She has been through so much - The Corpse Bride.

The one who is constantly in trouble - Bender from The Breakfast Club, one of my favorite movies ever. And "Judd Nelson is fuckin' harsh".
 
Based on my collection -http://www.polyvore.com/were_all_pretty_bizarre_some/collection?id=2371884

Alvy: 'It's mental masturbation!"
Annie: "And you would know all about THAT, wouldn't you?"
Alvy: "Hey, don't knock masturbation! It's sex with someone I love."
 
There's sarcastic, and then there's Woody Allen.
 
The sarcastic - Annie Hall

I'm stepping through the door
And I'm floating in a most peculiar way
And the stars look very different today
Here am I sitting in a tin can far above the world
Planet Earth is blue and there's nothing I can do...
 
Space Oddity / David Bowie

"For me, stealing's always been a lot like sex. Two people who want the same thing: they get in a room, they talk about it. They start to plan. It's kind of like flirting. It's kind of like... foreplay, 'cause the more they talk about it, the wetter they get.The only difference is, I can fucksomeone I've just met. But to steal? I need to know someone like I know myself. "
 
The criminal - Lesbian icon Corky from The Wachowski Brothers' Bound.

My ipod's sixties playlist as a romantic movie shuffle.
Feel free to ignore.

The thief- the glorious Carmen San Diego.
 
Created in the Polyvore iPhone app. http://www.polyvore.com/iPhone

Couldn't think of anyone who would a better fit for "the stupid bad guy".
And yet, he's sort of boring, so I went for a meme based set. Also, it's kind of hard to keep up versatility after 41 sets.

As Ramona Flowers would say...
 
The tangled ex's: Envy, who used to date Scott, who's now with Ramona, who used to date Todd (Who once was a ve-gone, but now is begone).
 
Awesome movie.