This Article is From May 20, 2015

No. 10: How to Leave Late Show With David Letterman; No. 9: What's Next?

No. 10: How to Leave Late Show With David Letterman; No. 9: What's Next?

David Letterman in a still from the show.

Gathered with her colleagues for one of the last times in the offices of the Ed Sullivan Theater, Jude Brennan, an executive producer at CBS' Late Show With David Letterman, was reflecting on how she started working for the host some 35 years ago.

Brennan, who has collaborated with Letterman on his short-lived NBC morning show, on NBC's Late Night and now on Late Show, explained that this kind of devotion was its own special calling.

"It's not just a job," she said a few days ago. "It's something else."

Here, Steve Young, a writer for Letterman since 1990, chimed in. "It's community service," he said, to knowing laughter from his co-workers.

On Wednesday, when Letterman brings down the curtain on his final Late Show broadcast, it is not just his own 33-year history in late-night television that is coming to a conclusion. His departure also ends the employment of his entire Late Show staff, including several people who have worked with him for 20 years or more. (Also Read: American TV Legend David Letterman Bids Farewell)

These dedicated veterans have built their careers - and grown into full-fledged adults, and raised children - all while working for one enigmatic if intensely loyal entertainer.

Since Letterman announced his plans to step down from Late Show in April of last year, these employees have had several months to try to reconcile their feelings of pride and their gratitude for him with the melancholy and uncertainty they personally face - all while continuing to produce the show.

They recognize that they have been part of something special. But they are not sure what to do next, nor do they understand how such an idiosyncratic group held together for so long.

Asked to summarize the decadeslong experience she and her colleagues have shared, Barbara Gaines, another executive producer, said tentatively, "Crazy people find each other?"

Gaines, too, can trace her lineage back to Letterman's NBC morning show, which ran for four months in 1980.

She said she was originally hired as a receptionist, by an associate producer who thought her typing "sounded fast." After the morning show was canceled, Gaines said she ran into Letterman, who was puzzled that she had not come with him to Late Night.

"He said, 'Hey, how come you're not working on the new show?'" she recalled. "And I said, 'How come I'm not working on the new show?'" Letterman quickly rectified this.

Other colleagues gained their tenure in similarly serendipitous ways. When Bill Scheft, a writer since 1991, had his decisive job interview with Letterman, he recalled: "The last thing I said to him was, 'I hear your softball team needs a center fielder.' And he says, 'We need everything.' I got hired the next day." Matt Roberts, now the "Late Show" head writer, started in 1992 as an intern, when his duties included having to run around the Metropolitan Museum of Art, in search of the popcorn magnate Orville Redenbacher, for his booking that evening.

(After a fruitless hour, Roberts said, "I was like, 'I couldn't find anybody - what should I do?' And they just said: 'Oh, get in a cab and come back. We found him like 10 minutes ago.'")

Over the years, they have seen Letterman deal with his highly publicized transition to CBS after losing out on NBC's Tonight show; with marriage and fatherhood; with quintuple bypass heart surgery; and with a sex scandal involving staff members that could have cost him his job.

They have also watched him evolve from a performer known for innovative and unpredictable comedy bits to a more contemplative monologuist and interviewer.

"It's microscopic course corrections, day by day, until you look up and go 'Wow, things have really changed,'" said Rob Burnett, who, since 1985, has been an intern, head writer and executive producer for Letterman, and now runs his production company, Worldwide Pants. "If Dave were still putting on a Velcro suit and jumping up on walls," he added, "I think it would be foolish."

No one was completely surprised the day Letterman gathered his staff members into his dressing room and shared his retirement plans with them. "The way he conducted himself, the way he announced his intentions, it made perfect sense," said Jerry Foley, the Late Show director, who has worked for Letterman since 1990.

Still, Paul Shaffer, who has been Letterman's bandleader and sidekick throughout Late Night and Late Show, said he had gone through a wide range of emotions this past year.

The initial question Shaffer said he asked himself was: "What am I going to do with myself every day? I haven't had to answer that question for 33 years."

He said that further feelings of sadness gave way to "a more Zen-like state."

"The only appropriate emotion is gratitude," he added.

Tellingly, no one interviewed for this article knew what his or her next job. (Young, the writer, said he was told that offices had to be cleared by the end of Friday to prepare for employees of Letterman's successor, Stephen Colbert, who arrive this summer.)

Young said that whatever he did next, "I would be a little reluctant to go into another five-day-a-week, office-setting-type job, at least right away."

"I'll try 20 things, hope one or two stick, and that will start me off somewhere," he said. In the meantime, he said, he would run "a thriving eBay business, selling junk from my office, for a while."

Brennan found truth in something she said Letterman had told her a few days earlier. "He said, 'Me and Paul, we knew how to start this show - we don't know how to end it,'" she recalled.

She added that she could not completely predict how she would react when something so central to her life was suddenly absent, and she had trouble envisioning what she would do next.

"I keep trying to imagine what it's going to be like when that last show is actually over," Brennan said. "And somehow, I can't figure it out. I can't."
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