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

by Brett Martin

  “He’s wrong,” Chase said. “This is what these guys do. They send each other to jail by squealing all the time.”

  These would have been mere differences in opinion were it not for deeper suspicions Renzulli was beginning to have about Chase’s attitude toward the characters they were creating. In the case of the Paris blow job line, for instance: “They went for the fucking line, thinking it was funny,” he said. “It was clear that he found these guys amusing. And not in a good way.” The characters, he came to believe, were written with more contempt than empathy: “He would run away from any of those characters he wrote. He wouldn’t want to be around them for ten minutes.”

  To be sure, these feelings were colored by the writers’ far from amicable parting. Renzulli, eager to take advantage of The Sopranos’ success, had departed to take a development deal after season two. Before season four, he and Chase discussed his coming back to the show, but negotiations broke down over money. Renzulli insisted that he make more than what he had before leaving and, as important, more than his old protégé Winter. He was left with the feeling that Chase had gone behind his back to ensure that HBO didn’t give him what he needed. “I wanted him to come back,” Chase said. “When you’re doing a TV series, you want all the help you can get. And he was, on balance, a help.” But once Renzulli made his demand, he dropped his efforts to hire him back. “I stopped backing him,” he said.

  The deeper cut came when Winter and his girlfriend traveled to stay with the Chases in France. This, Renzulli felt, was an unpardonable betrayal, of the same kind he’d identified between Paulie and Christopher, Tony and Feech. The writer who may have most personally understood the codes and protocols that animated The Sopranos’ world left, devastated and embittered that they didn’t apply to the real world. The two barely spoke again.

  • • •

  It was not the only departure fraught with emotion. The second writer to join The Sopranos for its second season was twenty-six-year-old Todd Kessler, who shared an office with Winter. Kessler had grown up in Michigan and graduated from Harvard; like David Milch and Matthew Weiner, he was the son of a successful physician. In his short career, Kessler had shown a marked facility for connecting to older male mentors. As a theater and playwriting student in Cambridge, he had been taken under the wing of the playwright David Rabe. Later, Spike Lee offered him a full-time job at his production company and, when he turned that down, a chance to write a screenplay for a project Lee meant to direct. It fell through, but Kessler ended up as the youngest writer by far on the network TV show Providence, which debuted the same weekend as The Sopranos. The show featured a veterinarian character; NBC once gave him a perfectly serious note suggesting that each episode endeavor to feature a litter of puppies. When Chase offered him a chance to write an audition script, Kessler jumped.

  That script—“D-Girl,” revolving around Christopher’s foray into screenwriting—installed Kessler as the house wunderkind. Chase flattered him, asking for advice and reassurance. “He leads with his insecurity,” Kessler said. “I remember him asking, ‘I don’t know. Do we have a show here?’ I’m twenty-six years old, giving him a pep talk. It pulled me in. Bonded me with him.”

  Kessler threw himself into the show, staying on unpaid at the end of the season to watch the shooting of the finale, “Funhouse,” which he’d co-written. At the end of that season’s shooting, he said, Chase allowed him to come to Los Angeles to sit in on two months of editing, asking him not to mention it to the other writers. He became close with the Chase family, often going out to dinner with them. Kessler’s agent, who happened to also represent Chase, told him that Chase was considering the possibility of someday handing the show off to another writer and that he, Kessler, was being groomed.

  Chase dismissed that idea outright, saying he had never thought about handing the show over to anybody. In fact, he said, he had been growing increasingly unhappy with Kessler’s work as the writers reconvened for season three. “He had written a really good episode, and then it seemed to me that it was declining after that,” Chase said. “I don’t remember a lot of this, but I imagine he was being increasingly rewritten. Some people understand this completely strange, bizarre mind-set of organized crime. Some people don’t.”

  As Kessler remembered the sequence of events, on July 21, 2000, at about eight thirty a.m. the nominations for that year’s Emmys were announced. They included one for Chase and Kessler as the writers of “Funhouse.” Chase had written the first thirty pages—a long fever dream, occasioned by a bout of food poisoning and punctuated with graphic bathroom sound effects—in which Tony’s subconscious reveals what he’s known for a long time but refused to acknowledge: that his deputy, Big Pussy, is a rat. Kessler wrote the second half, in which Pussy paid with his life.

  Kessler spent the next ten minutes fielding congratulatory phone calls. Then came one from Chase’s assistant, saying that Chase wanted to see him in the office. When Kessler arrived, still buzzing from the news, Chase closed the door and sat down.

  “I guess the timing isn’t great,” he said, “but I think I need to end this relationship.”

  Kessler, astonished, asked what he meant. “I think you’ve lost the voice of the show,” Chase said.

  “David, the last thing we wrote was nominated for an Emmy, less than an hour ago,” Kessler said. “If you felt this way, why didn’t you say something?”

  Chase considered this. “I guess you’re right,” he said finally. “Do you want a second chance?” Kessler, more confused than ever, said yes. “Well, I need to think about it,” Chase said, showing him the door.

  Kessler left work and went to see his brother, Glenn, an actor and writer, at the SoHo apartment they shared. “As soon as I started to tell him what happened, I burst into tears. Like the embarrassing, childlike crying where you can’t catch your breath. The show had been my entire life.” As he sat on the curb, sobbing, a call came from Chase.

  “He was asking my advice on writing a scene. Like, would Tony say this or something else. No mention of what had just happened,” Kessler said. Two days later, Chase told him that he’d get his second chance, but that his next script had better come in “production ready,” with no need of revision. Given Chase’s way of working—and really any showrunner’s—this was as definitive a death sentence as a fish in the mail. Sure enough, several months later—and after the two had lost the Emmy to The West Wing—Kessler was summoned once again to Chase’s office. This time it was definitive.

  “I’ve never seen people get fired so fast. You walk into David’s office and ten seconds later the door opens and you have your shit in a box. He does not mince words,” Winter said. This time, he didn’t even see that much. Winter called Kessler a week later, wondering if he was sick, since he hadn’t been showing up for work. Chase hadn’t told anybody about the dismissal.

  Chase’s memory of the incident wasn’t nearly as dramatic. “It’s never good to be fired, maybe there’s no such thing as amicable, but it didn’t appear to me I was cold when I did it. Although, look at the message. It probably can’t come through very nicely.” About the unfortunate timing around the Emmy nomination, he said, “It’s hard for me to picture getting the news the nominations came out and then telling him, ‘By the way, you’re fired.’ I guess I’m capable of such thoughtlessness, but it’s hard for me to picture.” When told Kessler’s version, complete with its overtones of Freud and betrayal, he said dryly, “I might have had more on my mind than he did.”

  A few years later, Kessler wrote the pilot for a new series of his own, to appear on FX. Rather than assume an autocratic role, he would share the duties of showrunner with his brother, Glenn, and a writer named Daniel Zelman. The series wound up running for five seasons and winning four Emmys and sixteen additional nominations; along with Mad Men, it was one of the first two basic cable series to be nominated as Outstanding Drama Series. The plot revolved around a terri
ble boss—brilliant but manipulative, vain, imperious, unpredictable—and a young, talented, but impressionable employee who finds herself seduced, repelled, and ultimately both matured and corrupted by coming into her orbit. It was, he said, based in no small part on his experiences working on The Sopranos. The show was called Damages.

  • • •

  Chase’s announcement at the MoMA panel was only the first of several false stops for The Sopranos. Chase compared the show with Russia’s Mir space station, left up in orbit long past its originally intended expiration date. At the end of each season, spent and exhausted, he considered leaving it to drift off into space. “David always said that when we have an episode about Meadow getting her driver’s license, you know that we’ve jumped the shark,” said costume designer Juliet Polcsa.

  “You do all the easy ideas the first season, the first ones that come to you,” Chase said. “The second season you do the next best ideas. Each time it becomes harder and harder not to repeat yourself and to come up with something fresh that feels different.”

  Eventually, during each hiatus, ideas would start to flow, and Chase would come back to the writers’ room with a long strip of taped-together 8.5-by-10-inch pieces of paper, a miniature version of the whiteboard, on which each character’s fate was plotted. Still, the process of turning that outline into episodes could be grueling.

  “It became a running joke at the beginning of every year,” Winter said. “We would be trying to break stories and there’d be a certain amount of despair, David going, ‘Ah, it’s taking so long.’ I’d say, ‘David, it’s not taking any longer than it has any other year.’” Winter would pull out the calendar from the previous year and point out that the first outline had not been done until after another two weeks of meetings. “I’d say, ‘David, we are not gonna leave this room until you’re satisfied and it’s great. It’s okay. It will not go on the air until we think it really works.’”

  The closest Chase came to actually pulling the plug was in early 2003, shortly after season four had ended. Without warning, he summoned Winter, Burgess, Green, and his wife, Denise, to his office one Sunday. HBO was asking him to commit to two more seasons. Season four had ended with the devastating episode “Whitecaps,” in which Tony moves out of the Soprano house. It would go on to win Emmys for Gandolfini and Falco and Chase, Burgess, and Green. It would, Chase thought, be an honorable place to end. “He really didn’t know, creatively, if he was going to be able to do it,” Green said.

  Winter, in particular, argued strenuously that they should go on. Eventually, Chase agreed, though he decided to take an inordinately long break. The result, over a year later, was the best of the later Sopranos seasons. The pattern, as the seasons had gone on, had become to sustain the plot by introducing a new adversary for Tony—first the coldly menacing Richie Aprile and then volatile, psychopathic Ralphie Cifaretto, both men who posed a physical, existential threat to our protagonist. Season five also began with the introduction of a new thorn in the Soprano side, only this time it was more complicated. Tony Blundetto (played by Steve Buscemi, who also directed several Sopranos episodes) was Tony Soprano’s cousin, and he wreaked his havoc by messing with the Soprano gang’s New York partners. This pitted Tony’s loyalty and affection against his sense of business and the Mafia code—ultimately forcing him to kill Blundetto to preserve his own way of life.

  • • •

  I wanted out,” said Robin Green of that Sunday meeting in Chase’s office. “But I would never have said that. He wanted us to say yes.”

  By this time, the relationship between Chase and Green had long since begun to sour. The two had worked together, on and off, since Almost Grown. Now, with Renzulli long gone, she and Burgess were the only writers left from the original Sopranos staff. Long ago, she and Chase had bonded over stories about their mothers. Coming into season five, Green noticed that Chase had moved her chair around the writers’ room conference table. “It was so he didn’t have to look at me,” she said.

  As Chase told it, the problem began and ended with the pair’s writing output. “From the beginning, there was something about The Sopranos they didn’t get. They either could not, or didn’t want to, understand the through-the-looking-glass quality of the wiseguy mentality. I sat there in a room while Robin argued with Terry all afternoon about whether Tony would have to kill Tony Blundetto.” The result, he said, was that he ended up doing more rewriting. “And the strange thing was that, as time went on, I was having to rewrite them more. They had like a reverse learning curve.”

  Still, the relationship was obviously charged with long-standing emotions. “She became more and more truculent and obnoxious in the room,” Chase said. “What she was good at was asking, ‘Why? Why would that happen? Why?’”

  “David’s a guy who . . . you kind of hold your breath around him. There’s a physical feeling of discomfort,” Green said.

  Things only got worse in the first half of season six, when Green and Burgess worked on a script—about Tony, convalescing from his gunshot wound, trying to relocate to a better floor of the hospital—that ended up getting killed outright, the only time that had happened. Finally, Burgess came up from covering set one day to find Green in Chase’s office, getting fired. (“Nobody ever wants to fire Mitch,” Green said, patting her husband’s hand.)

  “He had a list of infractions, some of them going back twenty years,” she remembered. “He could cite the time when I drank too much at a party and interrupted a conversation he was having.”

  Chase agreed to give them one more chance to finish a draft of the script they were working on, but the writing was on the wall. Two weeks later, neither argued when Chase told them the arrangement was over. Burgess placed his pencil down on Chase’s desk. “Well, shit, David, if you don’t think the work is any good, then fuck it,” he said.

  The conflict didn’t end there. Chase was furious when a story in the WGA’s magazine, Written By, seemed to suggest that Burgess and Green had quit because they disapproved of the show’s direction, rather than been fired—even more so when their next series, a traditional CBS cop show called Blue Bloods, was initially marketed as being “from the executive producers of The Sopranos.” (The writers said that neither incident was under their control.)

  For Green, the hurt feelings lingered. “I think about it all the time,” she said. But not to the exclusion of remembering what it had meant to be in that particular room at that particular moment in television history.

  “I have every reason to say horrible things about David,” she said. “And yet, when I think back, I had more fun than I’ve ever had in my life writing for The Sopranos. What happened on that show, how it changed our lives, the excitement of it, the fun of the first season, where we didn’t know it was going to happen . . . it was the most fun I’ve ever had in my life.”

  Nine

  A Big Piece of Equipment

  In Chase, Ball, and Simon, the new TV revolution had found its Moses, its Mensch, and its Mencken. It remained only to find its Magus. Which is where the third David of the Third Golden Age came in.

  David Milch’s success—indeed, the very fact of his continued, albeit intermittent, employment—was, in some ways, the most unlikely story of the TV revolution, the extreme edge of what the moment’s confluence of creative and economic forces allowed to take place.

  By the time the revolution dawned, Milch had already had by far the most successful tenure in network TV of all the showrunners it would elevate. He had started his career at MTM, the modern cradle of quality television, and had been a critical figure at Hill Street Blues, that company’s signature show. From there, he’d gone on to co-create and run NYPD Blue, which ran for twelve seasons and provided a crucial link to the Third Golden Age. He’d won four Emmys and been nominated for eighteen more. On paper, there was nobody better positioned to usher in, and reap the benefits of, the ascension of TV as an art form.


  But on paper, the record could hardly do justice to what, with vast understatement, could be called the uniqueness of Milch’s modus operandi, or to the challenges it presented. In a world that valued predictability, he was, by design and by compulsion, wildly unpredictable. In a business in which time equals money, it was one resource with which he could be amazingly profligate. The unlikely result: In a society of men loath to put value on intellectual distinction, much less give other men credit for having it, he was all but automatically referred to as a “genius.”

  The Milch story was no less a piece of mythology for being largely true: Born in Buffalo in March 1945, five months before David Chase, he was the son of an eminent but volatile, hard-drinking, and horseplaying surgeon. He once described himself as a “Jewish country day-school boy.” In 1962, he left home for Yale and “never went back.” Hailed in New Haven as a charismatic prodigy, he was taken under the wing of the critic R. W. B. Lewis and Robert Penn Warren—referred to decades later, at every possible opportunity, as “Mr. Warren.” Post-graduation, Milch was tapped to assist his mentors, and Cleanth Brooks, on a landmark anthology of American literature.

  He also developed several obsessive-compulsive conditions. These included addictions to alcohol and heroin, though they were not as immediately crippling to his ambitions to become a novelist as were such habits as rewriting the same thirteen pages of prose over and over again, word for word in longhand, for a year. Television proved a salvation, though not one of which the mandarins of Yale approved. Mr. Warren, Milch said, “refused to have a television set in his home, as though it was some crouching beast.” Nevertheless, TV’s “coercions of circumstance,” as Milch called them—speed, deadlines, the constraints of genre, the necessity of collaboration—would prove to be precisely what he needed to emulate his mentor and become an author.