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07.15.2015by: Cherry Liquor

The Top Ten Hottest Trainwreck Characters of Film

I'm looking forward to watching TRAINWWRECK, if only because I've found myself in similar situations that Amy Schumer is shown getting into in the trailer for the film. (Always avoid the gym rat dudes, ladies. Not worth it, even if they look like John Cena.) I've also known my share of trainwreck women as well, something that Hollywood seems to be a bit obsessed with. Here are ten of my favorite hot mess, screwed up, unhinged trainwrecks in film.

#10 - Maggie Gyllenhaal (SECRETARY)

People talk a lot of shit regarding the purported unattractiveness of Maggie Gyllenhaal but I don't think I've ever heard someone claim that she isn't sexy. There's something amazing that happens when Maggie takes on a meaty role, especially in the first movie she did that really got her noticed, as a kooky young woman with a penchant for cutting herself to release the crazy within. SECRETARY is definitely not a movie for everyone but in a world where women everywhere are strangely embracing the imbecilically written FIFTY SHADES OF GREY as some kind of sexy blueprint, you'd think that more of them would have caught on to this film instead.

#9 - Thora Birch (GHOST WORLD)

If you grew up with a young ScarJo as your best buddy, you'd probably have some issues regarding your femininity in the world as well. Thora Birch falling out of favor with Hollywood is one of the silliest mistakes that Hollywood has made over the years. Yes, she's cute and she has a phenomenal rack but Birch was always one of the most on-point young actresses working. If you can watch her slightly demented, totally trainwreckish character Enid take Steve Buscemi to bed and buy into it, you get my point.

#8 - Anne Hathaway (RACHEL GETTING MARRIED)

Out of everything that Anne Hathaway has done over the years to prove that she's A Serious Actress, it's her role as little sister to the bride, Kym, who really does it for me. A recovering drug addict who will never fully gain the unconditional love of her family, Kym continually self-sabotages in that way that damaged people do. While we're supposed to be appalled by her haggard appearance, it's one of the more honest depictions of a beautiful woman fighting her inner demons, making Anne even more tragically beautiful.

#7 - Patricia Arquette (TRUE ROMANCE)

One might say that Tarantino likes his women a bit left of center. I'd argue that he simply recognizes that women are complex creatures who love, fight and screw up. Sure, that means they're trainwrecks but Q seems to understand that we love the messed up ones just a bit more. As Alabama, Arquette is a hooker with her training wheels still attached, making her susceptible to falling in love with one of her tricks. (Although, let's be honest, we all loved Slater pretty unabashedly back in the day.) She's goofy but tough, loving and vulnerable. A trainwreck, sure. But a damned lovable one.

#6 - Uma Thurman (PULP FICTION)

Mrs. Mia Wallace could have just sat back and led a perfectly pampered life, being married to a big time kingpin criminal who appeared to love her enough to tolerate her raging cocaine addiction. Mia, being the trainwreck that she is, couldn't just accept it. She needed to dance, yo! If you've ever had to have your heart restarted by means of a huge hypodermic needle through the chest, chances are good you're a total trainwreck.

#5 - Natalie Portman (BLACK SWAN)

I haven't been a huge fan of Portman for most of her more adult career. Some time around becoming a space queen, I lost interest. However, when it comes to some of the most screwed up women in cinematic history, Portman's unhinged ballerina gets top marks. The girl hallucinates so much (probably due to lack of nutrition) that the audience can't figure out what's real and what's imagined in her life. Hell, for all I know, she really did grow feathers during that final performance.

#4 - Juno Temple (DIRTY GIRL)

Temple has built her acting career from her tremendous ability to play some rather screwed up characters. Most dudes are going to say they like her psychologically stunted (and frequently nude) character from KILLER JOE but for me it was her turn as the white trash Danielle from DIRTY GIRL. She screws in cars outside of her high school and doesn't care. She balks at accepting her single mom's new beau and runs off with the awkward chubby gay kid from school. I love Danielle because by the light of most people's eyes she's a total screw-up trainwreck but ultimately she's a young woman far too liberated of mind for the rest of the world to know what to do with.

#3 - Kate Winslet (ETERNAL SUNSHINE OF THE SPOTLESS MIND)

I prefer to think of Clementine as being a free spirit who might benefit from the use of pharmaceutical assistance. She's wacky and at times a bit deranged, but wouldn't you be if your already fragile mind was tampered with? Not to mention the liberties all the men in her life take with trying to tie her down and claim her as if she was a possession.

#2 - Rose McGowan (PLANET TERROR)

When we first meet Cherry Darling (actually the origin of my nom de plume here), she's crying on stage as she performs her strip tease. The girl has a past and the past is making her crazy. Sure, she also ends up losing that leg but in keeping with her truest trainwreck nature, she applies lipstick by the reflection of a urine pan, heads out and eventually replaces her missing limb with a machine gun. Because that's normal... for a trainwreck.

#1 - Charlize Theron (YOUNG ADULT)

You'd think that a girl who grew up with a name like Mavis wouldn't have been the most popular chick in her high school, but that's what Theron's character comes back to many years after leaving her small town home. She's neurotic and a bit delusional. Between pulling her hair out strand by strand or spitting into a dry ink cartridge for one last print-out, Charlize is crazy and sad and still lovely through all of her mess. A trainwreck, indeed, but one you'd risk the damage for.

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