Top 10 Chesney Songs We Love Performing Live

If you've ever been to one of our shows, you know that performing Kenny Chesney's music is more than just playing songs — it's about capturing the spirit of the beach, the stories of small-town life, and the soul of country music with a laid-back twist.

We're lucky enough to bring that energy to stages all over, and whether we're rocking a beach party, a county fair, or a honky tonk on a Saturday night, there are a few songs that never fail to light up the crowd.

Here are our Top 10 Kenny Chesney songs we absolutely love performing live — and why they keep making the setlist.

1. No Shoes, No Shirt, No Problems

This one is the anthem. As soon as we strum that opening chord, people are already raising their drinks and singing along. It captures that "escape to the islands" vibe that fans live for.

2. When the Sun Goes Down

We always say, "When the sun goes down… this crowd turns UP." It's the ultimate duet (even if we have to pull someone from the band to sing Uncle Kracker's part), and the energy is just electric.

3. She Thinks My Tractor's Sexy

This one gets everyone grinning. It's playful, it's cheeky, and it's a great excuse for a little crowd participation. We've seen line dances break out mid-song more than once!

4. American Kids

A newer favorite that hits hard with nostalgia. The lyrics paint such a vivid picture of growing up in the South, and we love how it brings multiple generations together singing every word.

5. Summertime

We bring this one out during outdoor shows and festivals — because nothing says summer like this track. It's smooth, fun, and gets everyone in that laid-back, barefoot mood.

6. You and Tequila

One of our slower moments in the set, and a powerful one. Whether we do it acoustic or with full band, this song always quiets the crowd and brings out the emotion — it's a beautiful storytelling moment.

7. Beer in Mexico

This one speaks to the soul of anyone who's ever wanted to hit pause on life and chase the sun. It's a fan favorite and always gives us a chance to stretch out with a little instrumental flair.

8. Don't Blink

A reminder to live in the moment — and a crowd favorite that usually gets a few teary-eyed fans singing along. We love the connection this one brings every time.

9. Out Last Night

This one is just fun. It's our go-to party starter when the crowd needs a boost. It always has people up and dancing, remembering their own wild Friday nights.

10. There Goes My Life

We often close the show with this emotional ballad. It's heartfelt and raw, and people feel it — every word. It's a beautiful way to bring the night full circle.

We know we're not the Kenny, but when we hit the stage, we channel every bit of his spirit, energy, and connection with the crowd. His music brings people together — and performing these songs live is an honor we never take for granted.

Got a favorite Kenny Chesney song you want to hear at our next show? Drop us a message or let us know at the merch table. And don't forget to catch us when we roll in to your town!

The Poets And Pirates,
Keeping the island country dream alive — one show at a time 🌴🎸