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.