Difficult Men: Behind the Scenes of a Creative Revolution: From the Sopranos and the Wire to Mad Men and Breaking Bad

by Brett Martin

  If Weiner had none of the New York street cred of Winter or Frank Renzulli (he would later joke, perhaps to Green’s further consternation, that he was the “first female writer on The Sopranos”), he connected with Chase and the show in other ways that were clearly a perfect fit.

  “Matt went to film school, David went to film school. They’d both watched all these movies I’d never heard of,” said Winter. “I used to sit there thinking, ‘God, between the two of you guys, you’ve read every fucking book ever written. I feel like an idiot.’” Weiner also brought a sense of nuance and a view of human interaction—how people rarely say what they really mean—that Chase immediately recognized as suiting the show perfectly. In “The Test Dream,” credited to both men, Tony, overwhelmed by complications involving Tony Blundetto, retreats to the Plaza Hotel. There, he falls into an extended dream sequence that was equal parts Freud, Fellini, and the Three Stooges, a fantasy of alternating power and performance anxiety that culminated in Tony’s high school coach taunting him for being “unprepared.” The twin codas seemed to sum up the range of both Chase’s and Weiner’s worldviews: at dawn, Tony calls a sleepy Carmela and tells her he’s had one of his “Coach Molinaro dreams,” perhaps the most tender moment the couple share in the entire series. Also, Tony decides he’s going to have to kill his own cousin.

  Weiner clearly treated his time on the show as a master class—not only in the art of television storytelling, but in how to be a showrunner. He left seemingly determined to emulate Chase, his mentor, for better and for worse.

  • • •

  Five years before, if HBO doesn’t call Matt Weiner back, Mad Men never sees the light of day. Period,” said one TV executive. Ironically, it was a company owned by Charles Dolan, the man who dreamed up HBO, that saved the universe of the Sterling Cooper ad agency from that fate. AMC had been, for most of its twenty-two-year existence, a commercial-free network showing older, cheaper-to-acquire movies. “It was like ‘the not-good Turner Classic Movies.’ We had black-and-white movies, but not the great ones,” said Rob Sorcher, the executive who would oversee the network’s transformation. Even more than FX, AMC was in a position to take a risk, to create an identity—Don Draper–like—out of almost nothing.

  “It started with Josh Sapan”—the chairman of what was then called Rainbow Networks—“coming into my office and saying, ‘Look, we need The Sopranos,’” Sorcher remembered. Sorcher had taken the job of senior vice president of programming, packaging, and production in the spring of 2002, just as AMC was undergoing its transformation from a commercial-free network to one that accepted advertising. He was an intense, mile-a-minute-talking veteran of the advertising business who had spent several years at the Cartoon Network, Fox Family, and USA. Since arriving at AMC, he had concentrated on programming that played directly off—and could be surrounded by—the network’s sole strength: a large library of movies. “We did documentaries about Hollywood, reality shows about making movies, some very interesting stuff, but that stuff didn’t pop, because nobody really cares,” he said.

  Now his boss was demanding that, starting from scratch, he produce an original, scripted series to rival the most important TV show in a generation. Sapan had good reason for the strategy: Cablevision, which owned AMC, was not a company on the scale of Viacom or Time Warner, which could use the leverage of many channels to force cable carriers to keep them on the air. “He was afraid that, in the digital age, a world of consolidation, the network was just going to drop into oblivion,” Sorcher said. “He wanted something of distinction. A signature show that viewers would care about, the press would care about, and that would give us some leverage going into talks with cable operators.”

  And Sapan also said the magic words: “He told me, ‘I don’t care about ratings.’”

  Nevertheless, Sorcher remained cautious, unsure of whether the company had the mettle and wherewithal to do what it said it wanted to do. He was reluctant even to hire a full-time staff member for what would be the network’s development department, reasoning that he didn’t want to lure somebody out of an existing job for one that might go nowhere. Instead, he made the unorthodox choice of hiring Christina Wayne as a “consultant.” Wayne had spent the past decade working as a screenwriter in New York and Los Angeles, writing and directing one independent feature, Tart, in 2001, and working as a writer-for-hire on many others. She had no TV or development experience and had barely heard of AMC. Still, in January 2005 she agreed to meet with Sorcher.

  “I spent the first fifty percent of the meeting just sitting there, pretending I knew what the hell he was talking about,” she remembered. “But then he got to the part about having $70 million to launch a scripted division and needing someone to go out there and find great projects. I thought, ‘Oh! That could be fun.’”

  Wayne set about doing just that. Sorcher’s strategy was to start with a miniseries, something contained—in both cost and commitment—that would serve to get the network’s feet wet. One of AMC’s perennial strengths had been westerns, so Wayne found a script for a two-hour movie called Daughters of Joy to which Robert Duvall and Walter Hill were attached. Stretched to a four-hour, two-part miniseries and renamed Broken Trail, it went into production. The process was rough. Hill and Duvall were at each other’s throats throughout. In postproduction, Duvall broke into the editing bay, took the raw footage, and made a cut of his own. But Broken Trail burst out as the highest-rated basic cable miniseries of the year. It was nominated for sixteen Emmys and won four.

  Cablevision, which had its corporate headquarters on Long Island and network offices across from Madison Square Garden, was hardly a glamorous Hollywood studio. The original-programming department—Sorcher, Wayne, Vlad Wolynetz, who would become head of production, and Jeremy Elice, brought in to open a West Coast office—were like peacocks in a chicken coop.

  “It looked like the office in The Office,” Wayne said. “Vlad used to say it was where mediocrity came to die.” Elice remembered the first time he and Wayne were to make a presentation to a meeting of the other Rainbow networks. Wayne met him backstage with a ten-gallon hat.

  “What is this?” he said.

  “This is our part,” said Wayne. “We’re playing prospectors for AMC: ‘We’re out there developin’!’”

  “It’s fair to say,” Sorcher summed up dryly, “that it was very unlikely that interesting programming would come from that environment.”

  With the success of Broken Trail under their belt, Sorcher and Wayne now went looking for a series. “I came up with this spiel. It was really just a wish list of what I wanted to watch on TV: ‘We want to do high-end, one-hour dramas. We want them to feel more cinematic and told the way a novel is told—slow-paced, slow burning, character driven.” The team had a rule, almost a mantra: “No doctors, no cops, no lawyers.” But looking at the shows that had done well for the network, they made a determination: a period piece would be okay.

  Ira Liss, a talent manager at Industry Entertainment, handed Wayne Mad Men. Despite David Chase’s recommendation, and to his puzzlement—“Here’s the guy who you’ve declared a ‘genius’”—himself—“telling you that a show is really good and you don’t even answer?”—HBO had ignored the script.

  “This has been passed on by everybody for eight years,” Liss told Wayne. “But I think you’ll like it.”

  Wayne, who had once tried to option the rights to Richard Yates’s Revolutionary Road, did. And Sorcher, who had started in advertising, did, too. Certainly the obstacles were clear: “Everyone smokes. They’re unlikable. It’s about advertising—there’s no international value in that. It’s slow. It’s period. It’s the worst idea ever,” Sorcher summed up. But in the particular economics of the moment, a big strikeout was better than a weak half swing. “I thought, if we put on these shows, and they’re low to middle quality, they’ll come and go and nobody’s going to care. But if I choose quality, some crazy insane
thing, and I know that ratings don’t matter, at least I’ve taken the shot. In a way, it’s a safer course than getting stuck in the middle,” he said. The goal was clear and defined. No basic cable show had ever won the Emmy for Outstanding Drama Series. “One hundred percent, this is the show that is going to win,” Sorcher told his staff. “It was built to win that award. That’s what it was designed for. If it doesn’t bring us that award, the system doesn’t work.”

  • • •

  If the Sopranos myth was of two notes (on the title and on “College”) and Six Feet Under’s was of one note (“Make it more fucked up”), then Weiner characteristically upped the ante by later claiming that he had received no notes on the Mad Men pilot. Still, as taken as she was with the script, Wayne did have a worry: “How do you get people to come back week after week to watch a show about advertising? That’s not going to be enough. There has to be what we called a ‘water cooler moment,’ where you go, ‘Oh, my fucking God. I have to watch next week!’”

  Weiner, then still working full-time in the Sopranos writers’ room, took two months to come back. When he did, it was with an entire twelve-episode arc, plotted out in breathtaking detail. At its heart was the backstory of Don Draper, prince of Madison Avenue but, like Jay Gatsby, a remarkable act of self-invention. He was, Weiner explained, born Dick Whitman, the illegitimate son of a prostitute, and had stolen a dead man’s identity in the Korean War. It was a story he’d been thinking about for years but never grafted onto the pilot. Still, he was willing to make only the smallest concessions to the script as written: one shot of a Purple Heart, hidden in Don’s desk, and the subtle sound of distant bombs when he stared into a light fixture. No extended flashbacks. No dramatic reveals.

  Apparently, it was enough. The AMC team went looking for a studio to partner with in making the pilot. For all the same reasons that had kept Mad Men unbought for eight years, nobody wanted any part of it. Finally, Sorcher decided to take a leap of faith; AMC would foot the $2 million bill for the pilot itself and hope to partner with a permanent studio later.

  • • •

  Of course, it was crucial to find the right actor to play Draper—that charming, enigmatic vault of secrets and shifting identities. “What I needed was an actor who could have one thing on the outside and something else on the inside,” Weiner said.

  The process followed a by now familiar trajectory. Jon Hamm, like Weiner, had been struggling in Hollywood long past his ingenue phase. A St. Louis native, he had watched ex-roommates like Paul Rudd get famous while he drew only the occasional guest role on cop shows. He was thirty-six, ridiculously good-looking, but well past the age of the kind of man-children then the vogue in Hollywood star making. It was, Hamm said, from the vantage of his later success, a blessing in disguise. He had seen the toll early stardom could take.

  “I see actors in this town who make it big young. They don’t understand the word no,” he said. “‘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.”

  And, it happened, Weiner was looking for something precisely like what Hamm offered: an unknown face, as James Gandolfini’s had been, and a full-grown adult—the kind that had once been common on TV and in the movies.

  “He reminded me of an old-fashioned leading man,” he said. “James Garner, Gregory Peck, William Holden. They’re handsome. They’re a little bit funny. They’ve got this wiseass-ness.” Not coincidentally, they were also precisely the kind of leading men who, in 1960, when Mad Men began, would soon be eclipsed by a new breed of counterculture heroes more on the order of Elliott Gould. How Don, his family, the ad firm of Sterling Cooper, and various other characters would survive the onrushing ruptures of the sixties was one of Mad Men’s most suspenseful ongoing mysteries.

  Matinee idol looks alone, though, wouldn’t have been enough for Hamm. As it turned out, his own history carried some emotional echoes of Don Draper’s world. He had grown up in St. Louis. His mother, Deborah, had moved there from a small town in Kansas at eighteen years old to find work as a secretary. She met and married an older widower, Dan Hamm, whose fortunes were going the way of his family’s business, hauling freight from the Mississippi to points around the country. Dan—nicknamed “the Whale” for his six-foot-three, three-hundred-pound frame and outsize personality—sold his business and looked for work in the New Economy. He peddled cars for a while. He dabbled in advertising.

  Hamm’s parents divorced when he was two, and he lived mostly with his mother. When he was ten, though, the two were on a trip to the St. Louis Art Museum and Deborah disappeared into the bathroom and didn’t come out for a long time. Hamm had to ask a stranger to go in and check on his mother, who had fallen ill. Not long afterward, he came home from school to find his father waiting with the news that she 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,” he said, “it was just pain management and deathwatch.”

  Hamm wound up living with his father and grandmother in a musty old house filled with stultifying sorrow. He spent most of his time at friends’ houses, cared for by a loose confederation of women he called “the Three Moms.” Then, when he was in high school, Dan too became ill, at one point losing 120 pounds from advanced diabetes. During Jon’s second semester at the University of Texas, Dan died and Jon dropped out. (He would eventually finish college at the University of Missouri.) Not much later, he lit out for Los Angeles.

  All of which is to say that Hamm, more than most good-looking, out-of-work actors biking to auditions down Santa Monica Boulevard, was in a position to know well the lessons of Don Draper: how quickly one’s world can be upended and how costly is the freedom to reinvent yourself and follow the American dream.

  By the time he was cast, Hamm said, he had read practically every scene in the pilot for auditions, beginning with one in which Don dresses down the oily, entitled salesman Pete Campbell, telling him that he’ll “die in that corner office.”

  “You could get a chimp to come in and read that scene and you will cast him,” Weiner said with characteristic modesty. “But the ‘It’s Toasted’ thing?”—a scene in which Draper comes up with the famous motto of Lucky Strike, while putting the audience in the strange position of rooting for a cigarette ad campaign—“Not everybody can do that.”

  More important, when Hamm left the room, Weiner turned to the casting director beside him. “That’s the guy,” he said. And: “That man was not raised by his parents.”

  • • •

  Predictably, AMC raised a concern. “They thought he wasn’t sexy and he had a shitty résumé and, in the end, they were getting cold feet about hiring an unknown,” Weiner said. Using frequent flier miles, Weiner flew Hamm to New York to meet with the network’s executives. The night before the audition, he met Hamm and some of the actor’s friends at a bar. “I told him: ‘You need to go in there with the confidence that I’ve told them I won’t do the show if you’re not in it,’” he remembered.

  It wasn’t strictly a bluff. Ten years into the Third Golden Age, the autocratic showrunner in chief was an institutionalized position. And as his model Weiner had Chase, who had given him instructions he would later use in two contentious contract negotiations: “You have to be prepared to walk away, and you gotta mean it. If you’re bluffing, if you’re not really there, don’t say it.”

  If now, before the pilot had even shot, Weiner had hardly achieved the stature or success that allowed Chase that attitude, he was committed to proceeding as though AMC needed him more than he needed them. “There was some talk about the network needing to oversee how Hamm was directed. I said, ‘No. You’re VIPs on set and I value your opinion, but I know what this thing is and that’s why I came here,’” he said. He told Chase about the conversation.

  “Well,” said Chase, “it better be good.�
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  With the cast in place, the pilot shot at Silvercup Studios over ten days while The Sopranos was on hiatus, borrowing heavily from that show’s crew and creative staff—including director of photography Phil Abraham and production designer Bob Shaw. With the final product in hand, Wayne and Sorcher once again toured the studios. This time, Lionsgate bit. Immediately after wrapping production on his final Sopranos episode—the next to last of the series, in which Bobby Bacala is killed and Silvio ends up in a coma—Weiner headed to L.A. to start writing.

  • • •

  When the Mad Men writers’ room convened, eight years of thwarted ambition was unleashed. Among those in the room were the husband-and-wife writing team of Andre and Maria Jacquemetton, whom Weiner had known since film school; an old colleague from The Naked Truth, Tom Palmer; a longtime sitcom veteran named Lisa Albert; and two young writers with little experience, Chris Provenzano and Bridget Bedard.

  For the first week, Weiner spoke almost nonstop. He had spent years imagining plotlines, reading reference materials, even collecting music that he wanted to use on the show. Now he downloaded reams of information while his writers scribbled furiously. At one point, he had written about 80 percent of a screenplay about Don Draper’s backstory, which he recounted in intricate detail. “He knew every side character, what towns they’d lived in, everything,” Bedard said.

  Every writer was tasked with bringing in a handful of random plot ideas—“An Episode About Brassieres,” “Pete Gets a Haircut”—which were written down on three-by-five index cards and pinned to a bulletin board, to be used in a pinch.

  Weiner paced nonstop, speaking in the voices of his characters, in particular the imperious office manager Joan Holloway. “It would just overcome him, as if he were in a trance,” said Provenzano. “Of course Joan is the bitchiest character. And Matt is a quintessential Queen Bitch. He could write that character for days and days.”