By Eliana Dockterman
Updated: December 16, 2015 5:25 PM ET

Larry Wilmore said Wednesday that he can talk more freely about race than previous headliners of the White House Correspondents’ Dinner have when he hosts it next year — the last one of Barack Obama’s presidency.

“Because maybe I have unsaid permission, I think I can talk about race in a way where maybe somebody might not have,” The Nightly Show host told TIME in the his first interview since the announcement was made. “I think I’ll have some fun with that.”

Wilmore said he’s particularly excited to take on the challenge for Obama’s last year. “It’s kind of an end of this particular era in our history, which to me has been very significant. The thing that will outlast any Obama legacy of legislative achievement will be the mere fact of his presidency,” he said looking ahead to the April event. “It’s not an issue to future generations and young generations that a black man can lead a country. When I was a kid, a black man couldn’t even be the quarterback of a football team. That alone is so significant. And that’s why it’s so meaningful to me that I get to do it in this last year. It has a sort of resonance for me.”

And Wilmore added that he feels a personal connection Obama: “I’m the same age as the President too, so it’s sort of interesting. Bringing that perspective is going to be fun for me. It’s like, ‘I was a young black man at the same time as you were, Mr. President. And look where you went, and look where I went!'”

“I can have that perspective because we grew up in the same world,” Wilmore said. “We were both born at the time when there were separate water faucets for “white” and “colored.” The Civil Rights Act hadn’t been signed yet. That’s the world we were both born into — me in California and him in Kenya. It’s the exact same world.

“Oh no!” he said with a laugh. “I’m giving away all my jokes!”

See more highlights from TIME’s interview with Wilmore below.

TIME: How will this being Obama’s last Correspondents’ Dinner affect your routine?

Wilmore: There’s not enough time to sick the IRS on me if I’m completely out of line.

Who do you think it will be the hardest to write jokes about?

It’s always hardest to write jokes about the President. Always. Especially this particular President because Obama has that cool factor and he’s really funny himself. So you have to follow this cool guy who’s really funny and is everybody’s boss in the room. And I can guarantee you he will be pulling out all the stops because this is his last one for him.

Who do you think the softest target in the room is?

That’s a tough one because we know how fast the political cycle goes. My feeling is Trump is still going to be around in some way, so I think I’m going to have the opportunity to talk about him a bit and whoever will be at the top of that ticket at that time because we’ll know the nominee at that time. We should know the democratic side too, and we’re in such suspense right now about who the democratic front runner is.

Are there any lines you can’t cross?

Not right now. I never do that at the beginning of the process. I’ll do that as I get closer and get a sense of what’s happening at the moment. Something can happen the day before that can prevent you from doing jokes on a certain topic. But when you’re first thinking of it, you want to go as far as you possibly can and then pull back if you have to. So the first round of jokes that no one sees will be the most hardcore. Like, the ones that maybe eventually leak on Facebook.

Who have been the best Correspondents’ Dinner hosts in your opinion?

I’ll tell you, Seth Meyers did a great job a few years ago. I mean, he was on fire. You can look at it now and those jokes are still so funny. I thought Cecily [Strong] did a good job last year. She had some pretty poignant jokes. The room wasn’t quite there, but I think when you look at it, it played better on TV because she got a little dangerous on some of it, and I give her credit for that.

And of course, Colbert: the thing he did is legendary. A lot of people didn’t know his character at that time, he was just kind of starting it. I think he’d done his show for maybe six months at that point. People didn’t know if it was a joke or what was going on. Oh my God, that was one of the most uncomfortable ones. That one stands as probably the most epic.

He came close to really ticking people off. Then you look at someone like Leno, and he’s a little more jovial. Where would you like to fall on that spectrum?

My style on this show is we keep it 100. We tried to tell the unvarnished truth as best as possible. I’m not going to be doing performance art like Colbert. So I guess it will be closer to the Seth Meyers-style of skewering people in the room.

You’ve gone after Trump for using racism in his campaign. Would having him in the room when you tell that joke change the way that you tell it?

Oh, it won’t. Normally it might. But in this situation, it’s probably a bonus because there’s something interesting about the combination of something being very uncomfortable and funny at the same time. I think this is one of those situations where people expect to get skewered, so it’s not a surprise. And you get to see their reaction, so it’s kind of nice if someone’s in a room. And it’s all in fun.

Some people think the joke Obama made last year about Trump at the dinner inadvertently fueled Trump’s decision to run for President. Are you concerned about any real-world fallout from your jokes?

Well he’s already running, so I don’t have to worry about that. I guess I shouldn’t do any jokes about him winning. But no I haven’t thought that far ahead.

You did an interview with TIME when you first started The Nightly Show where you talked about how you wanted to be a voice for the underdog. A lot of people have criticized the Correspondents’ Dinner for being the ultimate top-dog event. So why do it?

I know exactly the type of thing that you’re referring to, but the White House Correspondents’ Dinner is a charity event. It’s done for scholarships for journalism students. It’s all for a good cause. For someone like me, it’s a once-in-a-lifetime chance to be the court jester for the king. And that opportunity is impossible to pass up. It’s that phrase, “I serve at the pleasure of the President.” From a citizen’s point of view and a comic’s point of view, I could never turn something like this down because you’re doing something for the President, and it really wouldn’t matter what the President is.

What do you think you can bring to a room of the most powerful people in America as that voice of the underdog?

You’re absolutely right. It’s this weird combination of Hollywood and Washington. So I’m definitely hoping to bring that underdog feel to it. I’m always trying to think from that perspective.

Last question: Who do you think won the GOP debate last night?

The real winner of the night was Lindsey Graham. He kept it 100. But the winner of the debate is still Donald Trump because nobody took him down. The only thing that will last out of that is the fact that he’s still on top. Unless you really take him down, he’s going to win. That’s pretty much how it goes—Larry says somewhat sadly. But we’re going to have some fun talking about it tonight on the show.

Write to Eliana Dockterman at eliana.dockterman@time.com.

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