Some WordPress prompts are easy. This is not one of them.
“What is the best concert you’ve been to?”
That sounds simple enough until I start scrolling through the memory bank and realize I’ve been blessed to see some truly great ones. Not just good shows. Not just “they played the hits and sounded decent” shows. I mean nights that still feel special years later.
So instead of pretending I can pick one clear winner, I’m going to cheat a little.
Here are four concerts that could all make the case.
On April 14, 2018, we saw Jimmy Buffett and the Eagles in Orlando. That one was special before the first note was played. Just before the concert started, we watched a SpaceX launch rise up in the distance. That’s a pretty strong opening act.
It was the only time I got to see Jimmy Buffett, and he was good. But the Eagles were epic. Even without Glenn Frey, they delivered. When Don Henley stepped up and said they would be playing for more than two hours “because we can,” it felt like the beginning of something unforgettable. And it was.
Then there was Stevie Nicks and Billy Joel in Nashville on May 19, 2023. Stevie was fine, but the real moment came at the end when she sang “Landslide” with Sheryl Crow. That was one of those performances that stays with you.
She and Billy also teamed up for “Stop Draggin’ My Heart Around,” which was a great concert moment in itself. But when Billy Joel took the stage, the place came alive. He didn’t just play songs. He rolled through a lifetime of hits, and we were still singing them together all the way home.
On February 24, 2024, we saw Sting and Billy Joel in Tampa, and that one may have been even better. Sting was exactly what you would expect Sting to be — cool, talented and seemingly incapable of aging like a normal human being. Billy joined him for “Every Little Thing She Does Is Magic,” which was a great surprise.
Then Sting returned the favor during Billy’s set, coming out for “Big Man on Mulberry Street” in a sharkskin suit. The seats were great. The performances were great. The whole night was great. And yes, I would absolutely see Billy Joel again if I ever get the chance.
But then there’s Toto.
On March 2, 2026, we saw An Evening With Toto in St. Augustine. I’ve seen Toto four times now, and they’re still my favorite group. I’m hoping number five happens this August.
We had great seats, dead center in the third section, though honestly, St. Augustine’s amphitheatre doesn’t really have a bad seat in the house. The seats were reasonable. The sound was excellent. The night was beautiful.
And even though Steve Lukather is the only original member still in the band, and Joe Williams is the almost-original lead singer who has long since earned his place, Toto still sounded like Toto. That matters. Some bands become nostalgia acts. Toto still feels alive.
So what was the best concert I’ve ever been to?
The Eagles may have been the most legendary.
Billy Joel may have been the most fun.
Sting and Billy together may have been the best overall show.
But Toto?
Toto was the one that felt the most like mine.
And maybe that’s the real answer. The “best” concert isn’t always the biggest, the loudest, the most famous or the most impressive. Sometimes it’s the one that hits you in the right place, with the right songs, on the right night, with the right person beside you.
By that standard, I’ve been to more than one best concert.
And I’m perfectly fine with that.
Those are all great shows and hard to pick a favorite. I’ve seen most of them too!