Comedian Frank Caliendo on how he created 30 for 30 “mockumentary” featuring ESPN, NFL personalities

How did Frank Caliendo make the physical transformations into his characters? Said Caliendo: “For makeup, there was a system. We built things on top of each other and took them off depending on the character. For example: With [ESPN “Monday Night Football” analyst] Jon Gruden, we glued on a nose and a chin piece (to lengthen my face a little) and put the Gruden wig on. That same makeup was then used for [ESPN NFL analyst] Mel Kiper – just change the wig, darken the eyebrows, and put the glasses on. We then took off the nose and added some tooth white for [ESPN NFL Insider] Adam Schefter and made some small changes to the shadows and such on my face. To go to [San Francisco 49ers head coach] Jim Harbaugh, we just put a hat on and changed some shading. Then when I went to [for former President George W.] Bush, we just added the Bush wig. For [former President Bill] Clinton, we changed wigs and added a nose piece. We did something very similar with Boomer [ESPN commentator Chris Berman] and [New England Patriots head coach] Bill Belichick, and eventually Jaws [ESPN NFL analyst Ron Jaworski]. The others were mostly shading and wigs (adding a mustache for ESPN NFL analyst Mike Ditka and Kansas City Chiefs head coach Andy Reid).

One of the highlights of ESPN’s special four-hour Super Bowl Sunday NFL Countdown last weekend was comedian Frank Caliendo’s 30 for 30-inspired “mockumentary” about how Seattle Seahawks cornerback Richard Sherman became president.

The nearly four-minute piece (see digital version of the video above) – which was widely praised on social media and elsewhere – featured Caliendo doing 11 different impressions. From ESPN commentators Chris Berman, Ron Jaworski and Mike Ditka to NFL coaches Jim Harbaugh, Andy Reid and Bill Belichick, and former presidents George W. Bush and Bill Clinton, the segment demonstrated the impressive talents of Caliendo.

Having just completed his second season as a Countdown contributor, Caliendo discusses his 30 for 30 with Front Row.

How did you come up with the idea?
It came in phases. I knew that I wanted to do a documentary-type of segment – something with lots of talking heads – new impressions, mixed with some older ones. I wanted it to have a very serious feel with real footage, and I wanted to use the characters to tell the story. A friend, Jeff Rothpan, suggested a sketch about Richard Sherman for president. I thought it was interesting, but too one dimensional. However, I thought that premise could be a beat in the sketch. It would seem just crazy enough and be a good punchline. Once I knew that was the payoff at the end, I started thinking of a story arc. I thought it could be a good social commentary too – the fact that because of social media, you can become famous almost overnight and end up with all kinds of opportunities from that instant fame. A 30 for 30 seemed to be a natural fit.

How long did it take you to write and shoot the piece?
I had some ideas lingering for a while. I knew I wanted to do a Chris Berman, Bill Belichick, and Ron Jaworski (I had been saving these characters). The main writing took 2-3 days, then lots of tinkering for a week or so. That’s usually the process. I also get help on punching things up from a group of a few people after I get the main beats of the sketch down. Shoot time only took two days, but with lots of crazy fast makeup changes. I had Berman down pretty well, but the other two impressions were not that good going into the shoot. For Jaws, I was able to key in on a couple of words during the shoot and it just started to happen. It got better and better on every take and suddenly it felt great. Belichick was like cheating. I knew I could do the facial expressions, so I just mumbled (which I had planned from the start). I always knew I wanted to do subtitles with Belichick. For some reason, I knew it would work. Lots of things just happened on the set, too. I added the dog, which I originally had not planned. We cut the sleeves off the hoodie and cut holes in the removed sleeve and put it on the dog.

What are your favorite impressions in the piece and why?
That’s like trying to pick a favorite son or daughter. It’s really hard to pick. Jaws was a ton of fun. He’s just so upbeat and fun to watch on TV. Kiper, Gruden, Schefter and Ditka were a blast, but people had seen them before. What I’m trying to do at ESPN is really add some new stuff to the repertoire. Berman is so iconic. I really wanted to do him. I knew I could do that impression in a fun way.

“I think I did every impression I wanted to do,” Caliendo said. “I had a list of a few others like [Dallas Cowboys owner] Jerry Jones, [ESPN host] Bob Ley, [new Washington Redskins head coach] Jay Gruden and [former NFL analyst] John Madden. I thought pretty hard about whether I wanted to do Madden or not, but in the end, I wanted to do something great without that impression being involved. I just thought people would have focused on it.”

What reaction have you received to the piece?
It’s been crazy good. I usually hope for about 60 percent positive. Doing comedy on a sports platform is always tough. It’s like a comedian being an opening act for a superstar musician. People are looking forward to a certain type of entertainment, and you have to break down that barrier.

What’s the next big ESPN or NFL impersonation you are working on?
I’m really not sure yet. I think [ESPN College GameDay analyst] Lee Corso would be a blast. Mark Schlereth would be fun. Maybe Tony Kornheiser.

Now that NFL season is over, what’s next for you?
I’ll be on the road doing standup (www.frankcaliendo.com/schedule), mostly working on new material, and performing for lots of corporations and conventions. I also have a podcast called “The Podfathers” with a couple friends, John Holmberg (who added some great ideas to the 30 for 30 segment) and Chuck Powell.