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

by Brett Martin

  In this struggle, Milch himself was not unlike the citizens of his Deadwood or, for that matter, any of the difficult men who populated TV’s Third Golden Age, from Tony Soprano on. All of them strove, awkwardly at times, for connection, occasionally finding it in glimpses and fragments, but as often getting blocked by their own vanities, their fears, and their accumulated past crimes.

  “We’re in a stream or river or something,” Milch said. “We are being carried along on something, in which technology has taken over from religiosity. And the story which is being told is the story of the individual trying to learn how to fucking swim.”

  Ten

  Have a Take. Try Not to Suck

  In December 2003, five white men in various stages of middle age gathered at a hotel in Tarrytown, New York. By day, they played competitive racquetball games. Somebody with a little foresight, and a concern for productivity, had chosen a hotel that didn’t have a functioning bar. Instead, at night they shot pool for money until an employee kicked them out of the rec room for gambling. In between, meeting in the living area of a hotel suite, they decided to elect a white mayor in an overwhelmingly black city, reform a major police department, and, just as a policy experiment, legalize drugs.

  The Wire was on hiatus between its second and third seasons, and the men in Tarrytown were the show’s brain trust: David Simon, Ed Burns, Bob Colesberry, and George Pelecanos. Also there was William Zorzi, one of Simon’s old colleagues from the Sun. Zorzi was working on a book project that he and Simon hoped to get off the ground in nearby Yonkers, so Simon invited him to sit in on what Colesberry had arranged as a kind of brainstorming retreat for season three. Simon had an ulterior motive, too: Zorzi had been a political reporter, and despite the pronounced grumbling of his main collaborators, Simon planned to use season three to take on City Hall.

  Viewers of The Wire, what relatively few there were at that point, had already learned that they might be expected to follow the show in unexpected directions. Season one had been a beautifully self-contained tragic drama. Like season one of The Sopranos, it had also ended in something of a narrative dead end. The eponymous wire was dead; the investigative detail had been broken up, with McNulty banished to the marine division; Avon Barksdale had reclaimed his hold on the Western District’s drug trade; and, generally, the powers that be on both sides had groaned, possibly swayed a bit, but then settled back into place, as implacable and unyielding as ever.

  Even given that narrative challenge, though, season two came as a shock, relocating a major part of the action to Baltimore’s dying waterfront and introducing an entirely new cast of characters. Cynics suggested that the shift to a subplot that included mostly white characters was a pandering response to the show’s poor ratings. Nothing about Simon’s personality made that seem likely, though. And if the goal was giving HBO’s viewership faces to which it could relate, a roster of roughneck stevedores, truck drivers, and union leaders would have to be seen as a questionable strategy, at best.

  In fact, Simon’s fallback plan, if The Wire didn’t get off the ground, had always been to continue the series of year-in-the-life, nonfiction books he’d begun with Homicide and The Corner. He had even discussed the next installment with his editor, John Sterling, who envisioned the series in the grandest terms. Simon, he said, was turning Baltimore into his own version of William Faulkner’s Yoknapatawpha County. The proposed third book would follow four longshoremen as they dealt with an industry that was disappearing, if not already vanished, in cities up and down the eastern seaboard. As Simon put it, about season two, the story was about “the death of work.”

  Not everybody was happy about The Wire shifting to tackle that topic. “It just didn’t feel like The Wire,” said Burns. But Simon was vehement: by turning their attention to a different sphere early, he argued, they would be claiming the prerogative to do anything they wanted later. “We claimed the whole city,” he said. “If the show survived, we could go anywhere. And if it didn’t survive, if it was only going to survive as a cops vs. gangsters thing, then fuck it, I didn’t want to do it. There wasn’t enough there to waste five years of my life on. It had to grow. So, let’s take our shot now.” The result would be like a brass rubbing, each season uncovering a new section of the landscape, until by the end, an entire panoramic metropolis was revealed.

  If, in light of that goal, the title The Wire seemed oddly literal and unambitious, Simon disagreed. “In my mind it was never just about the wiretap. It was about the delicate high-wire act, about the connections between people. It worked on that level. We’re all connected in some way.”

  Some critics regarded season two of The Wire as the weakest of the first four seasons, the one in which romanticism most clouded Simon’s usually clear-eyed judgment. Certainly it was a premonition of the far more serious problems to come in season five. But it was also the season that revealed, thrillingly, the scope of what The Wire project would be.

  At the end of the season, The Wire won its one relatively easy renewal from HBO. Simon even began thinking of a spin-off focused on politics and tentatively titled The Hall. When that failed to get off the ground, he decided that The Wire could accommodate an area of the brass rubbing even farther afield from its original focus. The story he brought to the table was based closely on the career of Martin O’Malley, the young white Baltimore city councilor who improbably split the black vote in 1999 to be elected mayor and later became governor of Maryland. “The journey of the serious journalist is ‘Why?’” he explained. “Who, what, when, where, how—a fourteen-year-old with a phone and a formula can write those stories. Why did something happen is epic. So if we’re trying to explain why the American empire is in decline, why we can no longer solve our problems, or even address them, then we have to introduce the political realm. And so what if it was an editorial?”

  Once again, he faced resistance from his fellow writers. All of them.

  “I thought it would be boring. We’re barely holding on by a thread [ratingswise] anyway. Let’s not do something where the audience is going to take a piss break every time the mayor shows up,” said Pelecanos. “The discussion went on all season. I’d argue against those scenes, and David would say, ‘You just don’t want to write them.’ Yeah, because they’re fucking boring, David. Give me a scene with Bunk and McNulty in a bar talking about their dicks. That’s what I want to write.”

  The battle was a matter not just of taste, but of real, quantifiable space. Even given the expansive scope of serialized TV, screen time is a zero-sum game and every minute given to a new character or plot arc means one fewer for everything else. Viewers of a show deep into a long run often look back on early seasons with something like the nostalgia of a firstborn child: “Remember when it was just us?”

  “If you look at season one or two of The Wire, you’ll find an A story line, and a B story line, with maybe a small C. All of a sudden, we started having A-line, A-line, A-line, B-line, B-line, C-line, C-line . . . and it’s like, ‘What the fuck are we doing here?’” said Burns.

  This was the flip side of Simon’s determination to expand The Wire each season. You can see it in Pelecanos’s story notes and beat sheets, handwritten on legal pads, which begin season three in neat, amply spaced penmanship and grow increasingly more cramped and chaotic—filled with arrows, cross-outs, reorderings, and parentheticals—as the episodes progress. The notes are also tantalizing glimpses into phantom story lines left on the cutting room floor: at various points, the plot included Omar kidnapping Poot, the hapless Everyman corner boy, and, as disturbing, Herc wooing Beadie Russell.

  The squeeze wasn’t felt just by writers. A character with less screen time can’t complain, but that character’s corresponding actor may need some significant ego massaging. In season two, Seth Gilliam and Domenick Lombardozzi found themselves in a position almost precisely parallel to that of their characters, Carver and Herc: relegated to the sidelines of th
e action—which meant shooting mostly second unit with Bob Colesberry—and increasingly frustrated. “We would bitch and moan and complain. It got to the point where we were calling our agents, ‘Get us off this fucking show,’” Gilliam said. “I told Dom, ‘I feel like George Steinbrenner signed me because I used to be a guy who beat the Yankees. And now I’m sitting on his bench just so I don’t beat them.’”

  Eventually, a meeting was set up with Simon. “We told him, ‘We’re very frustrated.’ He’s like, ‘That’s great. Frustration is good.’ We say, ‘Yeah, but we’re really frustrated.’ He’s like, ‘Your characters are frustrated. You have to use that. But trust me, in season three you guys are gonna have a lot more to do. Season three is gonna be great. I’m still developing it, but all I know is Herc and Carver are gonna have a lot more stuff to do. And for right now, frustration is good.’”

  Burns was never entirely convinced that the real estate spent on the political story line was worth it. “You could have played it a lot of ways without going all the way up to the mayor. It takes up an awful lot of room. And we’d tend to get stuck on whether O’Malley did something or not.”

  Pelecanos, though, was a convert. “The kicker was, once I saw what we did, the political thread kind of made the show whole, took it to another level,” he said. “Up until that point, you didn’t understand how things connected, why there was a breakdown in the system. To me, that’s what made it. David was right all along.”

  • • •

  There were two other major arcs to be plotted out that season. Years before, while doing their reporting for The Corner, Burns and Simon had found themselves one evening on West Baltimore’s Vine Street. “The sun was coming down, there was this redness in the sky. And somebody must have had some good shit out there because everybody on the street was fucked up except David and me,” Burns remembered. “And David says, ‘You know, if we could put ’em all here, it’d be great. This is what they ought to do. Put them all in one place, so the cops can do their job and the neighborhood can breathe freer.’”

  The result was a fascinating, if credulity-stretching, thought experiment: What would happen if drugs were legal? This plot, too, required the introduction of a new character: veteran police captain Bunny Colvin, who had made a brief appearance in season two. Fed up with the endless cycle of petty drug violence in his district, Colvin decides single-handedly to establish a free-trade zone—“Hamsterdam”—in which dealers may operate with impunity as long as they don’t impose on the rest of the neighborhood.

  “‘We’re all good liberals here,’ we thought. ‘Let’s put our money where our mouths are. Really see what would happen,’” said Pelecanos. “We didn’t want to push an agenda that said this was going to solve all the city’s problems.” Far from it, in fact. In constructing Hamsterdam, the writers followed the experiment to its logical, and apocalyptic, conclusion. By the end of the season, Bubbles wanders through a free zone that has turned into a Hieronymus Bosch painting: fires burning, bodies in doorways, women being raped, children running in unsupervised packs. To get the scene right, said Pelecanos, “we shot for two days straight, just to make sure everybody looked really fucking tired.”

  Said Burns, upon seeing the final scene, “All we did, basically, was take the walls off the houses in Baltimore. That’s the shit going on inside.”

  • • •

  Finally, season three would both refocus on the Barksdale regime and chronicle its ultimate downfall, accompanied by the rise of the “New Avon,” as Pelecanos’s notes from Tarrytown had it. (Later, he added the name of the “New Avon”: Marlo.) And, as important: “Stringer Bell—Killed by Omar or B. Mouzone.”

  To be an actor on a TV show during the Third Golden Age was to live in a permanent state of anxiety, one’s mortality (and unemployment) forever lurking around the next plot twist. For some, death was just the beginning of a long, fruitful run of ghost and dream sequences. Most, though, understood that one of the period’s signature tropes—that, as in life, anybody could check out at any time—had significant implications for their job security. Even James Gandolfini admitted that he didn’t sleep entirely easily knowing that Tony’s fate lay in David Chase’s hands.

  The situation turned actors into forensic Kremlinologists, deep-reading every set of new pages for the slightest hint of impending doom. “Every time you read the script, you’re looking for a hint: if too much of your story is being told, ‘Oh shit, they’re building it up. I’m gonna go,’” said Andre Royo. He and Michael K. Williams decided between themselves that one of their two characters, either Omar or Bubbles, was bound to buy it before the series ended. (Williams won that Pyrric victory.) After a few seasons, Royo even developed a kind of Stockholm syndrome. He went to Simon and asked whether keeping Bubbles alive wasn’t a disservice to the story’s realism, given the usual life span of a junkie snitch.

  “David looked at me and was like, ‘Shut the fuck up,’” he said. “‘I don’t know what’s going to happen, but I do know there has to be some hope or people aren’t going to get out of bed in the morning.’”

  The Wire actors’ anxieties may have been compounded by the fact that communication with actors wasn’t foremost among Simon’s showrunning skills. “David had a problem about telling people how they were gonna die. He’d never just say, ‘Look, you’re gonna die.’ There was always this weird energy,” said Royo. Larry Gilliard Jr., who played D’Angelo Barksdale, had been infuriated by how he learned about his early departure in season two: Simon had run into him on set and said, “You’re going to love the stuff I wrote for you this episode.” “Great!” said Gilliard. “I mean, it’s probably your last episode . . . ,” said Simon.

  The lesson went apparently unlearned by the end of season three. By all accounts, the producers honestly meant to sit down and talk with Idris Elba about the timing and manner of Stringer Bell’s death. Instead, that meeting never happened, and he learned about it by reading the script—and subsequently hit the roof. Making things worse was the script direction that had Omar standing over Bell’s body and urinating on it, apparently a real Baltimore gang tradition. Elba headed to the set and started telling fellow actors he wouldn’t shoot the scene, enlisting some in his cause.

  “He was pissed, man. And I got it, because, in effect, we were firing him,” said Pelecanos, who wrote the episode. “David and I went to his trailer and tried to talk him down. We said, ‘This is the end of the character. We can’t keep his story going, it’s not logical. And this is exactly the way he would probably go out.’” Elba fixated on the pee. Omar wouldn’t be peeing on him, Simon and Pelecanos said; he’d be peeing on a fictional character. “Not on my character,” Elba told them.

  Simon and Pelecanos could have invoked a favorite David Chase line when faced with similar protests: “Whoever said it was your character?” Instead, they cajoled and apologized until Elba relented. The death scene was shot at an empty Baltimore warehouse and wrapped at four a.m. On his way down a dark street to his car, Pelecanos heard pounding footsteps behind him and turned, cringing. It was Elba. “I just want to shake your hand,” he told the writer. “It’s just business.”

  • • •

  The Stringer Bell controversy was an instance that would have benefited greatly from the equanimous presence of Robert Colesberry, but he was no longer there to provide a diplomatic, even keel. In January 2004, just before filming on season three was about to start, Colesberry had gone to the doctor to see about a procedure for a chronic throat issue; he had problems swallowing and would occasionally choke on food. While there, tests revealed severe arterial blockage and an emergency double bypass was ordered.

  Before going in for the six-hour operation, he talked about The Wire with his wife, Karen Thorson, who supervised the making of each season’s main title sequence. Colesberry spoke excitedly about using the Blind Boys of Alabama to record season three’s version of the Tom Waits song “Way Down in th
e Hole.” The last thing he said to Thorson was that they needed next to turn their attention to a sound track for The Wire, collecting all the music the show had employed over the years. (Like The Sopranos, the show didn’t use a score.) Then he went off for the routine surgery.

  The surgeon, Thorson remembered, emerged from the procedure confident that all had gone well. Then, at one a.m., she received a call. “They said, ‘We want to do an MRI, because he’s unresponsive.’ They said it like they were delivering a newspaper: ‘Robert’s unresponsive,’” she said. Colesberry, it turned out, had suffered a stroke. Over the course of the next four days, he swam in and out of consciousness. Simon, Nina Noble, editor Thom Zimny, and members of the family gathered in the hospital room. Simon brought in a boom box and played fifties R&B and music from the show. On February 9, with the whole group gathered around his bed, Colesberry died. He was fifty-seven.

  There were several official memorial services for Colesberry, the last of which was held in Baltimore just before shooting began. Simon addressed cast and crew, assuring them that the production would soldier on. Many said it was a crucial moment for Simon, the point at which he ceased to be a journalist working in TV, or even just a TV writer, and became a full-fledged producer in the best sense of the word. There were implications for other members of the team, too. Pelecanos and Burns were given more responsibility, with Burns assuming the title of executive producer. Nina Noble, whom Colesberry had mentored for many years, stepped into his shoes and would be a crucial partner for Simon for the rest of The Wire’s run and beyond.