Late Night with Conan O'Brien (1993-2009)

In the hubbub of last week, as the film community geared up for the Oscars, I failed to pause and say goodbye to one of the television staples of my adolescence and young adulthood. After fifteen-and-a-half years, Conan O'Brien signed off at Late Night, where he hopped and spun and jumped and yelled gibberish and ran and attacked the camera weeknights at 12:30 a.m. In college, my roommate and I had the best nighttime lineup two dry-witted, satire-loving, pop-culture-consuming cynics could hope for: Jon Stewart at 11, Dave Letterman at 11:30, Conan O'Brien at 12:30. By 1:30 a.m., fully put down in a hazy stupor, it was lights off.

It was somehow fitting it was these three men — New Yorkers, dead-panners, re-inventors, trailblazers all — could come sequentially. Their career paths have overlapped considerably: When Letterman left Late Night in 1993, after yucking it up with watermelons thrown from rooftops and stupid pet tricks galore, both Stewart and O'Brien were considered as replacements (and both continually give reverence to Dave whenever possible); then when O'Brien was announced as the new host of The Tonight Show (which Letterman never got), Stewart was bandied as a possible replacement for O'Brien. Their paths crossed numerous times, and sometimes in my mind their gags and jokes would become misidentified. But there they always were: the political eviscerator, the self-deprecating boomer, the frantic fool.

When it was announced in 2004 that O'Brien would join the The Tonight Show after Jay Leno's retirement, it was never a concern of mine that they would be a bad match. I'd watch O'Brien do a morning show, an afternoon show, a radio show, whatever — the success of a host-oriented program is based more in the personality of the host than anything else, otherwise Letterman, whose Top Ten Lists ceased to be funny more than a decade ago, would have fallen off the radar by now. What disappointed in the moment was that an O'Brien move would be the dissolution of the Stewart-Letterman-O'Brien trinity, which had already begun falling apart when Comedy Central debuted the genius Stephen Colbert in his own show at 11:30, and that became a more frequent destination for me than Letterman.

It's said that O'Brien's humor appeals to a younger demographic, but I'd venture a guess that the youth of his audience had more to do with his time-slot than any inherent comedy stylings. O'Brien, after all, was a Harvard graduate, a veteran of the Harvard Lampoon satire magazine, and a former writer for The Simpsons and Saturday Night Live — nothing, I'd say, that immediately disqualifies him from being able to induce chuckling in a boomer. It was easier in college to watch O'Brien knowing I didn't have to wake up until 10:30 in the morning; once I entered the workforce (but before the introduction of DVR), it became substantially more difficult to watch him.

Still, it would be naive to discount how a specific time-slot and the evolution of humor possess a symbiotic relationship. Comedy tailors itself, whether consciously or unconsciously, to its audience, and an audience seeks out, whether consciously or unconsciously, a specific brand of comedy. After nearly sixteen years in the Late Night hour (where Letterman had previously flourished before making a big move to opposite The Tonight Show), it's difficult not to think of Conan's audience as a certain demographic and Conan's humor as a particular brand, but it would be equally naive to think that an entertainer can't evolve to the conditions around himself and not change the core of his being. I have faith in him based solely on his intelligence, which during the run of Late Night skewed his show to riskier recurring (and some might say more ridiculous skits, such as If They Mated, The Walker Texas Ranger Lever, the talking lips screens, and The Year 2000, which continued long after the new millennium began. Who else could hone in on the irony in a person's image and exploit it to such great laughs, as in Apple-Picking with Mr. T? Who else would broadcast a rerun of a show but done entirely in claymation?

Letterman's stint as Late Night host, before being dissed by NBC for The Tonight Show, holds a place in the hearts of many in the generation immediately preceding mine. Time magazine's list of the 100 greatest televisions in the history of the blinking-tubes-in-a-box includes Late Night with David Letterman (at 12:30) but not The Late Show with Daivd Letterman (at 11:30). Why? "Letterman at his best gives you the feeling of being lucky enough to watch him play with this awesome toy he's been given." That's how I feel with Conan; his Late Night means to me what Letterman's Late Night meant to others. But it strikes me as if Conan, plucked from obscurity when Lorne Michaels pushed heavily for him to take over Late Night, will always be a boy with an awesome toy, and yes, The Tonight Show will be different, but in as long as I've been actively watching television, I've never liked The Tonight Show. His transition into host comes at the right time for me, as I transition.

It's strange how that happens, how our everyday and individual lives can become connected to the world and charted through certain technologies. Perhaps it's a strange way to think of it, but O'Brien leaving Late Night informs me more on the subject of my age than it does anything else. Individuals and societies can trace their growth through their art (in this case, late night comedy), which must reinvent and rearrange itself regularly to stay alive. Something that was always a mainstay for my college years — Stewart, Letterman, then O'Brien, in that order, Mondays through Thursdays — isn't anymore. More than my own new jobs, my wonderful marriage, my relocation and a jumbling of where I call home, more than anything, it's when something that was always there, something you took for granted, begins to unravel that you realize the past is really in the past. It was fun while it lasted, but who's to say new fun isn't around the next corner?