If you’ve been to Summerfest in the last five years, you might recognize the high-energy man with a microphone, dancing around in bright, multi-colored suits with infectious enthusiasm: Christopher Gilbert. Gilbert is the official emcee of Summerfest’s American Family Insurance House, the intimate venue that hosts some of the big names at Summerfest for about 200 people ahead of their larger performances.
If you stop by the House, you’ll see Gilbert working the crowd, dancing and keeping the energy up for the show. But who is the man behind the microphone? (And does he really wear a suit every day?) We sat down with the choreographer, teacher and self-proclaimed ambassador of the arts in Milwaukee to talk about how he got here, what makes the perfect concert vibe and more.
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This is your sixth year as the emcee of Summerfest. How did you get started?
It’s a very out of the blue story. You never know who’s watching, so always stay prepared, stay honest, and be true to yourself, because there is someone literally always watching. I received a random email six years ago that was like, “We’re creating [The American Family Insurance House] and this is going to be the next thing that adds to what Milwaukee already has to offer and to how legendary Summerfest is. Would you be interested?” And I was like, “Doing what, exactly?” And they said, “Emceeing.”
I told them I’m not an emcee, I’m a choreographer. But they told me “No, we think you’d be great for the job.” And what I’ve realized from this is that there’s always going to be somebody that sees something in you that you don’t see in yourself. That’s the beauty of life, that we can all highlight something in each other. That’s a huge salute to my American Family Insurance team, because they saw something in me that I didn’t see.
How was that first year?
I remember thinking, I think they just want me to be myself. But in my mind I was also like, I haven’t been here, so this is a learning moment and experience. So I was asking a lot of questions and trying to take it in. There was a point halfway through the first year of me doing it where I asked, “Is it cool if I just go off the cuff and vibe?” Because I’m a people person and I like to interact with people and not read off of cards. And they said yeah. From that moment on, I threw the cards out and just unleashed myself.
What’s your approach to emceeing?
It feels very personal to me, because obviously I’m a 414 kid, and it’s fitting that it’s called the AmFam “House,” because for me it’s all about hospitality. With these artists that are world-renowned, it’s like they’re just coming to hang out in the living room with me and 200 other people. So I try to make it as cool as possible. Over the years, I’ve added different things that I feel add to the experience. For example, we do a vibe check. I’m a dancer, so it only makes sense that I dance with people, so we dance before we get into the show, and even though I’m not a great singer, we all sing together.
It’s just all these little things that I feel we need more of in our world, which is that connection that’s honest and true. There’s so much that tries to divide us, so finding moments where you choose to show up for people or get an escape, there’s a level of importance to that. I feel like I have a responsibility, especially being a kid that’s from here, to show up in that way for people to have an experience.
What’s the greatest joy of being the emcee at Summerfest?
My biggest goal in life is to be the official artistic ambassador for the 414, to push Milwaukee toward a greater light, and to have that light shine in the way that I’m able to have happen inside of that house with those people – most are from here, but there are so many that fly in, too. That’s the greatest joy. It’s cool to be able to say I was part of that conversation, so when people fly back to where they came from they share about the experience they had in this room with these people and how this community felt like home.
An experience is not something that is temporary. With the right experience, the right feeling, when they come together, it can be a statement. People don’t forget statements. So every time I touch the stage, you have to give them experience. They could have chosen to be anywhere else in the world during that moment in time, so you have to make it an experience, to make it count. That’s one of the greatest joys, is providing a real experience for people to look at Milwaukee in the way that they should look at Milwaukee.
OK, we need you to tell us a little about the suits.
In 2013, I started wearing suits. At the time, I threw out all of my streetwear clothes, which sounds very crazy, and I started thrifting suits. I had a whole collection of thrifted suits, and then I just never looked back. Then when I was working in LA, I met a friend that was a stylist from overseas and he sent me something with patterns. And if you know me, I’m big on patterns, always colorful. From that moment on, I was addicted. I never wore a basic suit again. I live by this quote that I always say – that I don’t want my best dressed day to be in a casket.
Now there’s so many young kids that are like, “I’m thinking about [getting] a suit.” I’m like, you can never go wrong with it, you’re always presentable, you can always walk into any space, and they’ll be like, “OK, that person’s about something.” People may not know my story, but they know I’m going somewhere in life because of how I’m presenting myself.
So do you actually wear a colorful suit every day?
I do, I do. I’ll say 98% of my closet is suits. The other 2% is all Milwaukee-based clothing lines. And I do that on purpose because I want people when they don’t see me in a suit – if they do, which is very rare – to ask what I’m wearing and then I can show that I’m investing in what I believe in, which is Milwaukee.
What else have you been working on lately?
Mr. New York, a well-known DJ here in Milwaukee, has an R&B night at the Aurora Pavilion stage at Summerfest this Friday night [June 27] at 9 p.m. That’s a place to be if you’re going to be there on the grounds. I choreographed for his set, and then I put a team of dancers together that I’ve worked with since I was a kid, and also a few that I’ve met within like the last like year, so just bringing the community together from all aspects and dancers from all walks of life. That’s going to be an experience.
Is there anything else you’d like to share?
I love Milwaukee. Period. Team 414 all day. I’m a firm believer in speaking things into existence, and I feel like Milwaukee will be one of those places – and already is, but will be even more as time goes by – that’s a place people need to be. It is the place to be.

