On Halloween night, the Milwaukee Bucks had their home opener against the Sixers. It was a rare sold-out crowd at the Bradley Center, and the crowd had an energy that was both hopeful and nervous. This was largely a new Bucks team. In the off-season, there had been a change in ownership; a new coach, Jason Kidd; and the acquisition of a then-healthy rookie, Jabari Parker.
On the sidelines, comedian and Wisconsin native Frank Caliendo shared the fans' hopeful and nervous energy. Except he was less focused on the game and more concerned about how his set was going to go. Caliendo was the night's half-time entertainment.
"I had no idea how doing standup was going to go over at an NBA game. I figured most people were going to ignore me, go to the bathroom or get a beer," says Caliendo in a phone interview with Isthmus.
Caliendo's half-time set was a success, which is more than one can say about the Bucks' last season.
"People were into the half-time comedy. I was pleasantly surprised," says CCaliendo. "It was really fun; I got to goof around with [Bucks mascot] Bango, and they let me fire the T-shirt cannon."
When asked why he decided to take the half-time gig, Caliendo's response is simple.
"I had never done something like that before. It was an opportunity to try something new," he says.
That desire to try something new has driven Caliendo throughout his career. His ability to combine spot-on celebrity impressions with heartfelt humor made him a star on MADtv and the Fox NFL Sunday pre-game show. Now, Caliendo is appearing on ESPN and touring the country, with a stop at the Overture Center's Capitol Theater on Jan. 15.
As a student at Waukesha South High School, few would have suspected Caliendo would someday make a career out of being on stage.
"You wouldn't have really noticed me my freshman year of high school. I kind of blended in. I got decent grades but wasn't always noticed for it. I played a lot of sports, but I wasn't exactly a jock," he says.
It was during high school that Caliendo would get his first experience mixing sports and comedy.
"I was the catcher for our baseball team, but I'd usually spend most of my time out there cracking jokes. I'd try to distract the batters or make the umpire laugh," says Caliendo. "In class, I also started doing impressions of my teachers. I guess I've always enjoyed doing impressions."
After making classmates and family members laugh, Caliendo decided to try his stuff on stage. The first night did not go over well.
"The first time I really did comedy was a talent show night at this dance club called Nitro in Milwaukee. I just bombed. The family members who came to see me were sure I was never going to try that again," he says.
But Caliendo was not deterred, and he tried comedy again. His gift for doing impressions started getting him booked around the area, including in Madison.
"The place that eventually became the Comedy Club on State was one of the first places to book me. I was doing a lot of stuff in Milwaukee, sometimes going to Chicago, but performing in Madison was always so much fun," he says.
Eventually, Caliendo started traveling the country performing on the college circuit. On the road, he learned how to string his impressions together, how to tell stories using the characters in his roster. The ability to weave in and out of different characters was a natural fit for sketch comedy, and in 2001, he became a cast member on Fox's MADtv.
MADtv provided Caliendo with his biggest audience up to that point, and his George W. Bush impression because a regular part of the show. Caliendo's take on John Madden, the former football star and color commenter for NFL telecasts, was popularized on that show and is still a cornerstone of his act today.
"I loved the cast members I worked with. The sketches I shared with Will Sasso will always be special memories," says Caliendo.
Sasso, who is also skilled at impressions, is today a master of six-second videos and has over two million followers on the short video network Vine. Other former cast members who made it big in comedy include Key and Peele, Andy Daly and Matt Braunger. But at the time the show received little attention.
"A big reason we didn't get noticed is that we were going up against Saturday Night Live. It is tough to be another sketch show going up against that institution," says Caliendo. "It's not just the legacy we were up against. They had a bigger budget, and the production values showed. Our show was pre-taped, they were live; there is still an energy to that -- the thought that anything can happen."
Caliendo also felt a bit of frustration with the creative process on the show.
"We did a lot of good things, but there was no identity to the show. I tried to pitch stuff, but it wasn't what the writers wanted. Honestly, it was kind of just a job for me, and standup was where I put my energy," says Caliendo.
Many comedians work day jobs while they perfect their standup. Caliendo's day job just happened to be a sketch comedy show.
Despite the ups and downs at MADtv, Caliendo's John Madden impression, which captures not only the former coach's vocal tone but also his proclivity for non sequiturs, helped the comedian secure a long-running spot on the Fox NFL Sunday pregame show.
"Doing the pregame was a one-off appearance originally. Jimmy Kimmel brought me on to do my John Madden voice for one sketch. But they liked it and kept having me on," he says.
After Jimmy Kimmel left Fox NFL Sunday to focus on his talk show, Caliendo took over as the show's resident comedian. He then realized how huge the show's audience was.
"Live sports are the only things that still get huge ratings," says Caliendo. All the audiences for things like sitcoms are so divided right now; shows are microtargeted to smaller and smaller audiences. But the NFL moves against that trend."
In 2009, Caliendo tired of touring and doing multiple TV shows, so he decided to do a show in Las Vegas. He and his wife had two young kids, and he wanted to be with home with them more.
But Caliendo found that doing standup in Vegas wasn't as much fun as touring.
"In Las Vegas, you start seeing the same types of people over and over again. The depressed people who got comp tickets from the casino because they lost so much gambling. The couple falling asleep who are only looking for an air-conditioned place to rest for an hour," says Caliendo. "They were tough crowds because they were from all over the country and the world; they didn't laugh at the same things. Some people only wanted to hear John Madden, some had no idea who John Madden was."
The experience made him appreciate the acts that were successful in Vegas.
"Vegas is much more of a singer's town. Music can be a little more universal. Doing comedy in Vegas gave me so much respect for what Cirque du Soleil does. You can take almost anyone from any place on Earth, put them in a Cirque du Soleil show and they are blown away," says Caliendo.
Caliendo decided it was time to refresh his career. He left Fox NFL Sunday and started working for ESPN.
"I loved the Fox show but doing the predictions and the skits every week got repetitive. It was formulaic, and there wasn't a lot of room for creativity. ESPN really gives me latitude to do what I want to do, to write what I want to write," says Caliendo.
The creative freedom at ESPN allows Caliendo to poke a bit of fun at the ESPN brand, including 30 for 30, ESPN's somewhat bombastic documentary series covering important events and people in sports history.
"I love 30 for 30; some of those are really moving and inspiring. At the same time, they take themselves so seriously. So when I wanted to do a parody of it, I wasn't sure what they were going to say, but they couldn't have been more supportive," says Caliendo.
His newer impressions on ESPN have proved to be quite popular. Caliendo says he now gets as many requests to do the voice of ESPN's Jon Gruden as he gets to do John Madden.
By 2013, Caliendo's kids were a little older and his ESPN schedule was a little more relaxed, giving him the opportunity to focus on standup.
"Last year, I went around to clubs instead of theaters. Smaller venues where I could work out some newer stuff. It's given me a renewed energy," says Caliendo.
The material worked out in the clubs provided the basis for the current tour.
"I'm really happy with this tour. It's got sports jokes but it's not all about sports. It's got new impressions -- Liam Neeson seems to be a favorite -- but also stories from my family. It's clean comedy, not because I want to sell more tickets but because that's the comedy I like to do," says Caliendo.
After more than a decade on television, Caliendo feels happier than ever.
"With two kids at home, I only want to be away two weekends a month. I'm grateful to be in a place in my life where I can pick and choose the shows I do. I'm lucky."