The War for Late Night_ When Leno Went Early and Television Went Crazy - Bill Carter [35]
But Conan knew in his gut the show he really wanted to write for—the show that had so captured him with its comic sensibility that he cringed with regret when it was impossible for him to catch it every night when he was in college. Everything about what David Letterman was doing on his NBC Late Night show spoke to the creative core of Conan O’Brien, and he was spurred by the possibility that he could someday write for Dave and find ways to satisfy his jones to perform at the same time. His inspiration in that regard was Chris Elliott, the young Letterman writer who had become a regular performer on the show, creating off-the-wall characters, most memorably “The Guy Under the Seats,” in which he played a nutjob who lived beneath the seats of Letterman’s studio.
Conan finally put together a packet—a collection of comedy pieces based on what the show was then doing, including monologue jokes, material written for established sketches, and some the writer would invent—sent in his submission, and waited for the good news.
The wait was considerable, because writing openings on Letterman’s show were rare and, with a sizzling-hot show on their hands, the staff was flooded with submissions. But Conan’s packet eventually made its way to the top of the pile, and when the first opening in a long stretch came up, he learned he was in contention for the spot with just two other guys. One was a kid named Rob Burnett, who had been on the Letterman staff for a while as an intern, receptionist, and anything else he was asked to do; the other was an advertising copywriter from Oklahoma named Boyd Hale.
The show went with Hale. Steve OʹDonnell, the already legendary head writer for Dave—who had succeeded the equally legendary Merrill Markoe, Dave’s first head writer and also once his longtime girlfriend—called Conan with the bad news. O’Donnell, himself a Lampoon alum, told Conan, “Dave doesn’t want to go with another Harvard guy.”
The news devastated O’Brien—he had been that close to working for his idol. The disappointment lingered for some time, although it would be mitigated somewhat years later when Dave, after being reminded during an interview that Conan had almost been a writer for him, replied wistfully, “Well, our loss.”
Within months of that setback, however, he and Greg Daniels made it past another of television’s toughest cuts and were hired as staff writers for Saturday Night Live.
The show, by then just into its second decade and with Lorne Michaels back in charge after his self-imposed interregnum, had been the incubator for a generation of comedy talent, in both performers and writers. Landing there in 1987, with a new cast (Phil Hartman, Dana Carvey, Jon Lovitz) about to explode, Conan thrived, though the fit always felt imperfect to him. Something about what Letterman did, the everydayness of it, simply appealed more to him. At the same time, breaking through as a performer on SNL given the existing lineup posed a forbidding challenge. Conan wasn’t a mimic on the level of Carvey; he couldn’t create and lose himself in characters the way the phenomenal Hartman did. Conan knew that whatever part he might play in a sketch, his sheer Conan-ness would burn through.
What his SNL stint did accomplish was to expose his burgeoning writing skills to a critical group of contacts. Lorne Michaels, chiefly, made note of the new kid’s remarkable facility to write any kind of comedy and marked him as someone to keep his eye on. Conan was also slaying longtime SNL presences like Jim Downey and Al Franken with his spontaneous bursts of silliness. And he found a kindred spirit in Robert Smigel, a young writer with swagger who had been among the few to survive a staff purge by