Jon Hamm: Man of the Year, 2008

The 1920s Mediterranean-style house that Jon Hamm shares with longtime girlfriend Jennifer Westfeldt does, in fact, sit on a hill—an honest-to-goodness, nonmetaphorical geologic elevation that looks out over the neighborhood of Los Feliz and east toward the expanses of lesser Los Angeles beyond. Still, on a sunny morning when Hamm has agreed to take me on a tour of the homes he has occupied since arriving in L.A., it’s hard not to see it through a haze of myth: the end point in a story that—not unlike Mad Men, the show that’s made Hamm famous—is part American Fairy Tale, part American Gothic.

So bring out the capitals: Call it the House on the Hill.

Leaning up against the front door is a cardboard FedEx box addressed to Westfeldt and containing a dress for the actress to wear, a few days later, at the Emmys, where Mad Men will win basic cable’s first-ever Best Drama award. “I’ve been trying on dresses all week,” Westfeldt apologizes, upon opening the door. Blond, slim, and flustered, she drags the box inside with one hand while holding off Cora, an energetic pit bull–shepherd mix, with the other. She cocks her head upstairs, mock-aggrieved. “Meanwhile, he just throws on a tux and looks great, you know?”

Well, actually, yes, we’d noticed. If you know one thing about Hamm, it’s likely that, as Mad Men’s Don Draper, he occupies a suit with the physical genius of Michael Phelps sliding into water.

Today, though, he descends the stairs wearing plaid shorts, a white linen shirt, and soccer sneakers. Hamm unsuited is kind of a frat guy, every inch the rabid sports fan and former high school football star. He says things like “Dude” and “Sweet” and “Dude, sweet!” On his head is a St. Louis Browns cap (facing frontward, thank the Lord). He looks like the kind of guy who is physically compelled to put on shorts the moment the temperature tops fifty-five degrees, a diagnosis he cheerfully confirms. Credit the totemic power of a suit, but he looks a full ten years younger than Don Draper, with about half the weight on his shoulders. How it is that the actor manages to make his ’60s adman so much more than just another perfect design element on Mad Men’s gorgeously curated set is not yet clear.

“This is going to be great,” he says of our planned itinerary, a looping route through a city that he’s embraced as perhaps only a midwesterner can. “One: You’re going to get to see a shitload of L.A.” He pauses, grins giddily. “Two: I have an awesome car.

The ride is a sleek, brand-new 2009 Audi S4—its exterior and interior going by the downright Draperific names Meteor Gray and Magma Red, respectively. Hamm bought the car only after getting the green light from his business manager. “He said, ‘I spend my days trying to restrain guys from buying Ferraris when they score a onetime guest shot on According to Jim. I think you’re going to be fine,’ ” Hamm says. It probably helped ease the man’s mind that Hamm had also just finished shooting his part as the heavy in the Keanu Reeves eco-sci-fi blockbuster The Day the Earth Stood Still. “It’s the first car I’ve ever had that wasn’t ‘responsible,’ ” he adds, accelerating onto the I-5. The freeway is uncharacteristically free of traffic. But then, it’s been that kind of year.

Our first stop: a modest, English-cottage-style bungalow in the neighborhood known as West Los Angeles. This is where Hamm’s aunt and uncle lived back in 1995, when Hamm arrived on Thanksgiving weekend. Everything he owned was in a beat-up ten-year-old Corolla. In the rearview mirror was St. Louis.

The Gateway City in the ’70s and ’80s was a declining urban center surrounded by white-flight suburbs. Hamm’s family’s fortunes seemed to mirror the place perfectly. His mother, Deborah, had moved to St. Louis from a small town in Kansas at 18 years old to find work as a secretary. She met and married an older widower who already had two daughters. Dan Hamm’s family business, Daniel Hamm Drayage Co., had once provided horses to drag goods from laden barges up the banks of the Missouri River, there to be distributed all across the country. By the time Dan took over, shipping advances had long since diminished St. Louis’s role as any kind of real gateway. He sold his once quintessentially American business and looked for work in the economy that replaced it: He peddled cars for a while. He dabbled in advertising.

When Hamm was 2, his parents divorced. He lived with his mother and saw his father on weekends, sometimes tagging along to joints like Al Baker’s Restaurant, where Dan—nicknamed the Whale for his six-foot-three, 300-pound frame and outsize personality—would conduct business while Jon played under the piano. At home, Deborah was devoted to giving her only son a well-rounded, active education.

It was, in fact, on a trip to the St. Louis Art Museum that she disappeared into the bathroom and didn’t come out for a long time. Hamm, then 10, had to ask a stranger to go in and check on his mother. Not long after, he came home from school to find his father waiting with the news that Deborah was in the hospital. Doctors had removed her cancer-stricken colon along with two feet of intestine, but it was obvious the malignancy had spread much further. “From then on, it was just pain management and deathwatch,” Hamm says.

Deborah had been a devout Catholic, but for the simplest and most intuitive reasons, her death marked the end of churchgoing for her son. Nobody offered the 10-year-old therapy. (“This was the Midwest, my friend. Not New York. I think they gave me a book: How to Deal with the Death of a Parent.”) He was moved into the house that Dan shared with his own mother. It was the musty, cluttered home of an old lady. His grandmother, Hamm says, in a tone that suggests understatement, “was not the nicest person.”

“We were three generations living under one roof, which is difficult in the best of circumstances,” he says. “She probably felt like I was this weird kid who’d come along and was taking her son’s attention away in the winter of her years. The blessing was that school started at 8 a.m. and ended at 5 p.m., so I could spend a lot of time outside of the house.”

I’d been struck by how often Hamm’s high school came up in interviews he’d done—far more often, that is, than you would expect from a 37-year-old man hanging out with movie stars. At his house, he takes me upstairs to a small office filled with yearbooks, plaques for senior-athlete achievement, prom pictures (let’s just say he cleans up a little better these days), and other adolescent ephemera. It’s clear that the John Burroughs School—the kind of progressive place where one could be both a middle linebacker and the lead in Godspell without being compelled to beat oneself up—was a salvation. “It was stimulating, safe, and filled with friends,” he says. Hamm became the kid who was always around other people’s houses—popping up at the dinner table, crashing in the basement: “I knew where all the spare keys were kept.” In particular, three of his pals’ mothers took it upon themselves to look out for him. Their names, because such women should be acknowledged, are Maryanne Simmons, Susie Wilson, and Carolyn Clarke.

“We all felt a sense of responsibility to help mother him,” says Simmons, whose son befriended Hamm in the seventh grade. She and the others remember Dan Hamm as supportive—a backslapping, quietly joking presence at football games and school plays—but diminished, grateful to the women Hamm calls his “three moms” but also a little sheepish about it. “You got the feeling that he had once been Dan with a capital D, but not anymore,” Simmons says.

In fact, the onetime Whale was suffering from advanced diabetes, at one point losing 120 pounds in a matter of months. “He was basically dying of a hard life,” Hamm says, eyes fixed on the middle distance. “He’d fallen in love with two women. The first died and left him with two daughters to raise. The second divorced him, and then she died, too, leaving him with another kid. It was a heapin’ helping of tragedy for any guy.”

Outwardly, Hamm appeared untouched by his own man-sized portion of sorrow. “My first impression of him was of total intimidation,” says Paul Rudd, who met Hamm through a mutual acquaintance in St. Louis. “He struck me as one of those unfair guys who are good-looking, really funny, and good at everything.” Rudd is one of many who say that despite decades of friendship, he’s never had a conversation with his friend about his mother’s death.

When high school ended, Hamm headed for the University of Texas, trading the possibility of a football career (he’d been recruited by Ivy League schools) for an academic scholarship. During his first semester, Hamm’s grandmother died. During his second, his father became more ill. On New Year’s Day 1991, Dan died. Hamm was 20.

“I thought, Well, that’s the end of that,” he says.

Hamm finished college at the University of Missouri and kicked around St. Louis a bit more, but nobody was surprised when he packed up the Corolla with every-thing he owned and headed west. And so, on a November day, Hamm pulled up to the house outside which we’re now idling in the Audi. His aunt and uncle were away for Thanksgiving, so Hamm—master of the spare key—let himself in. He spent the holiday sitting on the porch, calling friends, telling them, “Dude! It’s eighty degrees! On Thanksgiving!

*****

There is, in fact, one earlier house in Hamm’s L.A. story, omitted from our tour because the address is lost to history. This is the apartment fondly remembered as “The Shithole,” where Hamm came to visit Rudd and another roommate, Bo, while still living in St. Louis. They spent two weeks on the couch, playing Madden football, inventing baroque Nintendo golfer names (Hammer Lou, Whipticle “Whip” Fadada, Nacho Heyerdahl: “The MexiSwede”), and eating takeout chicken from El Pollo Loco. On rare trips out, they went head-to-head in arcane, dice-based drinking games. “He is seriously the most competitive person I’ve ever met,” Rudd says. He declines to name a game or sport in which he may have ever beaten his friend, for fear of retribution.

And so begins the Struggling Actor portion of the Hamm Tour. South down Sunset we go, into Silver Lake. We stop outside the rundown four-bedroom on Maltman Street where the actor lived with a rotating cast of roommates for years. Hamm lingers here fondly. The landlady, an ex–soap star, was kind enough to let him slide on the rent, and it was close to the crosstown buses on Western Avenue, so he could get to auditions those times he had no car. (Or even when he did, as one harrowing peek into the mind of a struggling actor reveals: “I was always terrified of parking garages, because they would say $1.50 per hour and I’d only have five bucks in my pocket. What if I ran late?”)

On we go. West along Santa Monica. Left, down to Wilshire. We dip into Beverly Hills. You know you’re a real Angeleno, Hamm says, when you perfect a route across town.

We swing by the headquarters of the William Morris Agency—a Death Star of a building, with its black, mirrored facade and interlocking WM logo that looks more like a sinister XXXX. This is where Hamm first found representation, the entire television department crowding into one tiny office to watch him audition. “They took me on because they saw a guy who could work,” Hamm says. “And then I didn’t. For three years.”

He means this literally. For three years, Hamm did not score a single acting job. Which is not to say that delayed success didn’t have its blessings. “If I were 21 and doing this, we’d be having a very different conversation,” he says. “I see actors in this town who make it big young. They don’t understand the word no: ‘What do you mean I can’t kill this elephant, drop it on a car, set it on fire, and then snort it?’ Well, you just can’t.” (No, I don’t know what parties Jon Hamm goes to; yes, I’d like to find out.)

Still, while nobody’s pretending it’s coal mining, auditioning without success is a singularly shitty way to attempt to make a living. As if on cue, Hamm recognizes a bearded man exiting his car on the sidewalk, across Beverly Boulevard. It’s an actor who recently shot a guest part on Mad Men. “I’ll bet you anything he’s on an audition,” Hamm says. “See? He’s juicing the meter. Listening to his lines on his iPod.” I can almost see him suppress a shudder before the light turns green.

*****

At this point, our tour begins to encompass the ten years Hamm and Westfeldt have been together, with a notable corresponding increase in real estate quality. There’s the pretty West Hollywood house with the Spanish gate where Westfeldt lived when the two hooked up. There’s the bungalow in Thai Town where Hamm spent one year, telling Westfeldt that he just needed to know what it was like to have his own place. (“She got it.”) Then their first place together: the huge second-floor apartment in Los Feliz with its view of the Griffith Observatory. Here, Hamm says, is where he first felt like an adult.

Meanwhile, the casting ice dam was show-ing signs of cracking. He scored a -nineteen-episode gig on the TV show Providence. That led to a host of roles on more programs with interchangeable titles taken from place names and bureaucratic departments: Point Pleasant, The Division, The Unit, and so on. He landed a role in Mel Gibson’s Vietnam-era ego vehicle We Were Soldiers, which consisted primarily of gazing at Gibson in rapt admiration.

By now, Hamm was a veteran. So he knew that pinning one’s hope on any one role is strictly a sucker’s move. The lead in Mad Men was an even longer shot than most; AMC had never produced an original scripted drama series. It wasn’t likely to take a chance by handing the lead to an unknown utility man. Nevertheless, somewhere in the midst of the seven-audition process, he found himself sitting in a New York bar with a friend and saying aloud, for the first time, “I really want this part.”

Luckily, there was someone on the other side wishing just as fervently. As a writer for The Sopranos, Mad Men creator Matthew Weiner knew a little bit about what the right unknown actor, like James Gandolfini, could do for a series. He was convinced that Hamm was perfect for Don Draper—the illegitimate child of Depression-era losers who, through preternatural ambition, intuition, and a freakish twist of fate, reinvents himself as a prince of Madison Avenue.

“He looked like an old-fashioned leading man, like William Holden or Gregory Peck,” Weiner says. “But he wasn’t just a football player in a suit. You could see that he was intelligent. He was vulnerable. He was an adult.”

When Hamm left the room after his first audition, Weiner turned to his casting director and said, with absolute confidence, “That man was not raised by his parents.”

*****

Every great television series reveals its entire story in its pilot. (Remember Tony and Dr. Melfi’s first session? “Lately I’m getting the feeling that I came in at the end. The best is over.”) In Mad Men, there was this exchange, between Draper and Rachel Menken, a prospective client. The subject is love:

Don: The reason you haven’t felt it is because it doesn’t exist. What you call “love” was invented by guys like me to sell nylons. You’re born alone and you die alone, and this world just drops a bunch of rules on top of you to make you forget those facts. But I never forget. I’m living like there’s no tomorrow, because there isn’t one.
Rachel: I don’t think I realized it until this moment, but it must be hard being a man, too.

Mad Men may superficially be about the perks of alpha-maledom, but it’s also about its costs—the toll of living in the state of mortal combat that is the trade-off for absolute power. And it’s about a generation caught between shifting tectonic plates of history. It’s no accident that in talking about his star, Weiner invokes such premodern icons as Holden and Peck. They are precisely the men who will find themselves out of work as the Elliott Goulds of the world rise to leading-man status.

“It will be interesting, if we keep going, to see how Don deals with that, where he falls in the balance of power,” Hamm says. “Because if Don is one thing, it’s adaptable. He knows how to read a room.”

He is also, in nearly every way—politically, socially, emotionally, professionally—on the wrong side. That the show actually makes you like, even envy, him is one of its more brilliant and perturbing strokes.

“Look, if you were a white man, Manhattan in the early ’60s was a sandbox. There was tons of pussy. There were great restaurants, great bars, great strip bars—all within a $5 cab ride,” Hamm says. “But in the end, that stuff is all soul-crushing—the way that Girls Gone Wild is soul-crushing. It’ll make you want to kill yourself.”

Hamm makes no secret of where this vein of desperation comes from. On a wall outside his office, he shows me a photo of a weathered man sitting in a dark-paneled room, wearing a tweed hat. Judging by the sideburns and the green stripe on his cardigan, the photo was taken in the late ’70s. He’s looking at the camera with an expression both bemused and filled with deep-seated regret. In one hand, held with instantly recognizable precision, is a burning cigarette. This is Dan Hamm in his declining years, but it could easily be Don Draper in his.

“I remember the first time I was in costume: I was sitting in my dressing room, running lines in the mirror, and I thought: Oh, my God! I look just like my father,” Hamm says. “He was just so fucking sad. Here’s this guy that looks like he’s got the whole package, but there’s nothing inside but sadness.”

But Dan Hamm is only one part of the story. If you’re looking for someone who understands that your world can be upended at any moment, who knows—like Draper or, for that matter, Jay Gatsby—how hard and perversely won is the freedom to pursue the American dream, to light out for the coast and reinvent yourself from whole cloth, for that, you might want to look not to the father but to the son

*****

Back at Hamm and Westfeldt’s home, we sit in the sun-drenched backyard, watching hummingbirds dart in and out of the trees. Cora dozes at Hamm’s feet. At first, he says, the couple’s decision not to get married was a pointed one. “We thought, Marriage is for squares,” he says. “Now it’s more that neither of us has particularly good models of what a marriage is supposed to be. It’s not something we grew up wanting.” (Being among the last of their friends to remain childless does put a crimp in the couple’s social life, but as Hamm points out, “If you want to have dinner after 6 p.m., there are always the gays!”)

“I believe that happiness is fleeting,” he says. But that’s not the same thing as saying it doesn’t exist. “Look, I know I hit the jackpot here. I found this role that sits well on me. I’ve managed to become successful without any taint of compromise. I get to share it with my girl. I get how lucky I am.”

Drying on the back of a porch chair is a wet suit he recently wore while participating in the swim leg of a charity triathlon in Malibu.

“You dive in the water and you think, Shit. It’s cold. It’s too far. I’ll never make it,” he remembers. “But then you take a deep breath. You get a little groove going. You concentrate on the next buoy, then the next one, then the next one. You start to enjoy the swim. And then, all of a sudden, it’s like, ‘Sweet. I’m here.’ ”

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