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

by Brett Martin

  There was one more memorial to come. In the third episode of season three, a wake was held, in accordance with Baltimore police custom, at venerable Kavanaugh’s Bar. Ray Cole, the character Colesberry had played, was laid out on the pool table. It was Dennis Lehane’s episode, but Simon wrote the tribute delivered by the character Jay Landsman. In it, Landsman praises the work Cole did “on that arson down in Mississippi” and “that thing on Fayette,” references to Mississippi Burning, which Colesberry produced, and The Corner. Finally, he concluded, “Ray Cole stood with us. All of us. In Baltimore. Working. Sharing a dark corner of the American Experiment. He was called. He served. He is counted.”

  Before filming started, Thorson and Simon had taken Colesberry’s ashes in a piece of Tupperware and, with a plastic spoon, spread them around the sets of The Wire.

  • • •

  With the third season completed, HBO certainly had every reason to feel it had done right by The Wire: it had allowed the show to run for thirty-seven episodes, despite small ratings and few awards. Now the story that had started it all, the effort to bring down Avon Barksdale and Stringer Bell, had played itself out. From a business standpoint, it was hard to argue that it was owed any more time or space.

  But then, of course, hard arguments were David Simon’s chosen art form. He and Burns had already sat down and discussed ideas for two more seasons. Burns was intent on visiting the public school system, to explore the world he had experienced as a teacher. Simon, in turn, had always believed that the only proper ending for the series would be to turn The Wire’s roving gaze on the world he knew best: the press.

  “The last critique we wanted to make was of ourselves, our media culture,” he said. “It was a critique of newspapers, but it was also a critique of the audience, of how stupefied and simplified the audience has become. So that Americans can no longer recognize their own problems, much less begin to solve them.”

  Later, rumors surfaced that a sixth season, focusing on Hispanic immigration, had been scrapped, but Simon dismissed them. A season on that theme had been proposed by David Mills, he said, but it would have needed to be inserted before the events of the fourth season, which led to the series finale, were put in motion. It would also have required everything to stop so that the writers could do the research necessary to maintain the show’s level of verisimilitude. And time was one thing Simon did not have, as he tried to save his show before it was scattered to the wind. Already, in the long hiatus, uneasy actors were investigating other jobs; Andre Royo went deep into the audition process to play “Crab Man” in the NBC sitcom My Name Is Earl.

  Simon and Burns sat down and worked out a story that focused on four elementary-school age boys losing their innocence in various heartbreaking ways as the season progressed. We would be introduced to them by the ex-cop Roland Pryzbylewski, who, like Burns, had left the force in order to join the public schools. (There had been a time, during the brainstorming for season three, when the character of Carver had been the one the writers pointed toward becoming a teacher.)

  Then Simon marshaled all his powers of persuasion: the tantalizing storytelling, the moral dudgeon. And the begging. “I don’t mind kissing ass when the ass then moves and does what it’s supposed to do,” he said. “Give me that familiar HBO ass and I’ll pucker right up.”

  Every time The Wire had come up for renewal, Chris Albrecht remembered, the HBO fax machine would leap to life. “David would send these letters—intense, single-spaced, pages long—explaining why picking up this show was something we absolutely had to do. You would get to the third page and be so exhausted you’d say, ‘Just tell him to come in.’”

  Carolyn Strauss had always considered The Wire a favorite child—or at least the one most in need of protection. “I suppose it was because The Sopranos got all the attention,” she said. “And my little baby did not.” Still, she knew that more seasons would be a tough sell and which way the wind was blowing. “I understood the business pressures that Chris was under. And I knew it would be a painful decision.”

  Said Albrecht, “We had taken the show to three seasons. Season three had ended in a great place. Arguably, the story was complete. So, let’s declare victory for a show that nobody was watching—and not a lot of people were writing about, either—and move on.” On the other hand, he was willing to hear Simon out. “We didn’t shut the fax machine down. We didn’t refuse him entrance to the building.”

  Instead, Simon was summoned to give the pitch of his life. Characteristically, its theme was less about the specifics of the proposed season four story than about a singular artistic appeal: he wasn’t done, he had more to say. When Simon left, Albrecht turned to Strauss. “He was like, ‘We’ve got to do this,’” she said. “And I was like, ‘Duh.’”

  “It was one of those meetings that played out as you would’ve hoped,” said Michael Lombardo, then the executive vice president of business affairs, production, and programming operations, who was in the room. “A passionate, smart writer gave a beautiful explanation of what he was wanting to do, and the network responded appropriately. Chris listened, understood, and responded. I was very proud of him. It was a good day to be at HBO.”

  “Honestly,” said Albrecht, “I think it was easier to do the fourth season than to have to call up David and have another meeting.”

  • • •

  Production on season four was, Nina Noble said, the high point of the near decade of The Wire, despite being a flagrant violation of the old show business imprecation against working with children or animals. “Just personally, for David and me, we had spent the third season still trying to deal with Bob’s death and figuring everything out. The fourth season was really when we felt like we were standing on our own again.”

  The kids were not the only thing different about season four. Dominic West had been growing increasingly restless. With a new baby back in London, he was putting his wilder days behind him, and it was hard to be an ocean away, occupying the same head space as the hard-drinking, skirt-chasing McNulty for yet another season. There were also the temptations of bigger stages. Almost alone among The Wire actors, West had become moderately famous thanks to the show. There were murmurs about his becoming the next James Bond.

  For all these reasons, West had asked to be put on the back burner for season four. The previous season had ended with McNulty busted down to beat cop and happy about it. That’s where he remained for most of season four, seemingly done banging his head against the police department’s walls and shacked up in domestic bliss with the harbor policewoman Beadie Russell.

  Still, West was needed for at least brief scenes in every episode, and the production often tied itself into knots attempting to accommodate his schedule—often cramming scenes from several different episodes into his visits to Baltimore, about a week per month, so he could hurry back to London. This was already causing some stress among what was usually a strikingly peaceful ensemble. When West began showing up unprepared and grumbling, his fellow actors felt it was time for some self-policing. A group of them—Sohn, Royo, and Gilliam, and others—rented a hotel room and staged a gentle but pointed intervention.

  “They wanted to tell him, ‘Look, get with it. When you’re here, you’ve got to be here,’” said Noble, who didn’t hear about the meeting until after it was over. “It’s the kind of thing that I would have had to do eventually, but they just took care of it.” West, she said, shaped up quickly.

  Unlike other seasons, this time the production had the luxury of shooting all twelve episodes before any began airing, which made things at least marginally less stressful. (Simon’s production company, went a quip popular with nearly everybody who knew him, was called “Blown Deadline” for a reason.)

  The schedule was helpful in another, vital way. By now, the revolution in viewing options was well under way. In 2001, HBO had launched its on-demand service. The next year, DVD sales eclipsed VHS for the fi
rst time; an industry report cited the release of entire seasons of The Sopranos and other TV shows as one of the driving factors in the technology’s growth. Meanwhile, TiVo and other digital video recorders had made their debut, further detaching any given program from any particular night.

  The network now brought some of those changes to bear on its last-ditch attempt to build The Wire’s audience. The three previous seasons were released in DVD sets. Meanwhile, critics received all thirteen episodes of the new season and were asked to watch it in its entirety before it even began to air. This was a tacit admission that one of the strengths of the new TV—the ability to draw out stories as if in a novel—could also be a weakness: it could take three or four or five hours of viewing before the show became addictive, just as you might need to read one hundred pages of a novel before getting hooked. This had been a particular problem for The Wire, which with its complicated jargon and byzantine plotlines gave even less quarter than most when it came to easing a viewer in. The biggest obstacle lovers of the show faced when trying to recommend it to friends was dislodging the suspicion that it was homework, TV that was good for you but not at all a good time.

  Critics had always been kind to The Wire, if not overtly messianic (this was before the era of twenty-four-hour tweeting and recapping). After watching season four, they began beating the drum in earnest. “This season of The Wire will knock the breath out of you,” wrote the The New York Times. “This is TV as great modern literature, a shattering and heartbreaking urban epic,” said TV Guide. James Poniewozik, in Time magazine, wrote, “They have done what many well-intentioned socially minded writers have tried and failed at: written a story that is about social systems, in all their complexity, yet made it human, funny and most important of all, rivetingly entertaining.”

  To further entice people to watch, HBO confusingly began to offer future episodes for on-demand viewing, almost immediately after a previous episode had aired. This may have felt somewhat desperate, and it undercut some of the sense of occasion that longtime fans felt as Sunday night approached, but it did allow more viewers the chance to find their way to the show. Certainly, something worked in its favor: the average weekly rating for season four was, depending on whose numbers you trusted, somewhere between 4.4 and 5.5 million viewers, up dramatically from 3.9 million during season three. That was still a shockingly small number by the standards of mass media. But a better measure was the degree to which The Wire suddenly penetrated nearly every conversation among a certain class of educated, liberal, city-dwelling HBO viewers. Legions of these now scurried back to watch the first three seasons while taking in the fourth in real time, making the series perhaps a unique instance of a narrative experienced out of order by a majority of its viewers. In some circles, to not have seen The Wire had become a shocking breach of social protocol.

  • • •

  For these, among other reasons, perhaps the deck was stacked against The Wire as it moved into season five. For many involved, there was a palpable sense of having peaked.

  “I thought that no matter what we did after the kids’ story was going to suffer. Emotionally, you weren’t going to top that,” said George Pelecanos.

  HBO, too, seemed to think that the best was over and it was time for a denouement. The network had committed to doing one more season, but it was adamant that it be shorter than the previous three. Simon pitched hard for the usual twelve or thirteen episodes, but HBO stood firm at ten.

  Under any circumstances, this would have been disruptive. Twelve or thirteen one-hour episodes had proven over the past half decade to be organically, almost magically, well suited for the telling of certain kinds of stories. By some accounts, the number thirteen was merely a fortuitous holdover from the days of twenty-two-episode seasons, when networks would order that many episodes to start and then another nine on the “back-end,” if all went well. David Milch had a more numerological explanation for the use of twelve, which became the alternate standard for HBO shows after The Sopranos:

  “To the extent that the corollary theme is what we learn or fail to learn over the course of time, then form and content inform each other. So twelve, which is formally just an attribute of the calendar, becomes a thematic principle,” he said, also noting that days consist of two twelve-hour halves.

  Whatever the underlying reason, the new genre of drama seemed invariably to lose its way when its usual rhythm was disrupted—either by a shortened season or lengthened double episodes. The pacing would seem off, the storytelling judgment flawed. Since even in a full-length season The Wire would have more story than the allotted time would allow, being limited to ten episodes was bound to be an issue.

  And Simon had plenty to say—a decade’s worth of fuming passion about where his beloved Baltimore Sun had gone wrong. In particular, he took aim at two star editors, John Carroll and Bill Marimow, who had taken over the Sun in the early nineties. The outsiders, to Simon’s mind, had instituted a corrupt and cheapened culture more concerned with winning Pulitzers than serving the community—or, for that matter, getting things right. In 2000, Simon had denounced a Sun reporter, Jim Haner, in the magazine Brill’s Content. Haner, a prize-winning star at the paper, Simon charged, repeatedly embellished and perhaps fabricated stories, while Marimow and Carroll looked the other way. For his trouble, Simon was painted as an angry, vindictive ex-employee. Now, with more visibility at his command, he revisited the same turf, creating a fictional Baltimore Sun led by imperious, detached editors and harboring a serial fabulist.

  Underpinning the story, beyond whatever grudges were being worked out, was a serious point about how the media is fatally detached from the reality it purports to cover. This, to Simon’s mind, was the final piece in the big “Why” of The Wire. It was summed up in one scene, perhaps the best of the season, when Omar, who had loomed so large throughout the previous fifty-seven hours of the show, a walking myth whose name literally rang out as he walked down neighborhood streets, failed to merit even a mention in the city’s paper of record when gunned down. Even to the reporter and editor whom Simon clearly admires, he’s just another “thirty-four-year-old black male, shot dead in a West Baltimore grocery.”

  It was an elegant, devastating scene, one that said everything about the two radically different worlds inhabited by the show’s rich and poor, black and white, powerful and disenfranchised characters, and about the futility of ever bridging the divide between them. Unfortunately, there was much more newsroom plot. The simple truth was that in several important ways, season five was a failure, dramatically. All of the concerns Simon’s fellow writers had in previous seasons about new characters and story lines crowding out old ones came true: Pelecanos’s ex-con Cutty was all but gone. Pryzbylewski, gone. Two of the four kids from season four, gone. And so on. Only this time the losses came without the compensatory pleasure of rich, three-dimensional replacements. Simon’s newsroom felt schematic, its villains too obviously evil, its heroes too ruggedly saintlike. (Even the name of the fabricator, Scott Templeton, was a ham-handed reference to the rat from Charlotte’s Web.) Many devotees, watching the shortened clock run out on this universe they had come to love, couldn’t help resenting every minute spent in the company of these interlopers. And the characters’ woodenness planted a seed of doubt in those for whom the newsroom was the most familiar of The Wire’s worlds. If he’s this wrong about these guys, the thinking inevitably went, maybe he was wrong about all those other guys, too.

  In the writers’ room, oddly, there was more dissent about a different story line: one in which McNulty (reactivated for this final season), in a final, desperate effort to direct the department’s energy toward the drug infrastructure, invents a false serial killer. Simon had been toying with the story for many years; it had started as part of an aborted novel he had begun to write as far back as 1996 and of which he had completed one hundred pages. The plot would not seem to be any more of a radical departure from reality than Ham
sterdam had been, but it was the cause of much conversation both in the writers’ room and among viewers who felt it finally exhausted their suspension of disbelief.

  All of this led to something unique in the history of The Wire: a chorus of bad reviews. “What Happened to Our Show?” pleaded the title of a representative essay in the Washington City Paper. “Simon may yet right the ship,” the article read, but The Wire was “thudding to a close, stuck in a stereotypically TV-like world it’s heroically avoided until now.”

  Simon did not respond to the criticism with grace and stoicism. In fact, he created an angry and airtight syllogism: If the media had a problem with season five, he said, it was because they felt threatened by its critique of the media. It was, necessarily, a matter of thin skin. (Never mind that the degree of association between modern TV critics and traditional hard-news journalists of the type he was portraying was slight, at best.) His lengthy lectures on the subject to anybody who raised an objection were successful in drowning out more substantive criticism of the season’s artistry, but it was hard not to feel that the argument would not have passed muster at the Simon family dinner table in Silver Spring.

  How did it happen? How did such an acute and assured show lose its way in its waning moments? One popular answer was that Simon was too close to the material, that his judgment was impaired by the strength of his lingering resentments. But Simon himself seemed to nail a more subtle diagnosis. He was talking about the role he had played in season four, when Burns was intent on critiquing the school system: “Everybody, if they’re trying to say something, if they have a point to make, they can be a little dangerous if they’re left alone,” he said. “Somebody has to be standing behind them saying, dramatically, ‘Can we do it this way?’ When the guy is making the argument about what he’s trying to say, you need somebody else saying, ‘Yeah, but . . . ’”