Mad Men star Jon Hamm isn’t really a sly skirt-chasing fox—he just plays one on TV so well that he won a Golden Globe and an Emmy nomination for it. Meet the man who embodies NYC’s louche lifestyle of yore.

It doesn’t take much to turn a man into a pompous, sex-crazed, chauvinist—just ask Jon Hamm, the star of AMC’s Mad Men. “It’s all in the wardrobe,” he says. “I put on the suit, slick back my hair, and suddenly I’m a megalomaniacal bastard.”

Jon doesn’t blame his character, Don Draper, for this behavior, though. He just considers Don—a hard-drinking, chain-smoking, woman-chasing advertising executive during that industry’s boom in 1960s Manhattan—a product of his time. “To be one of those guys in that city at that time was like being a kid in the greatest sandbox in the world,” he says. “You had a vibrant and vital social scene that was very attainable. It wasn’t just for the hedge fund guys, Eastern Europeans and the princesses. So you can’t blame these guys for doing whatever they wanted. That’s what they were being told to do: Take a bite out of the Big Apple.”

But once Jon, 37, steps out of his Mad Men costume of a dapper fedora, meticulously tailored suit and skinny tie, you’ll find a modest Midwesterner who feels more at home in jeans and a T-shirt. Even though this role has made his career and won him a Golden Globe, and more recently, an Emmy nomination, it actually pains him to say some of the sexist things he has to spout on the show.

“When Don says, ‘I’m not going to let a woman talk to me like that,’ those are really hard words to get out of my mouth,” Jon says. “I was raised by a single mom and am surrounded by strong women, so seeing females treated as nothing more than ornaments or toys doesn’t sit well with me. But it’s very true to life in the 1960s. The funny thing with men of that time is that even when they were being crass, there was a level of decorum. Like at a holiday party, when the men were literally chasing the secretaries around the office, after grabbing them, they would lead them back by the hand in a very chivalrous way. Now, [our society is] crass in a Girls Gone Wild, reality TV, tabloid journalism kind of a way—which is actually even sadder.”

It’s no shock that Jon was cast as Don. There’s something decidedly old-Hollywood about his charming manner, chiseled features and deep voice. (And though he no longer smokes, he does share the character’s love of good bourbon.) Those same characteristics are garnering him comparisons to another mature heartthrob, George Clooney, which nearly makes Jon blush. “The world still has a George Clooney. He’s alive and well and I think he’ll be here for a long time to come,” the actor says with a hardy laugh, showing he doesn’t take all of this newfound fame too seriously. “It’s obviously extremely flattering. So if someone out there thinks I’m capable of that, all the better.”

This kind of praise is still a new phenomenon for Jon, who was a struggling actor before Mad Men came along. He can soon be seen in the indie crime film The Boy in the Box and the sci-fi thriller The Day the Earth Stood Still (with Keanu Reeves and Jennifer Connelly), and “I owe it all to Mad Men,” he says humbly. “People weren’t clamoring to cast me before this show.”

After graduating from the University of Missouri-Columbia in 1993, Jon taught drama to eighth graders at John Burroughs School, his own St. Louis alma mater. In 1996, he packed up his 10-year-old beat-up Toyota Corolla and moved to Los Angeles with just $150 in his pocket, couch surfing at the homes of friends while he waited tables and tried to break into TV and movies. Once he had saved enough to pay his own rent, he moved into a place with four other guys.

“We lived near a Mexican super market where we could buy all the ingredients to make burritos for $3, so that was our go-to meal for weeks on end,” says Jon, who also became very familiar with Los Angeles’ public transportation system after his car was impounded.

A friend of a friend, actor Paul Rudd, introduced Jon to some key people in the industry. “It was the beginning of my career, and I’ll forever be grateful to him for that,” says Jon. “So cheers, Rudd.”

Even still, more than three years went by before Jon got a single TV or movie role. Then he met his now girlfriend, actress-writer Jennifer Westfeldt, at a party in Los Angeles while she was writing the movie Kissing Jessica Stein. She cast him in the film and soon after he landed a one-off guest spot as a fireman on the TV drama Providence that led to a 17-episode stint.

He was doing all right, but at this point it was Jennifer, 38, who was earning magazine stories and critics’ attention. “Part of being in a relationship is supporting your significant other,” says Jon. “Sure, I wished I was getting roles too, but I never felt jealous.” And maybe he’ll get a chance to repay a favor and help get Jennifer a role on his hit show soon. “There’s been talk,” he admits. “The creator, Matthew Weiner, thinks Jen’s talented, and she has a classic look that could work for the time period.”

Then the two would get to see more of each other. Right now they have to put in a major effort, with Jon taking off early from filming in Los Angeles to spend long weekends with her in Poughkeepsie, where she’s in rehearsals for the play Finks, about the blacklisting of actors during the McCarthy era.

The couple have been together for a decade, and share homes in Los Angeles’ Los Feliz neighborhood as well as the Upper West Side. “We just click,” Jon says with a smile. “We may not have a piece of paper that says we’re husband and wife, but after 10 years, Jennifer is more than just a girlfriend. What we have is much deeper and we both know that. To me, people [should] get married when they’re ready to have kids, which I’m not ruling out.” But right now, he says that their careers come first. “We both have a lot on our plates.” Plus Jon, just like his character Don, is currently enjoying his heyday: “I feel like the kid who finally got invited to the party, and I’m determined to stay up all night so the party doesn’t end.”

By Patty Adams