With impressions ranging from Morgan Freeman to Charles Barkley, the comedian is headed to Dover Downs on Friday, Jan. 19.

Frank Caliendo is a master of disguise. Unlike Autobot leader Optimus Prime, it’s not Caliendo’s appearance that transforms. It’s his voice.

Whether it’s NBA Hall of Famer Charles Barkley, award-winning actor Morgan Freeman or President Donald Trump -- close your eyes while listening to Caliendo’s impressions and you’ll bet money (and lose) that you’re listening to the very person he’s imitating.

The veteran comedian’s resume includes a 10-year run on the “Fox NFL Sunday Pregame” show, as well as being on the cast of ESPN’s “Sunday NFL Countdown.”

Caliendo was a member of the sketch comedy show “MadTV” and also had his own series called “Frank TV.” This year he launched a new comic book podcast named “Comic Playground."

Caliendo will dish up belly laughs when he headlines Dover Downs Hotel & Casino on Friday, Jan. 18.

As an impressionist, how do you draw the line between flattery and insult?

I try to go with something that I really like about the person. Other people are going to have their interpretation of what that means or not. But I’ve found there’s a way you can do it. You can do something that you really like about the person. You find something you like as far as finding their ridiculousness funny, or something like that. Take, for example, how I do Donald Trump versus how Alec Baldwin does him. Alec Baldwin comes from a very angry/hatred of him kind of place. That really shows. You watch it and it seems miserable. I do it from this ridiculous, almost fantasy sort of Trump that doesn’t even make sense.

So you choose your impressions based on people you find unique?

The character I do of Charles Barkley is one where he thinks he’s better than everybody and smarter than everybody. Morgan Freeman is known as the wisest man in the universe. I talk about this in my act. When he plays God, you expect that. When God is going to show up in a movie, you expect it to be Morgan Freeman. I do a joke about when Morgan Freeman dies and says, “God, how do you think I did?” And God will look back at him (in Freeman’s voice) and say: “I thought you did pretty well.”

It’s unique you can do black voice impressions so well, since a lot of white guys don’t. Why do you think that is?

Would you say Jay Pharaoh does great white impressions?

Even regular blacks guy can do it. They don’t have to be high-profile like Jay.

It’s an interesting observation you’ve made. But I don’t know. I’m the whitest guy in the world [laughs]. That’s why it’s so funny, because if I walk into a hip-hop station and they say something to me, I’ll be like, “Does that mean hello?” That’s how awkward I can be. But for some reason, when I zero in on the people I do impressions of, it’s very specifically about the person.

So with Charles, he’s got a mix of a bunch of different things. He’s from the south. He lived in Philadelphia on the East Coast; and he probably just created his own way of speaking because he doesn’t care. He’s one of the smartest and greatest guys. When I say smart, he’s an incredible analyst. In terms of looking at culture, he’s brilliant. He’s got his own kind of thing.

There are some white guys who can do black impressions.

I know Dana Carvey has done a lot of black impressions. Even Darrell Hammond has done Jesse Jackson. He was really well-known for doing that. A lot of people have done Chris Rock. There’s a reality, and I say this about impressions with women too, that when people do impressions of women, they were always doing these old-school Katharine Hepburn [bits] and things like that.

Why? Because she was one of the few women who was allowed to get old in Hollywood. This speaks to diversity. How many huge-named black actors have there been, first of all? If you think about opportunity, they’re trying to rectify a lot of that right now and fix it. But you have fewer black people to choose from.

It used to be that Bill Cosby was the guy everyone looked up to. It might not have been contemporary African American life, but the attitude was at least there was a person on TV doing something good for black people. That’s a reality. And I think people are timid on doing black impressions sometimes. They don’t want to over generalize.

A lot of black people change the pitch of their voice to sound white. But many white people don’t do that when they’re trying to sound black.

When you hear a kid say “Yo, wassup,” I know what you’re saying; you can still tell it’s a white kid [laughs].

Exactly [laughs].

I just put out a podcast and it’s with Al Jackson and another friend of mine named Brian Love. It’s called “Al & Frank Try to Be Serious.” It’s not specifically about this impression stuff we’re talking about. But it definitely is a back-and-forth race conversation that’s really great, that’s kind of like what we’re doing now.

Some people would kind of feel super uncomfortable with it. But at the same time you’ll say, “That’s a great question. Let me think about this.” But I don’t know why others don’t do black voices. I’ve heard Bomani Jones [from ESPN] say when I was doing Stephen A. Smith’s voice, he thought I sounded like an older Jewish woman. I said (in Smith’s voice): “I’m incredulous to this entire situation!”

I just try to find people who I think enough people are going to know. I have, in all honesty, looked for diverse people to do at times, because I want to appeal to all people. I started out with very white audiences and I was like, “Why am I not appealing to everybody?” Then I realized I was in my own little culture zone. So I was trying to get out of that a little bit and do some things that make sense to me, are funny to me and will also be funny to a wider audience.

Everyone has tried to mimic voices at some point. But only a few go pro. How’d you stick with it?

It’s just something I tried and it worked on stage, so I just kept doing it. I used to do it a little bit when I was younger. I grew up watching “In Living Color” and “Saturday Night Live,” and “In Living Color” was way better to me than “SNL.” We used to recreate “In Living Color” sketches all the time. I would do all the Damon Wayans characters.

Are there any new voices you’re working on?

There’s always a lot of voices. Samuel L. Jackson is in the middle of it. I can do it sometimes, and sometimes I can’t. I’ve been working on every Marvel Avenger, because it’s just so big. But I’ve kind of gotten away from only doing the impression stuff, because it’s so limited and puts you in a box. I’m trying to talk about things like my son playing “Fortnite” and all that stuff on stage.