Jimmy Kimmel On Hosting The Oscars And Knowing It’s The Kobayashi Maru

Jimmy Kimmel does not want to hear about how David Letterman bombed as the host of the Oscars in 1995. Kimmel, who will host the 89th Academy Awards this Sunday, is a strident defender of Letterman’s show. (For the record, so am I, but even bringing this up sparked ire in Kimmel’s demeanor.)

The problem with hosting the Oscars is that it really is the Kobayashi Maru: the unwinnable test Starfleet officers are put through that we see at the beginning of Star Trek II: The Wrath of Khan. What Kimmel has in his favor is that he’s fully aware that he’s about to take the Kobayashi Maru. He’s fully aware he can’t completely win. So, maybe in that respect, he’s already won.

Ahead, Kimmel takes us through some of his preparation for the Oscars (for example, he’s leaving part of his monologue empty in preparation for what crazy Trump-related news story that we all know is coming will happen later this week), his template for the perfect Oscar host, why he can’t get Jack Nicholson to attend, and his hope for all the sure-to-happen Trump-related acceptance speeches.

Kimmel: What are people’s reactions when you say, “I’m Mike from Uproxx”?

When I worked at Huffington Post people assumed I didn’t have a salary, even though I did. So this is better.

Sure. But it sounds vaguely dirty, you know? There’s something about it.

Christian Bale asked if it was a drug site.

Oh, that’s funny. Didn’t you guys put together a big retrospective of my relationship with Matt Damon?

We did.

I enjoyed that.

Political Oscar speeches used to be fairly rare. I remember Michael Moore got booed. But this year, do you think there’s more pressure for winners to say something?