I'll admit I enjoyed some of his jokes and all of his filmed segments, particularly the "Would you like to buy a monkey" bit; between John Turturro's Burt Lancaster impression and Albert Brooks earnestly declaring, "I'm confused...I thought I was playing the monkey," I nearly laughed my way to a hernia.
But thinking about Letterman's prankish star turn afterward left a slightly bitter taste in my mouth.
Granted, at least Letterman was edgy and unpredictable, which counts for plenty on an Oscar telecast that ranked as the most sloppily produced, boringly conceived, and relentlessly predictable in recent memory.
Forget the dearth of sudden upsets or brilliant quips; these jokers couldn't read a teleprompter, time an entrance cue, or keep the camera straight to save their lives. Nearly everything that happened in that auditorium felt mistimed and inappropriate--especially Tom Hanks' teary-eyed Best Actor acceptance speech, a crude, canned spectacle that retrospectively cheapened his messy but sincere display of emotion at last year's ceremony. (Was it really necessary for him to declare that he was "standing on magic legs" and offer God's blessings to the entire world? To quote the late, great Paddy Chayefsky, a simple "thank you" would have sufficed.)
That's why the sight of a TV talk show host hijacking the film industry's biggest yearly shindig and turning it into a four-hour episode of "The Late Show" with an audience of one billion people was so refreshing--at least for the first hour or so.
It seemed like Letterman was poised to confirm what I'd long suspected about Oscar hosts: it's better to hire somebody from outside the film industry like Johnny Carson than an insider like Whoopi Goldberg or Billy Crystal, because while the insiders play primarily to the powerful folks inside the hall, the outsiders are more interested in pleasing the viewers at home.
But ultimately, Letterman failed to pull off the kind of delicate and gracious balancing act Carson routinely achieved without breaking a sweat; he failed to mediate between the insiders and the rest of us. For the alleged "host" of a glitzy shindig, he didn't seem very interested in what happened between his own appearances.
And his jokes and gags often betrayed an attitude toward the Oscars that bordered on contempt. By the time Letterman sabotaged Tim Robbins and Susan Sarandon's pre-scripted, pre-approved joke apologizing for their political mumblings of a couple of years ago (by declaring, "they're bound to be pissed off about something!"), the evening went from irreverent to eerily mean-spirited.
Just because you're smart enough to realize that an event or an institution isn't everything it's cracked up to be--that it's essentially dumb, artificial, trivial, or pointlessly hyped--doesn't mean you have to resolve not to love it. The joy of appreciating pop culture lies in the act of identification--of finding something resonant in a dumb, disposable piece of entertainment and embracing it.
If you can't bring yourself to do that because of intellectual, philosophical, or even comedic reasons, then you might as well quit and go live in the woods somewhere, because you're a soulless killjoy--the kind of person who goes to a party of his own free will, hangs around all night by the snack table, and gripes to any-one who will listen about how pointless parties are.
The sight of a smart man building his entire career around looking smug, impatient, and vaguely hostile gets mighty tired after a while. It can be amusing and occasionally hilarious when you build a nightly, self-enclosed postmodern comedy show around it, as Letterman does, but when you export that same attitude to unfamiliar soil, the results can backfire.
In one four-hour stretch, Letterman revealed himself as a woefully limited performer. I won't point out that his fame rests on not giving a damn about anyone or anything, because that's why a lot of people worship him. But I will ask whether anybody can truthfully say that anything substantive or even memorable was attained by his approach.
I doubt anyone can. Like those Howard Stern fans who irrationally insist on comparing him to Lenny Bruce, Letterman's staunchest boosters keep claiming he's "subversive," as if making apolitical, lightweight, vaguely racy jokes about certain people and institutions were the same as insightfully and constructively undermining them. When the institution being treated with aloof, postgraduate disdain is the American film industry, and the process is dragged out over four excruciating hours, you have to wonder why the perpetrator even bothered. Isn't it just a wee bit easy? And hasn't every televised Oscar contest in history done it already, either on purpose or by accident?
When the wide-eyed little boy makes his devastating observation at the end of the fairy tale "The Emperor's New Clothes," it's revealing because everyone else around the Emperor was pretending otherwise. If everybody in the kingdom already knew of the monarch's nudity, discussed it every day at the water cooler, and read about it in Entertainment Weekly, the fairy tale wouldn't have a punchline.
That's why Letterman's much-heralded star turn should have done something more than spell out that Hollywood is full of excessively self-involved rich folks, that most movies are entertainment and no more, and that there's no reason to treat either with undue solemnity. If there's anyone in this vast, diverse, colorful nation of ours who didn't already know that, I'd love to meet him.