Former Late Show Head Writer Donick Cary Reflects Upon His Days with David Letterman

Courtesy of Donick Cary/Donick Cary on the set of The Late Show with David Letterman.

Writer Donick Cary on the set of The Late Show with David Letterman.

By CHRIS KAZARIAN

A bear walks into a strip club… 

This sounds like the set up to a bad joke, but 21 years ago it served as something more absurd – a skit for the Late Show with David Letterman.

Inside the bear costume was staff writer Donick Cary. The costume, and the show, have particular significance for the veteran comedy writer and producer.

First, the outfit. Cary was not unlike the rest of the Letterman crew – stage manager Biff Henderson, announcer Alan Kalter and costume designer Sue Hum – whose titles are only partially accurate. “It was all hands on deck,” Cary said earlier today, meaning that crew members were often called into action, becoming part of Letterman’s zany cast of characters.

So when producers needed someone to be in a bear suit, Cary jumped at the chance. The essence of the gag was simple, and very Letterman-esque, meaning that Cary would find himself in hilariously precarious positions. “They had me see if I could get into a taxi and wandering down the street in the bear suit,” he recalled. “I stole a pumpkin from a deli and the owner almost shot me.”

In a case of life imitating art, the weirdness only continued when Cary was backstage in the green room before a show with first lady Barbara Bush and Dallas Cowboys running back Emmitt Smith. “We had a very weird discussion about how I was a lifelong Redskins fan and I didn’t care much for the Cowboys,” Cary laughed. “They were like, ‘Why would we care what you think? We’re both from Texas and we love the Cowboys.'”

The entire time, Cary was in his bear suit. Realizing he was probably not the best host for the two guests, he quickly made a beeline to the alley outside the Ed Sullivan Theater. “As I was standing there a cute girl came up to. It was Paul Shaffer’s new intern,” he said. “She said, ‘So you’re the guy in the bear suit.'”

That cute intern would wind up becoming Cary’s wife, Kimberly Huffman Cary. This year, they will celebrate their 16th wedding anniversary, all because of a silly bear suit. “I don’t think she would have noticed me if I wasn’t in a bear suit in the middle of the show,” Cary said.

Letterman’s Late-Night Influence

Now, the show. As a kid growing up on Nantucket, Cary faced many long, cold winters that accompanied life on the tony island off the Massachusetts coast. So he turned to TV, finding a beacon of hope in a lanky, gap-toothed, late-night talk show host on NBC. “I remember thinking, ‘Oh my god, there is something happening every night at 12:30,'” he said. “I would go to school tired, asking my friends, ‘Did you see Pee-Wee Herman, Bill Murray or Elvis Costello last night?’ It got me through those long winters.”

As fate would have it, Cary would soon make the switch from ardent fan to late-night contributor thanks to his father Richard Cary’s involvement in the Nantucket arts scene. As founder of the Actors Theatre of Nantucket in the mid-1980s, the elder Cary was able to lure professionals to the island during the summer.

One of those happened to be the wife of former Late Night scribe Steve O’Donnell. The wife, took a liking to the 16-year-old Cary, eventually introducing him to her husband at a party on the island. “They were like, ‘Steve does something you watch every night.’ So I asked, ‘Who is he?’ and they told me he is the head writer of the Letterman show,” Cary said. “I couldn’t believe it… There was someone from Letterman you could meet and talk to. It seemed like an opening of some kind.”

That opening would occur a little more than three years later when Cary became an intern, spending two semesters on Late Night with David Letterman before landing a job as an executive assistant at HBO.

His experience at Letterman left a mark. “The writing staff seemed to be doing what I was doing in eighth grade: they would screw around all day, but they weren’t getting into trouble. They were getting paid for it,” he said. “I felt like I found my calling.”

Cary ultimately returned to Letterman about two years later, initially as a writer’s assistant before being made a staffer and eventually the head writer of The Late Show.

As Letterman prepares for his final show tonight, Cary reminisced about what his first television gig taught him. During a four-year period in his early- to mid-20s, Cary was “given so much responsibility and they had this real faith in you and let you run with stuff. It really taught you the ropes.” It essentially laid the foundation for his later work as a professional comedy writer and producer.

His favorite bits that he wrote are ones that epitomize why Letterman is so revered as a comedian. “There was an intern who looked like a frozen pea so I said, ‘Let’s put him in a pea costume and call him ‘The Late Show Pea Boy’ and he would run through the audience and throw frozen peas at everybody,” Cary said. “It didn’t make sense and I’m not sure who it was for. Then we had Marvin Hamlisch compose music for him… That’s what was so great about the show. It was so dumb. It was asburdist comedy – let’s get an Oscar winner to compose this and pretend it means something. I love that.”

At the age of 26, Cary left The Late Show for The Simpsons. His credits include serving as co-executive producer for New Girl and Parks and Recreation. Recently, he signed a two-year deal with CBS TV Studios; the first year he will work on the HBO comedy Silicon Valley as a consulting producer.

Though he has moved on from The Late Show, this past week has represented a trip down memory lane for Cary who has been trading old show photos with former colleagues and sending emails congratulating those still working on it.

Tonight, he will gather with about two dozen LA alum to watch David Letterman’s 6,028th show as he says farewell to 33 years in the business.

With the current late-night landscape, Cary believes audiences will be left in capable hands. “I think all of them are incredibly talented, funny, great guys who work really hard,” he said. “That is the biggest thing, being willing to put in incredible amount of hours to host one of those shows. When I watch them [Jimmy Kimmel, Jimmy Fallon, Conan O’Brien] they seem like variations of what Dave did.”

As for Letterman, Cary called him a comic mentor. “He was a guy who set the bar very high for what would go on his show,” he said. “He was trying to do something new every night. If we were doing another Top Ten list, we always asked, ‘How could we do it differently?’ We all knew we would not do it every night, but he always was trying to be smarter, funnier and fresher.”

One of his fondest interactions with Letterman occurred during the show’s transition from NBC to CBS in 1993. With over a dozen of weeks to prepare for the first episode of The Late Show, the writing team was able to churn out some of its best material. “The night before we went on the air, (executive producer) Rob Burnett and (writer) Jon Beckerman and I were looking at these video pieces and Dave was so happy. We were sitting up above Broadway, maybe around 1 am, and the offices had shut down and we watched all these videos and laughed really hard,” Cary said. “Dave had a big smile on his face. He had gotten what he wanted. It wasn’t The Tonight Show, but it was The Tonight Show. I remember that was one of the best moments, sitting there and seeing him actually satisfied because he was armed with a bunch of comedy he was confident in and excited about and he couldn’t wait to put it in front of America’s eyes.”

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