It Had to be Harry

Last night at Ravinia, as I prepared to see one of my favorite performers once again, I found myself transported back to the very first time I heard him.

I remember it like it was yesterday.

It was 1989. I was a 15-year-old freshman at Bishop Noll Institute when I bought the soundtrack to When Harry Met Sally. There was this young artist named Harry Connick Jr. who performed a song called "It Had to Be You." I was instantly hooked.

I quickly discovered he had released an earlier album called 20, and I found a copy as soon as I could.

A few months later, just before my birthday, Harry was coming to the Chicago Theatre. I knew I had to go, and I knew exactly who I wanted to bring with me—my Grandpa.

My grandfather loved the great crooners. He introduced me to legends like Frank Sinatra, Dean Martin, Tony Bennett, and one of my all-time favorite albums, Dave Brubeck's Time Out. I loved everything about music then—the album artwork, the sound, and the stories behind every song. Every time I visited Grandpa, I would dig through his record collection and listen to albums on that enormous record player that looked more like a dresser than a stereo.

I remember spending what felt like an astronomical amount of money—$80 for two tickets. I apologized to my parents because I couldn't take them. They understood and happily became our chauffeurs for the evening.

We had third-row seats, right next to the speakers. I worried that Grandpa might find it too loud.

I couldn't have been more wrong.

Every note that came from that stage sounded perfect and melodic. The music washed over us, and for those few hours, it felt magical.

Since then, I've seen Harry dozens of times. Over the years, I've had the privilege of meeting many of his band members, people I now proudly call friends. Jazz musicians are some of the coolest, most down-to-earth people you'll ever meet. Their vibe is different. They are true ambassadors of the music, and I've always admired their skill, dedication, and pursuit of perfection.

Maybe it's the smaller crowds. Maybe it's the intimacy of the venues.

Or maybe it's simply the music.

Decades later, I had the opportunity to meet Harry with my wife. We attended a meet-and-greet in South Bend, and it became one of those moments we'll never forget.

As we posed for a photo, Harry complimented my white sport coat.

Before I could even respond, my wife quickly fired back, "Really, Harry? I'm standing here in this beautiful white dress, and you notice his jacket?”

She completely caught him off guard.

Harry laughed, turned a little red, and immediately began complimenting her dress. It was all in good fun, but it became one of those priceless moments that you couldn't script if you tried. To this day, we still laugh about it.

That's the beautiful thing about music and the artists who create it. They don't just provide a soundtrack to our lives—they give us memories, stories, and moments that become part of our family history.

I've also converted my wife, family members, and several friends into Harry Connick Jr. fans over the years. They've all come to appreciate what I've known since I was fifteen years old. Harry's performances are more than concerts; they're experiences.

But as special as all those moments have been, there will never be another first time—sitting beside Grandpa in the third row of the Chicago Theatre, listening to every note that floated through those speakers.

Harry Connick Jr. will always hold a place in my heart and soul. His music is a gift, and so are the memories that have come with it.

And this show, like every show, reminded me that Jerry Weldon, Dion Tucker, Mark Braud, Arthur Latin, Neal Caine, Nathaniel Williford, and Andrew Fisher are more than a band. They are an experience.

Kudos to these profound jazz masters for sharing their extraordinary talents and giving us memories that last a lifetime.

Every time I hear "It Had to Be You," I'm reminded that some songs don't simply play in the background of our lives…

They become part of our story.

And for the last 36 years, Harry Connick Jr.'s music has certainly been part of my Cherishing Life journey.

Damian Rico is the Marketing and Community Relations Director at Hospice of the Calumet Area. The opinions expressed are his own.