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

I think Michael Moore got booed for wearing a hat to the Oscars, which is really the truth.

That’s fair.

It’s disrespectful! But I don’t think everyone has to say something. I think, in a way, it will be refreshing if somebody chooses not to say something. Here’s the thing: I think people have different goals. Some people want to make themselves look good and that’s why they talk about things. Some people want to convince other people – and I don’t know how much you’re going to convince other people that your point of view is one they should share if there are 30 speeches denouncing the president in one awards show. So, I hope people are selective and that they don’t come in with a script they are planning to read if they win and that people just speak from the heart and spontaneously – and if that’s what want to speak about, great. But you’d just hate to see someone delivering a “speech.”

A speech that’s already been written as we speak and they are thinking, This is going to take him down.

Yeah, and you know that happens.

What prior hosts do you think did a great job and might serve as a kind of template

Well, some of them aren’t really templates. Because Billy Crystal was great, but I can’t do the stuff that he does. Ellen is probably the most similar to me, or at least to what I’m shooting for. She did a great job of mixing spontaneity with just a killer monologue. I think she kept it loose and stayed present through the whole show and really did a great job. So if there’s any template I look at, that’s the one.

I know you’re a Letterman person. I’ve been re-watching clips from his Oscars and they are very funny. I disagree that he “bombed.”

I’m glad you say that. I’m getting tired of defending him, but it’s his fault that people have this perception he bombed.

Because it was a 20-year-long joke for him that he bombed.

He’s the one who made that joke over and over again that he bombed! And at that time we didn’t have YouTube, so we couldn’t evaluate it for ourselves. You know, I think if you’re a Letterman fan, you enjoyed his job hosting the Oscars. And if you didn’t know much about him, maybe you didn’t. I obviously was and am a Letterman fan, so it was great when I saw it. I felt proud of him. This man I had a relationship with in the middle of the night had been introduced into the world.

He got Paul Newman to read a line from Cabin Boy. That alone is worth a reevaluation.

You couldn’t be more correct.

Re-watching, by the end I even laughed at the Uma-Oprah joke…

I know, right! And that’s pointed to as this low moment in Oscar history and it was anything but. Anyone who criticizes that, I challenged them to go just on YouTube and watch it.

It doesn’t get a huge laugh, but it’s classic Letterman in that he knows it bombed and he keeps saying it over and over again until you can’t help but laugh.

Right. He becomes fixated on those two words.

Do you look at hosting the Oscars as the no-win situation Like the Kobayashi Maru from Star Trek

First of all, don’t slip a little Star Trek thing by me like that and act like that’s not impressive.

I couldn’t help it.

I need to figure out how to spell that to look it up. Do I think of it as a no-win situation Only every day, all day, all the time. You have a thousand snipers aiming their laser target at your head when you host an awards show like this. It’s almost like you’re the next boyfriend or something: Everything you do is evaluated, usually negatively. I think I’ll be fortunate to get out of this unscathed. That’s the thing, even if the reviews are overwhelmingly positive like the Emmys, there are one or two you just go, “Well, what show was this guy watching and why does he hate me” And I, unfortunately, tend to fixate. If there’s an audience of 200 people laughing and one person has their arms folded, I zero in on the person who had their arms folded.

Captain Kirk changed the rules of the test to win, so you could try to do that.

Yeah, I thought Kobayashi was a wrestler, so you’ve really educated me on this.

Since Trump was elected, we’ve seen the late night shows ratings fluctuate lately. Political humor is doing really well. It’s an opportunistic time that right now you’re hosting the Oscars where you will be in front of a lot of people. Do you think about that

I think trying to guess what people might want to hear is the biggest mistake you can make as a comedian or a talk show host. You have to stick with what you think is funny and what your friends think is funny…

But that’s my point, new people might be introduced to what it is you do.

I mean, hopefully. I guess that’s the reason you do the Oscars – that it helps your nightly show and it makes some kind of impact and people think, “Oh, well, I’ll watch that guy.” It seems like that’s become a little bit a thing of the past. It seems like people are watching talk shows the same way they listen to music now. They will buy the single. And our version of watching a single is watching a bit every once in awhile from YouTube and not actually sitting through the whole show. But there are definitely fluctuations in what America is focused on. But they are fluctuations. It rarely lasts.

How much of your Oscar monologue is blank right now I know SNL has been leaving some cold opens unwritten until late in the week because there’s so much news.

Well, for the late night show, we don’t do much in the way of planning ahead. We are like a newspaper, in that there are a few things we will work on long lead, but for the most part we are dealing with the news of the day. But I will say, for this Oscar monologue, I’m definitely conscious of that and am definitely leaving a space open for whatever happens on Friday or Saturday or Sunday. If recent history proves anything, it’s that something will happen on Friday or Saturday or Sunday. God only knows what it might be.

I’ve been rewatching so many Oscar clips lately, I feel like you should look into getting Jack Nicholson and Burt Reynolds back there in the front row so they can just laugh the whole time.

You know it’s funny you say that because I had a conversation with Jack Nicholson about this about two months ago. [Laughs.] He’s very aware of the fact that if he’s sitting in the front section of the Oscars that the host is going to make fun of him. So I don’t think he wants to come any more.

Letterman’s Oscar impression of Nicholson was hitting a cab with a golf club.

[Laughs] Yeah, I know. Those were simpler times. Now our president is hitting taxi cabs with golf clubs.

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