Frank Caliendo: A Career in Comedy

March 11, 2016

Frank Caliendo’s career includes plenty of tomfoolery, or should we say Frankfoolery? You’ve probably seen the American comedian and actor on any number of shows, especially if you’re a sports fan; in addition to appearances on MADtv, The Bob and Tom Show, Comedy Central Presents and sitcoms Hot in Cleveland and Sullivan and Sons, Caliendo was a regular on Fox’s NFL Sunday for 11 years. And we haven’t even started listing his standup appearances on late night shows hosted by the likes of David Letterman, Conan O’Brien and Craig Kilborn.

Caliendo has the innate ability to nail impressions of everyone from sports analyst John Madden and singer James Brown to President Bill Clinton and the cast of Seinfeld. It’s a specialty he started developing while in college in the early ‘90s, when he began doing standup. The first place he performed comedy was a dance club where management had forgotten to tell patrons there was going to be a talent show instead of dancing. That night may not have gone over well, but it was still notable as the beginning of Caliendo’s upward climb.

Express: Frank, I’ve not heard a lot about your early years, so I wanted to ask what first inspired you to get into comedy?

Frank Caliendo: As a kid, I watched a lot of television, mostly sitcoms. I especially loved Mork and Mindy. As I found out more about Robin Williams, and later Jonathan Winters, I wanted to learn more and more about comedy. As I got older, I started to love sketch comedy: Saturday Night Live and In Living Color, among others.

Express: Did you jump right into standup or did you try something else first?

Caliendo: I actually ended up getting a degree in broadcasting, mostly because of that love for television. I didn’t know what I was going to do in TV, but I figured I could do something and, from there, I just kind of got lucky.

I started going up on stage in my hometown of Milwaukee, and with all of the impressions, I just started to take off.

Express: When did you hit that point where you could say to yourself ‘I think I can make a go of this as a career’?

Caliendo: I really don’t know if there was a single moment; it seemed to happen over the course of a year or so. I had my degree, but I didn’t really want to do anything structured, so I just went on the road and started doing comedy. I guess I realized it could become a career somewhere around the beginning of my second year doing comedy. I got on the college circuit, and I was very close in age to the students, so it worked really well and was very lucrative.

Express: And you’ve had so many high-profile gigs since then, on everything from big radio shows to late-night talk shows to the major sports networks. What are your top three big moments so far, and why?

Caliendo: That’s a tough question! I’d have to say my first Letterman appearance was pretty big because I’d always been told Dave wouldn’t have people on who did anything besides a straight monologue. I’d also have to say the segment I did with Mike and Mike where I read a Lebron James letter as Morgan Freeman, because of how big it went virally. And, finally, I’d have to say the 30 for 30 mockumentary I did for ESPN a couple years back about Richard Sherman; that was something else that kind of took on a life of its own. I couldn’t believe how big it was.

Express: Do you have a certain type of performance that you enjoy more than others?

For instance, would you rather do standup or acting or…?

Caliendo: I like them all. For me, the variation keeps it fun. Each platform works different muscles and they are very different from each other. I guess I would pick standup as the one because I can make a living off of it. The others aren’t as consistent and you’re really depending on lots of other people.

Express: I know you’re not doing that particular gig anymore, but what kind of impact did your appearances on Fox’s NFL Sunday have on your career? Would you have taken that gig again, knowing what you know now?

Caliendo: That was huge. It really changed my life. I was associated with the NFL and Hall of Famers and it brought me to a different level. I absolutely would have done it again. In the same way, my move to ESPN gave me a different type of exposure, a much younger and diverse audience, which is something I always wanted. I do think the sports stuff has pigeonholed me quite a bit, but the good it has done for me has far outweighed the bad.

Express: Let’s talk for a minute about a completely different type of gig: road shows. I noticed you have a pretty busy schedule of those at the moment. What do you like best and worst about them?

Caliendo: The best part is probably that I’m always in a different venue, with different people. The least — well, I used to really like the opportunities to go to so many different cities, but now that I have kids in school, the travel has become much less fun and I’m always thinking about getting back to being with my family.

Express: Can you tell us a little about your newest routine and which characters you’re bringing along to your current shows?

Caliendo: There’s a mix of everything. There’s some older stuff that I have to do — Madden, Pacino and all — but there’s definitely a lot of new stuff. And Donald Trump has really made it easy. Some nights I do the Trump impression for 20 minutes and then keep going back to it. It’s a Trumpacopia.

Express: Well, you should be able to keep the Trump going for at least another eight or nine months! Do you plan to stay on the road all year?

Caliendo: Well, as I wind down [from the road shows] a little more in the spring, I’ll be working on my acting more and more; I’d like to do some real acting, just some smaller parts. As I’m learning about that craft, I find it more and more interesting. And I’ll also be working on doing more Internet sketch types of things. I kind of just work at stuff and go with the flow!

Frank Caliendo will be appearing at Leelanau Sands Casino on Saturday, Mar. 19; tickets are on sale now at ticketmaster.com or (800) 745-3000. For more information, visit leelanausandscasino.com or call the box office at (231) 534-8150.