I Won 2025 Entertainer of the Year: But This is What That Really Means

For a long stretch of my career, everything worked.

One video kept me booked constantly. It landed TV spots, corporate work, and opportunities I couldn’t have planned for if I tried. If that video went out, I was usually the first call back. It did exactly what it was supposed to do.

That momentum took me to Las Vegas.

Through Mac King and his producer, Bill, I started doing shows in Laughlin, then Reno, and eventually filling in for Mac himself at Harrah’s. I still remember standing backstage knowing Mac King was sitting in the room. Right before I walked onstage, he leaned in and said, half joking, half not:

“Just remember… this is my f***ing room.”

Then the music hit. I walked out. And I delivered.

Those years led to longer contracts, bigger rooms, and eventually my own show on the Las Vegas Strip at Mandalay Bay. From the outside, it looked like success. On the inside, it was pressure — financial, personal, and relational. The cost wasn’t obvious yet, but it was real.

Around that time, I was part of a show at Planet Hollywood called Amazed. That’s where I met Jeff Civillico. He was living in Florida then, and we connected immediately. When the opportunity came up, I didn’t sugarcoat it. I told him, You need to come out here. You need to do this show.

Jeff didn’t dabble. He sold a rental property, packed up his life, and moved to Las Vegas. We lived together with a rotating group of married performers, all chasing something we thought would last.

That’s when Jeff told me about an idea he couldn’t shake.

He called it Win-Win Charity — a way for entertainers to give back by performing for kids in hospitals. No fees. No spotlight. Just showing up. Jeff would coordinate with hospitals and place performers where they were needed most.

I said yes without really understanding what I was saying yes to.

When the Vegas shows collapsed and my marriage was stretched thin, I went home to Minnesota to save my family. Jeff kept building. And when I told him I wanted to bring Win-Win to Minnesota, he backed it immediately.

My first hospital visit changed everything.

Before I performed, I was handed a list of things I wasn’t allowed to say. No “How are you?” No “I hope you get better.” A nurse saw the confusion on my face, grabbed my arm, and quietly said, “Sweetheart…”

That was the moment I understood where I was.

Later, during a bedside visit, I performed for a little girl while a nurse stood nearby. I noticed the nurse getting emotional and panicked, convinced I had done something wrong. Afterward, I quietly asked her if I’d crossed a line.

She said, No. She’s terminal. And this is the first time we’ve seen her smile in a long time.

That stopped me cold.

In that moment, I understood I wasn’t just performing for a child. I was giving her family something they could hold onto. I was giving the nurses a rare, human moment inside a room that usually doesn’t get one.

That day replaced the meaning of success for me.

I began building a relationship with Children’s Minnesota, performing monthly and appearing on their internal hospital TV station. During COVID, when in-person visits stopped, Win-Win pivoted to virtual programming. From my basement studio, we broadcast weekly shows to hospitals across the country.

Win-Win Charity grew into a 501(c)(3) nonprofit. A board was formed. Paid hosts were hired. The reach expanded nationally. I joined the board and continue supporting performers and programming as the organization evolves.

In 2025, Win-Win Charity named me Entertainer of the Year.

I’m grateful for the recognition. But the title didn’t change me.

A hospital room did.

Every time I walk into one now, it’s never, I have to do this.

It’s always, I get to be part of this today.


Help Bring Joy Where It’s Needed Most

If you’ve ever felt the power of a shared smile or a moment of laughter during a hard time, you already understand the heart behind Win-Win Charity. Every performance, every broadcast, every hospital visit is made possible by people who choose to be part of something bigger.

Your donation doesn’t just support programming — it helps create human moments in places that often feel inhuman. It gives families memories. It gives nurses relief. And sometimes, it gives a child their first smile in a long time.

Be part of that moment. Make a donation today. Or find out more below.

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