ABC7 entertainment reporter George Pennacchio sat down with O'Brien, who is fresh off his stint playing a therapist in the Oscar-nominated film, "If I Had Legs I'd Kick You."
But what if Conan had starred in other films nominated this year? George was ready for that.
Check out the hilarious results in the video above as O'Brien's mug is plastered on the faces of Hollywood's A-list.
Meanwhile, here is some of George's interview with O'Brien as he gets readu to host the Academy Awards for the second time.
"You said yes so early to coming back. I'm wondering if that built up the stress or made it more fun?"
"That's a good question. I said yes because I had such a good time last year. I thought, oh, I'd like a little more of that. That tasted delicious. And then I wouldn't say it increased the stress, but it certainly got me thinking about it earlier. And maybe that wasn't always my wife's favorite thing. 'Cause you know, well before Christmas, I was saying, what about this? What about that? Hey, what about this? And she was saying enough already, okay. So I had to learn to keep it to myself."
"So her Christmas gift was your silence."
"For one day. She got my silence for one day."
"Do you think it will be easier this year because you've done it before or are you setting new standards for yourself?"
"I wouldn't say it's going to be easier because it's always the same and comedy is tricky and it's not a science and so no, nothing about it has felt easier. Some of the conditions are not as difficult as last year. We had the fires last year, I was living out of a hotel. We were displaced, things were very chaotic."
"Do you know that you have a monologue that people will say is special?"
"We have a lot of fun stuff planned... and then some things that you loved before maybe come down in importance. And then, some things that you thought, yeah, I'm not so sure about that idea. You get it on its feet and it rises. So, we'll find out. We are working on this thing up until the last minute. And then throughout the show, it's still in play because... Something could happen, things could go right, they could go left, they could sideways, and you gotta be ready."
"Now that you are a bona fide movie star, thanks to "If I Had Legs I'd Kick You," will you be a target of your own monologue?"
"It's possible, you know, I don't like to make fun of myself because I think I'm perfect."
"Has being in that movie make you think, 'I want to be in more films'?"
"Getting a chance to act opposite Rose Byrne... and be directed by Mary Bronstein; if you think about a jackpot, it was all three cherries in a row. It was just perfect and I don't know that that's going to come up again. I really love doing comedy, I love what I do, and I have way too much respect for real actors, but if the perfect thing came along, you never know."
"Here's what I like most about talking to you. I didn't really know you last year. I came in here, you were the friendliest man. You gave this great interview. You are the same person that is here to have a good time and entertain us. And I think when your mindset is like that, it's better for all of us who are tuning in."
"I do think that people are very stressed out there. And I do want to be, as host, you need to be aware of what's happening in the world. We're not in a bubble. We all know that these are stressful times for everybody. But you also want to entertain people and give them a feeling of connectivity. Because it's a rare chance to get everybody together and say, maybe "Sinners" is your favorite movie, or maybe it's "One Battle After Another," or maybe its "Bugonia," or maybe it's "Hamnet," whatever, but we can all agree these are great movies, let's get together and celebrate all the hard work."