clinic where he was working got blown up beause they were performing abortions?
Yeah, little Tommy must have hated him.I’m only about half way through reading this thread, so this has probably been posted many times but…
He actually did catch the roadrunner once.
Bob McC
And he asked for no salt on his margarita.
There was salt, big grains of salt.
Two more-
Professor Fate played by Jack Lemon in the incredibly funny Great Race. He was blown up about four times, had his moustache frozen and broken off, lost the girl a number of times, attacked by Indians, crashed into by a train and hit in the face by a number of pies. And that’s only about a tenth of the problems.
Cactus Jack played by Kirk Douglas in The Villian which was a live action version of Willie Coyote and the Road Runner (if the road runner was a kind of fem Arnold Swartz…). Bolders rolled over him. He was shot, he shot himself, horses kicked him, he fell off cliffs, and fell into deep holes in rivers, to name only a few.
But hey, he did get the girl, didn’t he?
(That movie was freakin’ hilarious!)
I’ve always thought that if I had Ripley’s life from the Alien series, I’d have killed myself a long time ago. Of course, death didn’t help her much, her life still sucked.
Would it make you happier to remember that the film was based on the main character’s memoirs ?
Jacob Singer from Jacob’s Ladder.
Subject of secret Army mind control experiments.
Loses his mind slowly, finds out the Army has deleted his records, doesn’t recognise him as a combat veteran.
Tormented by demons who rape his wife.
FBI agents/demons throw him out of a moving car, he winds up in gutter where Santa Clause takes his wallet.
Those are the worst I remember.
But does it count if it was all a dream? 
I didn’t want to quote your whole post, but based on that intro, I’d say that everything else that happened to him (apart from the deaths of his son and father) were not “ridiculously bad fortune”, but well-deserved consequences.
Seriously, that should be the standard judicial response for drunk driving!