Conan O’Brien is an incredibly smart man, and that’s one of the reasons his career in late night nearly died aborning. When he first started his own show, he was considered too smart. Too smart and too sophisticated. This was 1993, years before more Americans would start, as the bumpers twenty-odd years ago put it, getting more of their news from Comedy Central then probably should. Late night comedy basically gave you the choice between what has been described as David Letterman’s style of “anti-comedy” and the more Middle American comedy of Jay Leno. Conan O’Brien was definitely neither of those things.

Before that, of course, there was Saturday Night Live. Possibly the first time I ever saw him was playing Andy in the Twin Peaks parody. He wrote a few sketches and played a bunch of background characters, mostly. In 1991, largely because of burnout, he quit the show, where he went to work for The Simpsons instead. One of the things that is pretty well going to be in every epitaph of him is that he wrote “Marge vs. the Monorail.” He is credited with starting to take the show away from its original style of Just Another Family Sitcom and into the more surrealist family we’d come to know.

It is also worth noting that one of the four episodes IMDb credits him with is “Treehouse of Horror IV,” which is the one that features a play on “The Devil and Daniel Webster.” Because, as established, O’Brien is smart. Yes, he’s one of an enormous number of comedians to come through Harvard and National Lampoon. He is in fact the child of a Harvard professor of medicine and a retired attorney. He was an intern for Barney Frank. He won the National Council of Teachers of English writers’ contest his senior year in high school. And his Harvard thesis was Literary Progeria in the Works of William Faulkner and Flannery O’Connor, about the use of children as symbols in the authors’ works. A very smart man indeed.

In many ways, O’Brien is what I think of as a Funny Nerd. This is no shame; some of the greats of comedy are Funny Nerds. If George Carlin was a class clown, Stephen Colbert is clearly a nerd. He beat Peter Jackson’s on-set expert in a Tolkien trivia contest, after all. O’Brien’s knowledge informs his comedy; that’s one of the reasons he came so close to being canceled for most of the first few years of his show and one of the reasons he’s gained such a devoted following. It’s hard not to love someone who gets the same references you do, and O’Brien knows the same things as a lot of people.

Even silly bits that you wouldn’t think have that sort of thing are clearly built on Just Kind Of Knowing Stuff. “In the Year 2000,” a bit which only got sillier as time went on—I remember watching it in January 2000, just for starters—is clearly a play on the Criswell sort of psychic. There’s a lot of O’Brien references that are enormous amounts of fun that also have a great deal of knowledge behind them. By all accounts, O’Brien can’t help being funny. He needs it to feel complete. But how he is funny has a lot to do with how smart he is, and that’s one of the best kinds of funny in my book.

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