Conan O'Brien's Late Night Legacy Was Born By Breaking Late Night Rules
A fresh-faced comedian walks through New York after having woken up and feeding his fish. He's got a nearly beatific smile on his face as he's wished good luck and almost instantly told by those same people (with sarcastic tones) that there's no pressure, because he's been chosen to replace one of the most beloved comedians to ever grace the small screen. He's tall, lanky, with a shock of red hair, and he's just barely reached the age of 30. Everyone from John Tesh to Tom Brokaw to passers-by give him some version of these remarks ("Ya better be as good as Letterman!"), and he takes them all in good stride. He walks into 30 Rockefeller Center, gets ready for his first TV hosting gig, taking over the "Late Night" show on NBC at 12:35 am. He walks into his dressing room, where he proceeds to attempt hanging himself. It's only when a producer calls him out to start the job when he takes the noose away from his neck.
This is how Conan O'Brien started his late-night career: With an instantly brilliant, fourth-wall-breaking sketch that would serve to establish a foundation that lasted him through nearly three decades of television history. Though O'Brien was already an immensely talented writer, his on-screen career truly kicked off thirty years ago tonight, with the airing of his first episode of "Late Night with Conan O'Brien." In the intervening decades, O'Brien's status in late night shifted from struggling neophyte (one whose early years on NBC were often held up by weekly contracts as the network debated canceling him) to beloved but embattled icon (when the network that allowed him to flourish chose Jay Leno and his bland hosting style and paid O'Brien tens of millions of dollars to leave for good) to elder statesman. When he left behind his TBS show "Conan," O'Brien had been a late-night host for 28 years, and the remaining hosts left in his wake all owe self-professed debts to his unique style.
A smiling secret weapon
In some ways, Conan's distinctive late-night style was rooted in old-fashioned television formats. One of the most familiar bits on "Late Night," in which writer and performer Robert Smigel would impersonate celebrities such as Martha Stewart and Arnold Schwarzenegger (his lips superimposed on a still photograph of the celebrity in question), was inspired by the late-1950s animated series "Clutch Cargo," which utilized similar technology for its characters. But one of the strengths of each of O'Brien's shows ("Late Night", his all-too-brief tenure on "The Tonight Show", and "Conan") was how he, sidekick Andy Richter, and his writers would take perceived rules of television and flip them on their head, feeding into all sorts of sketches and recurring bits, from the "In the Year 2000" series, to characters like Triumph the Insult Comic Dog, to "audience members" like Andy's little sister Stacy (performed by a pre-"SNL" Amy Poehler).
That big smile of O'Brien's was also a secret weapon, because unlike Letterman (or the similarly revered Johnny Carson), he rarely displayed visible disdain for the vagaries of late-night entertainment. He always struck a careful balance, in remote segments or celebrity interviews, of showcasing some sense of Gen-X irony without being so dismissive as to make the audience not care. Most important to the idea of being able to bend or break the standard rules, O'Brien was quick on his improvisatory feet. Any fan of Conan's likely knows one of his very best celebrity interviews by heart: The 1997 appearance of "Melrose Place" actress Courtney Thorne-Smith, who had just wrapped her role in a Carrot Top comedy and was joined on the couch by the brilliant and sadly departed comic Norm Macdonald. Though O'Brien initially tries to be playfully flirtatious with Thorne-Smith, it's Macdonald's wry interruptions that quickly take over, with everyone climaxing in paroxysms of laughter as Macdonald says the last word of the film's title — "Chairman of the Board" — ought to be spelled "bored" because ... well, it's Carrot Top.
OK with being the butt of a joke
O'Brien's ability to laugh at himself, as much as at others or with others, was another key strength of his multiple decades of TV-hosting work. (It's the same with his immensely popular "Conan O'Brien Needs a Friend" podcast.) Especially after Richter left "Late Night" in 2000, O'Brien would enable himself to become the butt of a joke, whether in a mid-interview scripted gag where he and guest Julia Louis-Dreyfus steal Tina Fey's most recent Emmy, or in his run on "Conan" where one of the most popular recurring characters wasn't a character at all, but his assistant Sona Movsesian, who often seemed to excel at doing everything but her job duties. (A wonderful example of their hilarious dynamic is in a remote segment in which Conan meets and interacts with a handful of his interns, learning that she ordered lunch for herself but used his name to get the food faster, and that she's dropped his name in less flattering contexts to get the interns to do her busy work for her.)
Perhaps the most memorable stretch of O'Brien's TV run wherein breaking the rules was required occurred the last time the Writers Guild of America went on strike, from November 2007 into February 2008. O'Brien, like many other hosts, took his show off the air for a couple months, but went back to work in January 2008 to ensure the rest of his staff wouldn't struggle. But in solidarity with the WGA, he had no writers with him, ironically resulting in one of the freshest, funniest periods of his career. He was nearly 15 years into his run on "Late Night," and had already agreed to take over "The Tonight Show" by this point, so it's no surprise that O'Brien was immensely comfortable in front of a live audience. But the looseness of these episodes ended up serving as a new chapter in his career. (And, as evidenced from a fan upload of his first opening section back from the strike, it was just incredibly funny to watch him do something as simple as spinning his wedding ring on his desk.) Crucially, it was this period when Conan leaned further into introducing the audience to members of his staff. If it wasn't for this period of O'Brien's career, how well would his fans know, for example, his extremely oddball and funny and stoic associate producer Jordan Schlansky?
A Millennial icon
Even though O'Brien came up with Generation X, his brief time on "The Tonight Show" and the remarkably stupid ways in which NBC shot themselves in the foot in failing to support him highlighted that he hit hardest with Millennials, those who grew up with him the way he grew up with Carson. The massive fan outreach in January 2010 (like the "I'm with Coco" campaign), followed by his incredibly funny live show that occurred in between his departure from NBC and his arrival on TBS, made it very clear that just as David Letterman had become a cultural icon to a certain generation, O'Brien too had tapped into a comic sensibility that resonated with the generation after his own.
So many of the most memorable segments on his late-night programs reflect that sensibility and why it works so well. Some of it amounts to breaking the fourth wall either by design or by accident (when a bit might stumble, or if — in one case — Richter inadvertently broke a couch leg so that O'Brien could playfully ask rhetorically, "What kind of crappy show is this?"). Some of it involves biting the corporate hand that feeds you. Leaving aside Conan's final week on "The Tonight Show," where he pretended to spend exorbitant amounts of money on bits that weren't so much funny as costly to his soon-to-be-former corporate overlords, some of his best bits either mock his own network or various businesses that enable him to talk about their products without exactly being flattering.
The student has become the master
Conan O'Brien left a daily talk show behind in 2021– even before the COVID-19 pandemic hit, he'd scaled back his own show to be a 30-minute program with a single celebrity interview as opposed to the hour-long installments he'd done for decades. But he hasn't left the airwaves, both because of his wildly popular "Conan Without Borders" series that has transformed into the upcoming Max series "Conan O'Brien Must Go." And his aforementioned podcast is one of the very best of the medium, highlighting that over time, he became one of the best and most gifted interviewers on television.
Because of the dual strikes going on in Hollywood, none of the late-night shows are on the air right now with new episodes. But coincidentally, a number of those same hosts have a podcast of their own, "Strike Force Five," in which they share what they've been up to and what stories they wish they could've covered had the strikes not occurred. None of the men hosting that show — Jimmy Kimmel, Seth Meyers, John Oliver, Stephen Colbert, or Jimmy Fallon — are new to their roles, and Kimmel just marked two decades of hosting earlier this year. But it is hard not to listen to that show and think that they all follow in the footsteps of a true legend. Three decades ago, Conan was the one being warned that he'd have to be as good as his predecessors. Now that he's away from daily TV, Conan's influence only seems greater; his contemporaries continue to have to live up to him.