David Letterman: First (Last) Modern Oscar Host

David Letterman, of course, was an irreverent late night talk show host on NBC, not a movie star, and that’s why his most memorable turn in a movie basically felt like an irreverent late night sketch on NBC. It was “Cabin Boy” and the irascible Letterman turned up for a walk off cameo as a man who wants to sell a monkey to Chris Elliott, Letterman's old protégé. The monkey, as it turns out, is merely a sock puppet. It’s that chancy kind of comedy that’s essentially attempting to be funny by rubbing your nose in how not funny it is. Succeed, and it’s cultish, maybe. Fail, and crickets. And a year later when David Letterman walked onto the stage at the Shrine Auditorium to host the 67th Academy Awards, he may as well have been wearing that sock puppet.

Oscar hosting is a tale told of woe and cataclysm. Letterman’s lone stint might have been the most cataclysmic of ‘em all. It was so legendarily terrible that Letterman himself would often make it the butt of jokes. And that, of course, is classic Letterman. He’s a man, it is well known, plagued by self-doubt and insecurity, and comically he thrived on it, particularly in moments when his worst jokes bombed. If a joke was awful, he'd return to it again and again, driving home its awfulness so insistently that you couldn't help but laugh. In fact, those were the moments I often laughed hardest. If he’d failed at the “Would you like to buy a monkey?” joke on NBC, he would have issued that same query to poor Paul at least 17 more times before show’s end.

Frankly, I can’t imagine how anyone thought David Letterman hosting the Oscars would not amount to exactly what it turned into. “(T)he ceremony went to the far side of blatantly meretricious blandness and made no pretense about its safe and self-protective conservatism,” wrote a most Brody-esque Richard Brody in the wake of the 2013 Academy Awards. “The shticky suffusions of show-biz tradition were replaced by a rigidly plasticized shell of industrial defensiveness that wore its bank-vault-like mentality up front.” That stuffiness, that resistance to (fear of) spontaneity, is precisely what Dave played against. He took “the rigidly plasticized shell” and conked them all over the head with it; because he’s not just flippant, he’s an adversarial wiseass.

Watching him in 1986 try and deliver a fruit basket to the headquarters of GE who had just bought NBC was incredible. He wore a Late Show letter jacket like he was a high school student on a class field trip. It was like the preamble for every GE joke unfurled on “30 Rock.” If anyone was going to be master of ceremonies at Hollywood's big party and not care what Hollywood thought it was David Letterman. Introducing Uma to Oprah, and Oprah to Uma, was the equivalent of that fruit basket, making the introduction ultra-awkward. He wasn’t there to cater to them, he was there to cater to us. No, no, no. He was there to cater to himself. That infamous Letterman “hee-hee” conveys, as it always does, self-amusement.



“If you were a guest who was a normal human being, you were fine — he’d be curious and ask thoughtful questions. But if you had airs? There was nothing more fun to watch than Letterman effortlessly deflate people with inflated senses of worth,” wrote Daniel Kellison for Grantland in recalling the years he spent working for Letterman, and that's exactly how his former boss hosted the Academy Awards. Everyone mocks the Oscars incessantly for being a bunch of self-important people getting dressed up to lavish each other with awards. Letterman treated it exactly as that and gleefully forced them all through his Worldwide Pants-ish wringer. Had he hosted like that in the present day, he would not have been a dud; he would have been a smart-aleck savior.