After film school at USC, Weiner was supported by his wife, Linda Brettler, a successful architect, and wrote script after unsellable script. He was a writer on sitcoms like Party Girl and Becker, but got tired of pitching jokes. "I let my contract run out on Becker," he says. "I decided I would rather change my career than go back there." After winning $8,500 on Jeopardy!, he used some of the money to make an unreleased autobiographical film called What Do You Do All Day? It was about an unsuccessful writer supported by his architect wife. "It's loosely based on The Odyssey," Weiner says sheepishly.
But he couldn't let go of a pilot he started writing in 1999: Mad Men. He had no special interest in the early Sixties, no connection to the world of advertising. Yet somehow, this project became his obsession – an epic pilot, the only one he ever wrote. "I wanted to write the greatest pilot ever," he admits. "That was my ambition. I wanted it to be profound, and 1 wanted it to be true, and I wanted it to be about a man my age and what I was interested in: Who do you look up to? Why am I still 18 inside? Why am I so ungrateful for everything that I have? And who am I?"
He felt unworthy of his giant ambition. "I hadn't written anything else, and I never sold anything," he says. But it got him his big break. In 2003, on the strength of the Mad Men pilot, David Chase hired him to write for The Sopranos. Two weeks after he started, he was told to stay home from work one day. People felt he was talking too much in story meetings. "It was really embarrassing," he says. "You're on the Yankees, and you're swinging at every pitch."
Chase recalls that Weiner, with whom he eventually became good friends, never really shut up. "There was a lot of talk and chatter in the first few weeks – so much that I couldn't think," Chase says. "Later on, as he became part of the fabric of the show, even though he would get 'no' 10 times in a row, he would still come at me. Whether or not his ideas were used, Matt understood the characters and was somebody I could talk story with. Obviously, now his ideas are used all the time. He needed his own show for that."
When HBO passed on Mad Men, Weiner took the pilot elsewhere, and he has spoken of his disappointment over the rejection. If it seems personal for him, that's because it is. In his head, the characters on the show are all reflections of himself. Not just Don Draper – every single part.
"There's no doppelganger there," he says. "I am a mixture of Roger, Peggy, Don, Pete, Joan, Betty. They all behave in ways I'm embarrassed to behave, and they all have qualities I wish I had. There's a lot of Joan in me: She has sexual confidence, which I wish I had. Pete is the guy I tried to be in high school: I was the towel snapee. I'm attuned to moments of humiliation. When Peggy is dancing in one episode and Pete says, 'I don't like you like this,' it was a hard thing for me to admit that I had been him – jealous and cruel. If you're a mean or vindictive person, I don't think you can learn it. You have to be raised with it."
Was Weiner raised with it? "I was raised with all of it." Both parents? "It's a mother thing, and it's a father thing. We're all like that to each other. Everyone's family is like this. That's what this thing is about. Mad Men is a constructed world for me to talk about how I feel about the world, for me to talk about my family, talk about my parents, talk about my fantasies, see my wish fulfillments, trash my enemies, vanquish my fears. Just to see them played out."
From a certain angle, you can see the entire history of American television encapsulated in Mad Men. Here's a brilliant writer not allowed to watch TV growing up, who then proceeds to devote his adult life to creating a lavish vision of all the tawdry TV fantasies he wasn't supposed to have watched. For his leading man, he creates a goyish Midwestern hero whose life is based on a lie. But through that deception – that very American act of self-creation – Don Draper discovers an authenticity he probably would never have found if he had remained Dick Whitman, the son of a violent hick and a prostitute who died in childbirth. Draper's success, as envisioned by Weiner, turns on his ability to make other people envy him, his power to make people want to either stand in his shoes or get into his pants. And for all his own success, Weiner admits he's still driven by such petty impulses.
"Life's not fair," Weiner says. "You get to a certain point where you're too old to be saying that, but it never stops being infuriating." No matter how much you rise to the level of a Don Draper, you never outgrow the temptation to escape into some-body else's identity. "I worked with a guy who said he went to Harvard," Weiner says. "Then everybody found out he didn't go to Harvard. We still saw him every day, and nobody gave a shit. It was shocking to me. I was like, 'Oh, my God, I could have told people I went to Harvard all this time?'"
Weiner was picturing leading men from the Sixties when he created Don Draper. "James Garner played this kind of corrupt Boy Scout in a number of movies," he says. "I saw black hair. I saw – if Gregory Peck and James Garner had had a baby, that guy."
The guy he got, Hamm, had been in Hollywood for a decade, with a list of credits split among forgettable TV shows (The Division, Providence), small-budget movies (Kissing Jessica Stein) and waiting tables at restaurants (at least one of which, Cafe Med, on Sunset Boulevard, wasn't bad). The year before he auditioned for Mad Men, he read for seven TV shows and completely struck out. "Seven tests, zero jobs," he says. "I was supernervous, nonpresent and terrified."
Hamm auditioned for Mad Men six times, but Weiner knew immediately that the actor had something in common with Draper. "That man was not raised by his parents," he famously told his casting director the moment Hamm left the first audition. The hunch was spot on: Hamm's parents split up when he was two, and he was raised mostly by his grandmother. How could Weiner tell? "Without sounding too California, there's a kind of AM radio that goes on when we're casting that gives you an intuition about a human being," he says. "I got the feeling that Jon understood a kind of independence, and he had a wound."
This evening, drinking a gin and tonic at a rooftop bar high above Sunset Boulevard, Hamm comes across more like a hand some cop than a leading man: dark jeans, black sneakers, navy-blue windbreaker, aviator shades. He looks five years younger than Don Draper and moves with the easygoing, athletic boyishness of the high school jock he once was. "I play a character that's constantly dressed up," he says with a shrug. "I don't really have much in comparison to the way Don holds himself. I'm not that guy. I don't really look like that."
So do clothes make Don Draper? "Part of it is the suit, but another part is a choice," he says. "This is a person who takes himself very seriously at work, a guy who's going to walk in and command a room. I'm not that way in real life. I don't grab the mic." Still, he instantly identified with Draper's cutthroat nature. "My life at the time was trying to get a job," he says. "Talk about ruthless – being an actor in L.A. and not working is nothing but hustling. I just really responded to it on some visceral level, and that may have been what Matt picked up on. That may be why the character resonates coming from me."
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