Image via Complex Original
Brad Pitt stars as a badass in Killing Them Softly, hitting theaters today. But the truth is, this boy from Oklahoma has been killing them softly for years. And by them, we don't mean bad guys, but ladies. Famous ladies, at that.
He popped up on the national radar as Geena Davis' cowboy boy-toy in Thelma & Louise, and every woman in the theater swooned at his yee-haw shirtless magnetism. This was (and still is) a very pretty man, and it's a mojo that works well for him. Brad has tended to date co-stars, which makes his romantic hit list look a lot like his filmography. It also means he tends to date women who are sex symbols themselves.
Here are the top 10 women he's killed, perhaps softly, with his song. Or something like that.
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Shalane McCall
When: 1987
Brad scored a five-episode run on Dallas, on which Shalane played the daughter of Jenny Wade (Priscilla Presley). He was her onscreen boyfriend, but did something happen offscreen? He was in his 20s, and she was 14-ish.
Smash Probability: They kissed on TV.
Juliette Lewis
When: 1990-1993
When Pitt started to get regular work, he was inarguably handsome, but his leading-man potential was unclear. Two of his best-received performances were as slimebag criminal boyfriends, in the TV movie Too Young to Die? (1990) and the theatrical release Kalifornia (1993). Both were made with wild-child Lewis—literally a child, as she was 16 when they started dating.
Brad ended up going down the path of stardom suggested by A River Runs Through It, but you have to wonder who he'd be if he had stayed with Lewis. Perhaps the Mickey Rourke of his generation? Alas! We'll never know.
Smash Probability: Due to the laws regarding age of consent in various states, we must respectfully decline to answer this one, your honor.
Sinitta
When: 1988-1989
Sin-who? Sinitta is an American-born singer who had a string of hits in the UK in the '80s and was an early protegé of Simon Cowell. She was also his on-again, off-again girlfriend for about 20 years, starting in 1984.
Smash Probability: Established British pop star dates American quasi-nobody—you be the judge.
Jill Schoelen
When: 1989
Schoelen co-starred with Pitt in Cutting Class, a slasher horror flick that will forever be remembered only for being Pitt's first starring role. Schoelen will be remembered for (if anything) being Pitt's first rumored fiancé.
Smash Probability: We bet they were engaged in something.
Thandie Newton
When: 1994
It's a move that might someday be known as "The Brad Pitt": Make a movie, come away with a girlfriend. The movie (this time around) was Interview with the Vampire (1994) and the girl was a (then) little-known actress who played Yvette, a tasty girl on his plantation.
Smash Probability: Something about playing a vampire makes you score with your comely co-stars (we're talking about you, Robert Pattinson and Stephen Moyer).
Christina Applegate
When: 1989
Brad Pitt was still finding a foothold in Hollywood and fumbling around with famous babes in 1989, when he briefly dated Applegate. She, of course, was a mega-star, having endeared herself to high school boys everywhere playing TV's favorite sexy daughter, Kelly Bundy on Married With Children. When the pair showed up at the 1989 MTV Movie Awards, viewers had to be told the identity of this studly young fellow. Many years later, Applegate expressed regret at having left the awards show with someone else.
Smash Probability: Applegate said the relationship evolved from "just friends" to something more, and then quickly ended. Is it possible they didn't do it? No, that's not possible.
Gwyneth Paltrow
When: 1994-1997
Brad and Gwyneth were Hollywood's most beautiful couple. Hell, if there is one thing this list proves, it's that Brad + woman = Hollywood's most beautiful couple. But their sustained relationship and engagement made them extra-beautiful, and the mix-and-match hairdos were the icing on this cake of celebrity cuteness. So, of course it couldn't last.
Smash Probability: Are we to assume these two had premarital sex? Like, naked and everything? Gosh, it really is Sodom and Gomorrah out there in Hollywood.
Robin Givens
When: 1988-89
What kind of fool dates Mike Tyson's ex-wife? This kind of fool. And there was, apparently, some, ah, overlap in their relationships with Givens. Mike Tyson recently recalled an incident in his one-man-show: "During our divorce, we were f*cking. And one day, I’m going to her house to bone her again and no one’s home, and I’m leaving and she’s pulling up with Brad Pitt, and I’m sad because I’m not going to get any more p**sy," he told Global Grind. "He wasn’t Brad Pitt back then. He was just some little beach-bum-looking dude. 'Hey dude' kind of guy. He was probably selling his body for money or something, I don’t know. He was very pretty."
Smash Probability: Beyond a doubt. Why he didn't get his pretty face smashed in by Tyson is the mystery here.
Jennifer Aniston
When: 1998-2005
The prettiest boy in the world falls for an attractive sitcom star. After the fizzling of Paltrow-Pitt, surely Aniston-Pitt would last. And it did (kind of); the couple was married in 2000 and stayed that way for nearly five years. Then Hurricane Angelina busted Brad's levees on the set of Mr. & Mrs. Smith, and Jen's fairy-tale future was done for.
Smash Probability: The rumor was that the couple split largely because Jen didn't want to make babies with Brad. Though we imagine they went through the motions quite a lot.
Angelina Jolie
When: 2005-present
The consensus sexiest woman in Hollywood at the time, Angelina had been divorced twice and had a bit of a cuckoo sex appeal; she and then-husband Billy Bob Thornton wore vials of each others' blood around their necks. Brad and Angelina fell for each other on the set of Mr. & Mrs. Smith, which was a problem as he was still married to Jennifer Aniston. That situation was put out of its misery and a year later Angelina announced she was pregnant with Pitt's child. Brangelina is/are currently engaged.
Smash Probability: Oh yeah. If Brad Pitt and Angelina Jolie aren't having sex, and a lot of it, what hope is there for the rest of us?