Conan O'Brien on Becoming Late Night's 'Grand Old Man,' the Changing Face of Comedy, and Why He Still Hasn't Watched 'The Wire'

Note: This is Part 2 of our conversation with Conan O'Brien; Part 1 can be found here.

We got a chance to talk with Conan O'Brien at length last week about his new primetime special, Conan to Go (airing Dec. 18 on TBS), and while we had him, we couldn't resist getting his take on the current state of late night TV.

After all, he must have accumulated some wisdom by now: He started out succeeding David Letterman as the host of NBC's Late Night back in 1993, and now that Letterman's going off the air next May, O'Brien will suddenly be the veteran on the late night block. And that's not a role he's used to. At all.

"In the 22 years I've been in front of the camera, I would say for 18 of them, I was considered a young punk," he tells us with a laugh. But he's starting to get comfortable in the role of "grand old man," and he has plenty of thoughts on how the late night universe, and comedy in general, has shifted since he first came on the scene.

In fact, he had so much to say that we had to break our conversation into two parts. If you want to know more about Conan's new primetime special and what went into making his viral-video hits, click here. But for his deeper thoughts on the industry and his place in it, read on.

Letterman is leaving next year, and that will make you late night's elder statesman. Do you feel like you're now the old man on the block, dispensing wisdom?
I think overnight, the minute Dave goes off the air, I'm gonna suddenly morph into a Civil War veteran circa 1941: [in a raspy old man voice] "Yeah, I tell ya…" I think a lot of my segments are going to be me being very cranky, yelling at Rosario Dawson, "You don't understand! There used to be just three of us! Now it's all changed!" And just wandering off. Yeah, I'm looking forward to being the grand old man.

It's hilarious, because there's something about me, I don't know what it is… I have such a goofy attitude and approach to comedy, so in the 22 years I've been in front of the camera, I would say for 18 of them, I was considered a young punk. [Laughs.] Suddenly, Dave steps away, and it's "Tell us, oh wise one." I don't know why, but suddenly I have hair growing out of my ears and I'm lifting an X-wing fighter with my mind. But I'm looking forward to this phase, and I intend to make the most of it.

But late night TV has changed a lot since you started out, hasn't it? It seems like now everyone can carve out their own niche.
Yeah, it used to feel like stakes. In '93, I remember it was like a national question: "Who should have what show? Who is this guy replacing Dave?" And now what's fascinating to me is, with so many shows, you feel like you went from a sport where there was a wedge, a driver, and a putter, and now there are like 700 clubs you can use. And they're specialized.

And I think that about comedy in general. What's been very good for comedy is the variety. For many years, it was like, "These are the three comedy shows that are available on network television that are pretty good." And that was it. And now there are so many different approaches. You've got a Key & Peele coexisting with an Amy Schumer coexisting with Workaholics coexisting with South Park, but you've also got Colbert… every single approach.

And what I've liked about it is, in a way, it's become more freeing over time. You used to feel like you had to do a little bit of everything. And now you can focus more on the things that you really love to do. This whole idea of "you've got to construct this massive tent," it doesn't really exist anymore.

NEW YORK - APRIL 17: Late night talk show host Conan O'Brien chats with Dave when he visits the Late Show with David Letterman, Thursday May 17, 2012 on the CBS Television Network. (Photo by Jeffrey R. Staab/CBS via Getty Images)
NEW YORK - APRIL 17: Late night talk show host Conan O'Brien chats with Dave when he visits the Late Show with David Letterman, Thursday May 17, 2012 on the CBS Television Network. (Photo by Jeffrey R. Staab/CBS via Getty Images)

It also feels less cutthroat, less adversarial than it was back then. You've appeared on Letterman, you're friendly with Colbert… we're a long way from Arsenio saying he's gonna "kick Jay's ass."
Right. And also, we're getting into a world where no one even knows what "kicking someone's ass" means. In the 1960s and '70s and '80s and even into the '90s, you could kick someone's ass off television and they would disappear. And literally disappear. If you look at the history of these talk shows, people would challenge Johnny and they would be defeated, and then you'd see them three years later doing yard work. [Laughs.] "What happened to that guy?" "He sells prosthetic limbs door to door."

Now there's more of an appreciation of what different people are trying to do. It's become so fractured: people watching out of sync, there's online hits… people are less obsessed with the spectacle of it all and more just appreciating what different people are trying to do. They like this, they like that, they like what this person does, they like the other thing that the other person does. So I'm OK with that. As I age, my testosterone level has been plummeting. So I'm much more accepting. Pretty much, I'm gender-neutral now. What I'm saying is, I'm a sexless man who's very happy with all the other comedians now. I'm very different from how I used to be. I couldn't grow a beard now if I tried.

People have complained about late night's lack of diversity. Are there any comedians who aren't white males that you'd particularly like to see get a opportunity?
It's funny, because I feel like anybody… could? It doesn't even have to be a late night show. Amy Schumer is hilarious, but then I think there's no, "Oh, she's being banned from doing late night." She can do her own thing. I think everyone can find their own focal length that matches them.

I think there used to be a thing where, "Oh, it's a boy's club, or it's this or it's that." But nobody now who has any sense or knows anything about comedy… it's just, there's Amy Schumer, there's Tina Fey and Amy Poehler, there are so many absolutely hysterical women. I mean, Ellen's show could be on at 11 at night, it could be on at 12, it could be on in the daytime. I don't even make the distinction myself anymore. People who make me laugh make me laugh.

We've had Key and Peele on a lot, and they have some of the smartest sketch comedy I think anybody's doing, period. Absolutely brilliant. They have such brilliant observations, and they're so versatile. I absolutely love those guys. So I think yeah, they could have a late night show, but why? [Laughs.] Just do what you're doing, and we can see it at any time of night. I feel the same thing about Mindy Kaling, who we just had on the other night, who is hilarious and I love her. If she wanted a late night show, I'd say, "Great! Do it! But why? You're getting to be funny the way you're funny right now."

Now technology has, and it's just an accident of technology, but the technological changes of the last 15 years have made it possible for just about everybody to express themselves. For good and ill. Go on the Internet, and you'll see a lot of… the ill. I'm just talking about pornography. You know, it's badly lit.

You're obviously a big TV fan; you've had the casts of The Walking Dead and Sons of Anarchy on your show. What was your favorite TV show this past year?
The one I'm not hearing enough about that I thoroughly enjoyed was Fargo. I don't hear people raving about it as much as they should. I thought that was a fantastic show. I am a big Coen brothers fan, and Fargo's one of my favorite movies, so when I heard there was going to be a TV show, I was very skeptical. And I loved that show. I thought it was funny, but also bone-chilling… I mean, I savored every episode.

I've long been a fan of Colin Hanks, and I thought he was fantastic in that role. It's a flawed character who breaks your heart every episode, but you keep coming back to see him get it right. Allison Tolman… I hope that what she did is recognized. I thought she was absolutely fantastic. There are plenty of other shows I really liked, but they've been lauded a lot, and I feel like more people should talk more about Fargo.

And do you have any TV-related New Year's resolutions for 2015? Anything you're planning to binge-watch?
I still have not seen The Wire. And it's one of those things now where… I feel like one of the early Christians, I have to go underground in Rome and pretend. And then there's some defiant part of me where everyone says, "No, no, it's all about The Wire… until you see The Wire, you can't truly understand…" I've had the Wire box set loaded, and it started to play, and I jumped out a window. Sometimes I think I'm the last person on earth who hasn't seen The Wire.

I'm supposed to have seen The Wire. If you break down everything about me, I'm supposed to have seen The Wire and really love The Wire and I should still be talking about The Wire. But I haven't seen The Wire. It's like being a film critic who hasn't seen Citizen Kane, and you're afraid of being found out someday.

This year, I'm going to watch The Wire. And I'm saying it like, "Finally, I'm going to get that colonoscopy." [Laughs.] This doesn't sound flattering. My doctor said that now, at my age, it's time to see The Wire, if I really care about my children and my future. And I'll drink whatever I have to drink the night before.

For Part 1 of our conversation with Conan O'Brien, click here.

Conan to Go airs Thursday, Dec. 18 at 10 p.m. on TBS; Conan airs weeknights at 11 p.m. on TBS.