Buying the Glass Ceiling
Milo Roberts is, like, so totally over 1950s gender expectations. She's wealthy and she's powerful. She's also a woman. Predictably, this flummoxes most of the men she encounters. Take Jerry, for example. When he first sets eyes on Milo's posh hotel room, he immediately assumes that it isn't Milo's money that's paying for it:
JERRY: Hey, uh, how'd you come by all these worldly possessions? A rich husband or a rich father?
Jerry jumps to conclusions, and it turns out he's right. Still, that doesn't change the fact that Milo can buy and sell Jerry, or at least Jerry's artwork, even if he's not sure how much he should charge for it and has to ask Milo to take control and make him an offer. When Milo suggests that Jerry come back to her hotel room so she can pay him what she owes, her power over him is on full display:
MILO: Why don't you come to the hotel? I can pay you for them there.
JERRY: Fine. Is it far?
MILO: Would you care if it were?
Of course he wouldn't. If Milo's hotel were on Mars, Jerry would gladly jump in her spaceship, and Milo knows it. He's broke and dependent on the kindness and generosity of others. Milo, on the other hand, is independent. She may be bankrolled by her dad's suntan oil fortune, but she's burning her way through Paris, and making a name for herself, on her own.
Hangin' with Mr. Mulligan
Milo's self-possessed and sure of herself in a way that Lise, our other leading lady, isn't. She's not intimidated or befuddled by Jerry's aggressiveness, for example. When Jerry draws attention to her wardrobe, which is decidedly feminine and therefore freaks him out, Milo shows she can dish it as well as she takes it:
JERRY: That's, uh, quite a dress you almost have on.
JERRY: What holds it up?
In short, Milo's a woman who knows how to navigate a man's world. She's a power-player who can hang with the guys, but she's also fully aware that her status is threatening to most men. When Jerry suspects that Milo's interested in more than his art, he gets indignant and suggests that she hire an escort. Milo coolly tells him to, well, cool down:
MILO: I don't need a paid escort, and I'm not trying to rob you of your precious male initiative. I'm simply interested in your work and I want to get to know you better. Now is that such a crime?
Milo knows exactly how to handle that precious male initiative; she knows that, in her world, the male ego bruises easier than a month-old banana. That's why, when she suggests going out to dinner, she lets Jerry take her out to a place that he can afford. That's why she can deftly handle Jerry's tantrums, including the fuss he raises when she gives him a studio and lines up an exhibition for him. When Jerry ignores the incredible opportunity being handed to him and instead whines that his art takes time, Milo delicately calls him a slacker:
MILO: Look, you're a painter, and a good one. I happen to have a little drive. That's a good combination. Besides, you have to face the critics sometime.
The gal's got a politician's skills, and here's why: Milo's keenly aware that, in order for her to succeed at the game—whether that's success in the art world or success at winning Jerry's affections—she has to play by the rules. In An American in Paris, the first rule of Man Club is don't emasculate the man.
Man, I Feel Like a Woman
Milo has the power to shape Jerry's career, but she doesn't have the power to resist his charms, or reject them for what they are. Which is to say they aren't charms at all, but some thoroughly sleazy strokes of manipulation.
Jerry knows that Milo's into him, and he spends most of the movie shooting her down, whether it's telling her to hire an escort or flirting with Lise right in front of her. He doesn't see Milo as a woman, and he definitely doesn't see her as a complicated woman—you know, with wants and needs and feelings and all that stuff. Jerry only turns on the charisma with Milo when he wants something from her. When Lise breaks his heart, for example, he comes running to Milo and exploits her vulnerability:
JERRY: You and I are going out tonight. I'm going to take you to the art students' ball. You ever been to one?
JERRY: You'll love it. It's jet-propelled New Year's Eve, and everybody in Paris will be there.
MILO: It's costume, isn't it?
JERRY: Nevermind. I'll take care of all that. Leave it to me. Tonight's my night.
MILO: I feel like a woman for a change.
Jerry knows exactly what he's doing here. Milo's power comes at a price that's a nasty product of her time. She feels she has to sacrifice her femininity in order to succeed. So when Jerry offers to take care of everything, and seals it with a kiss, Milo finally feels like a woman; she doesn't have to tamp her femininity down to get things done.
We can't let Milo off the hook just yet, though. She may be powerful, savvy, and willing to sacrifice herself, but she's also a predator. Jerry may play her, but she plays him right back. Whether it's inviting him to a fake party or lavishing gifts upon him, her intentions with Jerry are never wholly on the level. Now, we know what you're thinking: "But Shmoop, that's what she had to do! The '50s were, like, totally messed up, and a guy just wouldn't be into a gal with that much money and power."
Fair point. The problem is, Milo doesn't even try to snag Jerry through honest means. She jumps right into buying his affection when she sees him selling his paintings on the street. Her game is all shame. Furthermore, as her exchange with Tommy at the jazz club shows, Milo's got a history of preying on young artists:
TOMMY: Milo, you're going to have trouble with that one.
MILO: No, I'm not. He's just not housebroken yet that's all.
TOMMY: When are you going to stop getting yourself involved with young itinerant artists? It never works. If they're no good, you're ashamed. And if they are, they get too independent.
MILO: Now just dance, Tommy, please.
TOMMY: Alright, but I'm warning you: he'll be out in four months, just like the composer and the sculptor.
Busted. Milo's an art cougar. While it's understandable to feel empathy for Milo as she tries to make her way through a man's world, it's hard to deny that she's in, well, a little bit of denial herself. She's a serial sponsor, and unless you're former president George W. Bush, you know how the old saying goes: Fool me once, shame on you; fool me twice, shame on me. In short, if Milo wants to be respected as the awesome, powerful woman that she is, she needs to start respecting herself first.