'I can poke fun at all sides': Harris and Trump impressionists prep for debate night

President George W. Bush won Florida in 2000 by 537 votes.

Setting aside the U.S. Supreme Court and the Palm Beach County butterfly ballots — in a race that close, any number of factors could have persuaded just enough voters to go one way or another, and ultimately determine the presidency.

So there is an argument that Darrell Hammond’s brutal impression of Vice President Al Gore on Saturday Night Live, portraying him as stiff and unlikeable after the 2000 debates, could have swayed the outcome.

In recent decades, comedians like Tina Fey have become merged in the minds of many with the politicians they roasted, like then-vice presidential nominee Sarah Palin in 2008.

And beyond SNL, Key and Peele's “anger translator” bit helped define President Barack Obama’s aloof coolness.

These days, a lot of the most incisive political comedy — and the best impressions — aren’t happening on TV. They’re happening on TikTok and Instagram.

So how much could impressions and satire shift voters, if at all? And how do the comedians think about their role?

Ahead of Tuesday night's debate between former President Trump and Vice President Harris, All Things Considered host Scott Detrow put these questions to two of the most prominent political impressionists out there — Matt Friend, who’s become famous for his impression of Trump, and Allison Reese, who’s gone viral for her portrayal of Harris.

These interviews have been lightly edited for length and clarity.

Matt Friend — aka Donald Trump

Scott Detrow: It's very unfunny to ask deep questions about comedy, but here we are. Why do you think people are so drawn to impressions; political impressions, especially?

Matt Friend: You know, I think especially in America, there's such a rich history of it and a great tradition of it. And I think it kind of shows truth to power in a way that maybe other forms of comedy just don't. We're seeing alternate representations of people that we might like or people that we might not like. And obviously, with SNL amplifying it in the ‘70s, I think people obviously went crazy when Chevy Chase was doing it. And then even before that, like there was Rich Little and then Vaughn Meader is a famous one and he did a JFK impression and he looked exactly like JFK and that was his whole thing.

Detrow: Is it fair to say that Trump haters and people who like Trump kind of like your stuff just as much? Or do you think your mentions are one sided or another?

Friend: I think that everybody's commenting on it. And now an interesting thing is happening where if I do an impression of him, there are some people that say like, “You're too left” or, “You're too woke” — and all I'm doing is repeating exactly what he's saying. And they'd say, “This is offensive, this portrayal.” I'm like, no, he actually just called this person a dog. Or he actually just said that Kamala Harris decided to become Black six years ago.

But ideally I can make the whole country laugh. I mean, I like to think that I can poke fun at all sides.

Detrow: So we're talking right before the debates, and I feel like historically the debates are quite the opportunity for impressionists. How are you thinking about it for what you do? And are there any classic debate related things that were some of your favorites?

Friend: You know, it's so interesting because I'm just so consumed with creating every day. So like, this is not a different moment, just that there's more eyeballs on it. You know, more people are paying attention in this specific political moment. But I'm just going to be creating videos and comedy and content like I always do. But obviously there's a lot of opportunity here. So we're going to see how this debate goes.

I mean, we'll see if there's another Trump circling moment, like when he was circling Hillary, as if it was Jaws — I think that was a funny SNL parody, they put the Jaws music on there.

Whether it was Bush, I think he's the one who checked his watch. Or obviously the, “You’re no Jack Kennedy.” There's so many legendary quips and things to point to.

Allison Reese — aka Kamala Harris

Detrow: How much do you focus on accuracy, or the vibe of just going for a funny situation?

Allison Reese: I would hope that it's an even split. I want the accuracy, of course, but I find impressions are so fun when you add your own flavor to it. And I add a lot of my own flavor, a lot of my own sassiness and my own quirks to it. A lot of the stuff I say is stuff I'm sure she would never say.

Detrow: There's been moments where a high profile impression of a political figure almost overtakes them and clearly influenced the way people think about them. And on one hand, you have Donald Trump, who people have been doing impressions of for, like, 40 years at this point. But one of the interesting things about Harris is even though she's been vice president, there's a lot of Americans who are kind of still forming an opinion of her. How do you think about that when you're putting your material together?

Reese: I think about it a lot, to be honest. I mean, I know that comedy has a really powerful influence on folks and tends to have a hold and is a way that people can retain information better, in fact.

So it is not lost on me, the gravity of me doing an impression of her and how it will be in people's minds and voters' minds. I don't know that anybody who is going to make a decision based off of an impression is, you know, any sort of a thing to look at. But it's not lost on me that that is important. And I've taken a lot into consideration with that. And it's just so funny because satire really wants to put a mirror up to our society and culture.

Detrow: Do you ever think about whether Vice President Harris has seen your videos?

Reese: I do think about that all the time. I used to have nightmares where she would be there. I'd be like, “Oh, my God, it's Kamala Harris!” And she would see me and go, “Oh God, it's you.” And then like she’d be like “Come on, Doug, let's go. It's that girl.”

But I hope she's seen it, and I know that folks on her staff have seen it and they really like it. So I'm like, OK, that probably is good. Also, being an artist, you want to have that space a bit when you're impersonating somebody just to keep it pure as well as, like, honest and respectful.