13 of the Unluckiest Pop Culture Characters

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It’s the most wonderful time of the year, when superstition meets a 1980’s film series about a madman in a hockey mask. If you’re reading this, you survived Friday the 13th yesterday — but for the uber paranoid, the lingering effects of the spooky occasion will hang over us like a black cloud all weekend. We’re celebrating the unluckiest time of the year with 13 of pop culture’s jinxed, ill-fated characters from film and television. Some of them deserved what they got, others are plain luckless, but we love (and love to hate) them all for one reason or another.

Jesse Pinkman in Breaking Bad

Everyone’s favorite high school slacker turned cry face champion on Breaking Bad has hit rock bottom and then some. When Jesse (Aaron Paul) isn’t dazed, confused, and frightened for his life, he’s manipulated by the only real father figure in his life — former chemistry teacher and meth partner, Walter White (Bryan Cranston). Jesse’s real family threw him to the curb, because they disapproved of his lifestyle. He’s been beat up by a crazed drug lord (Tuco) and DEA agent Hank Schrader (Dean Norris), held against his will, and coerced into killing. He’s also suffered the loss of his former girlfriend, Jane (Krysten Ritter) and remains haunted by the deaths of several children. We’re finally seeing Jesse take aim at Walter for all the wrongs during their tumultuous relationship, but the fate of his character still hangs in the balance. Will Jesse finally luck out for the finale of Breaking Bad?

Duckie in Pretty in Pink

Jon Cryer’s Duckie in Pretty in Pink suffers from eternal best friend syndrome with his pal, Andie (Molly Ringwald). Is there anyone who didn’t root for Duckie over “richie” Blane (Andrew McCarthy) in the John Hughes Cinderella story? Hearts melted everywhere when the Duckman told Andie he would have died for her. We’ve always pondered the might-have-beens of the Andie and Duckie relationship, imagining a life of synthpop bliss and a wedding at TRAX — with new wave Annie Potts officiating, of course.

The Griswold family (and Eric Idle’s unlucky passerby) in the Vacation series

Clark Griswold (Chevy Chase) wants to be the ultimate family man, but the dorky dad with vacation plans for miles is a total disaster. The misadventures of the Griswold family spread like a disease — especially where Eric Idle’s frequent “accidental” tourist character is concerned. The Griswolds have yet to enjoy time off without calamity and ruin, thanks to bogus bonus checks (Christmas Vacation), dizzying road trips to Big Ben (European Vacation), and dead aunt Edna (Vacation), but we only feel sorry for Dinky the dog. He didn’t deserve to go out like that.

Alma in Brokeback Mountain

A girl like Michelle Williams’ Alma Beers in Brokeback Mountain probably fantasized about her wedding day since she was a child, but sorry girl, you can’t compete with sweaty cowboy love in the great outdoors. Alma marries Heath Ledger’s Ennis Del Mar, who really has the hots for fellow sheepherder Jack Twist (Jake Gyllenhaal). Their connection goes beyond physical attraction, however, leaving Alma out in the cold.

Luke Skywalker in the Star Wars series

The next time you’re having a bad day, just remember that your father isn’t a Sith Lord whose reign of terror over an entire galaxy hangs over your head. Oh, and that whole being in love with your sister thing.

Toby Flenderson in The Office

Dunder Mifflin’s hapless human resources rep Toby Flenderson (Paul Lieberstein) is a sad sack. Unlucky and awkward in love (first with Pam and later with Nellie), Toby just can’t catch a break. His obsession with the Scranton Strangler consumes him, and when he finally decides to expand his horizons and move to Costa Rica, he’s severely injured upon arrival. The Office ends with the mournful and forgotten Toby never writing that novel or finding someone who loves him. Even his New York City roomies abandoned him. Sigh.

John McClane in the Die Hard series

How many times can terrorists attack a man before he’s considered a walking hazard?

Annie in Bridesmaids

A stunted 30-something takes on maid of honor duties for her BFF while her life crashes down around her. It sounds like the start of a dreaded Hollywood tale where the woman is defined solely by her love life, but luckily for the unlucky Annie, Bridesmaids offers something a little more than the usual rom-com. Annie may not have the social skills of her refined friend Lillian (Maya Rudolph), a job, or the boyfriend of her dreams (though some might say a jerky Jon Hamm is better than no Jon Hamm), but eventually Annie faces her future with determination. Hopefully things change for her for the better.

Theon Greyjoy in Game of Thrones

We were the unlucky ones after having to witness the extreme torture of poor Theon Greyjoy during last season’s Game of Thrones. Betrayed by his own crew, broken, and emasculated, Theon’s luck ran out a long time ago, but his sister may come to his rescue yet.

Principal Rooney in Ferris Bueller’s Day Off

Smart aleck high schooler Ferris Bueller proves to be elusive for principal Rooney, but that doesn’t stop the self-important dean from trying to catch the trouble-making teen in the act of skipping school. His efforts are fruitless, and Rooney is beaten and bitten while stalking Bueller at his home.

Everyone in Mad Men at one point or another

Where do we even start with the cast of Mad Men? The ad men and women of Sterling Cooper & Partners are beset with bad fortune. Between the secret affairs, unwanted pregnancies, failed accounts, suicides, and inescapable sexism and racism, the New York City agency seems cursed. Them’s the unlucky strikes, we guess. Let’s not forget, however, that although characters like Don Draper (Jon Hamm) didn’t have a fair start — the aloof exec watched his own father die and was raised in a bordello — he managed to secure a life of luxury for himself. It’s Don’s inability to connect with others and his own greed and selfishness that burdens him with bad fortune.

George Costanza in Seinfeld

A-class jerk and lazy schmuck George Costanza (Jason Alexander) deserved a lot of what he got on Seinfeld, but his relationship with Lady Luck wasn’t a good one regardless. The universe punishes the neurotic underachiever for constantly lying and scheming, resulting in bad relationships (never forget the shrinkage episode), struggles at his job, and crushed life dreams (hand model and architect just wasn’t in the cards).

Sam Merlotte in True Blood

Does Sam Merlotte exist just so the True Blood writers can inflict the crappiest stuff on him? Dead girlfriends, deadbeat brothers, rejection from the town fairy, and a deadly relationship with a maenad are just a few of the troubles Sam has faced. Whether he survives the next and final season of True Blood is anyone’s guess.