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A Man of Many Faces

Impressionist Frank Caliendo brings his frenetic style of comedy back to the Orlando Improv this month.

When he’s actually being himself—and not a celebrity like John Madden,  Al Pacino or President George W. Bush—Frank Caliendo has a calm and laid-back persona, and it is easy to see that his reputation as one of the friendliest people in comedy is well earned.

But even a brief phone conversation with the master impressionist can zig-zag in many different directions, all of them hilarious. At a moment’s notice, Caliendo can start riffing in any number of familiar voices, from Charles Barkley to Morgan Freeman.

Caliendo’s love of characters started at a young age and spurred him to a career in show business that has included a five-year run on MADtv and his own show on TBS, Frank TV. He is also well known to sports fans for appearing on the Fox NFL pregame show for 11 seasons before moving to ESPN in 2015.

But Caliendo’s favorite creative outlet remains the stage and a bustling standup career that blends sports and pop culture. His latest tour returns to the Orlando Improv on July 17.

In between rapid-fire impressions, Orlando Family Magazine spoke to Caliendo about why he refuses to take sides in politics and his memorable meeting with President Donald Trump.

You’re a Midwest guy who now lives in Arizona, but you tour extensively on the East Coast. Do you feel like your comedy resonates here?
I think some of it is the sports culture, because that’s how so many people do know  about me. On the East Coast, people really do live and die by their sports teams. But also, the Midwest isn’t that far off from the East Coast style of humor. The East Coast is just a harsher version of the Midwest. When I first started doing comedy in the Midwest I learned to do it one way, and I found when I got to the East Coast you just do it slightly meaner, louder and faster. Whereas in California if you get too loud and fast they say, ‘Settle down.’ You can really feel that difference, and I just took to it. I’m also very sarcastic and there’s a lot of sarcasm on the East Coast.

Have you heard any feedback from the president about your impression of him?
I did a sketch with Trump years ago and he liked it. He was totally different off camera than he was on. He was like a used car salesman from the ’70s on TV, and off camera he was self-deprecating. That was the weirdest thing to me. It was like he was putting on a mask and becoming a character.

How did impressions start for you? Did you realize you had this talent at a young age?
It was from watching Saturday Night Live and In Living Color and watching those guys do characters more so than impressions. You know, Damon Wayans doing the bum, ‘My name is Anton.’ Or Jim Carrey saying, ‘Let me show you something.’ I always thought those kinds of characters were cool. I loved impressions, but usually people would just repeat lines from movies. I tried to find ways to make them characters, a lot more like Dana Carvey. Carvey is one of those guys who I think is super incredible. He doesn’t just do an impression, he turns it into a character who has its own point of view and is fun to watch.

So many people think they can do impressions even if they can’t. Do you get a lot of people coming up to you on the street and trying out their impressions?
Yeah, people will say, ‘I really love the way you do Yoda,’ and I’m thinking, ‘Anybody can do Yoda.’ But that’s the way they break the ice for them to do their voices for me.

It seems like you’re enjoying yourself more with certain impressions, like John Madden or Al Pacino or Oakland Raiders head coach Jon Gruden. Do you have favorites?
Yeah, some are just more fun. It’s funny because I know Gruden so well now. He’ll text me at 5 in the morning, which I think is lunchtime for him. He’ll say [in Jon Gruden’s voice], ‘I just did a commercial man, I had a blast. It was like being you man.’ And I’ll say, ‘Go to sleep, it’s 5 a.m.’ When you meet the people, it makes it more fun. When they haven’t seen the impression live, it’s kind of like a magic trick and they’re kind of amazed by it.

You had the long run on Fox Sports and ESPN. Did that just originate from your love for sports?
Yeah, that’s what I grew up with. I didn’t grow up around theater or anything  like that. My dad was a minor-league baseball player before I was born, and we just grew up playing football, basketball and baseball as kids in the driveway and backyard. I’ve had a lot of fun with that. It was what I knew, so it was the route I took. Nobody was doing sports comedy at the time, only Jimmy Kimmel on Fox. Now it’s everywhere and there are even comedy Twitter feeds. It’s become its own business.

You once appeared on the former Disney show Liv and Maddie. Was that with your children in mind?
Yeah, I did that because it was my daughter’s favorite show. She actually directed one scene in the episode and got to say ‘Action’. She was there and she has all the scripts to prove it.

You appeal to a wide range of people, and I’m sure you’ll see all ages in the audience during your show. Do you take pride in that?
Sure. I’m not for one specific group. Sometimes that hurts me, but I can only do what I think is funny. I’ve been in too many TV situations where they want you to do what they think is funny. But if I don’t find it funny and interesting, I don’t really want to do it.

Are you proof that nice guys can succeed in comedy?
You just think that because you don’t know me very well.

This article originally appeared in Orlando Family Magazine’s July 2019 issue.