The Art of making a Set list

I've written well over a hundred songs at this point. Some, if I'm honest, aren't so great. But many — at least in my opinion — are pretty good. Songs about sad cowboys, cats, aliens, pleasant mistakes, and broken-down trucks.

When I play, I want to play those songs. They're mine, and there's nothing quite like watching someone connect with a song that started as nothing more than an idea I scribbled down at my kitchen table.

But I also love playing covers — usually older ones. Act Naturally. The Gambler. Buddy Holly's Not Fade Away. Songs that have been around long enough to feel like old friends, both to me and to whoever's listening.

So the question becomes: how do you mix those two things into a set list that actually works?

I don't think there's a perfect formula, but I've landed on a few things that help.

Covers are an invitation, not a crutch. A familiar song gives the crowd a handhold — something they can sing along to, something that tells them "you're in good hands here." I try to use that to my advantage, not lean on it so hard that the night turns into a jukebox.

Originals need company they trust. I've found an original lands better when it's got a familiar cover on either side of it, especially early in a set before people know who we are. It's easier to take a chance on a song about a sad cowboy when the band just proved they can also nail The Gambler or Country Roads.

Energy and mood matter more than genre. I am beginning to think that it is less about "original vs. cover" and more about the shape of the set — where it starts slow and builds, what key the song is in, where it needs a breather, where it needs to peak. A cover and an original can serve the exact same emotional purpose in a set; the label doesn't matter nearly as much as the feel.

Save some trust-earned real estate for the deep cuts. By the back half of a set, once the room's warmed up and on our side, that's when I'll take the bigger swings — the stranger originals, the ones that are more "us" than anything else out there.  This seems to work better after we have established our “chops” and show that we can do covers in our own style.

Read the room and let the list bend. I'll build a set list going in, but I don't treat it as gospel. If the crowd's locked into the covers, I might slide in a few more originals than planned. If they're really digging the originals, I'll let that breathe a little longer before pulling back to something familiar.

At the end of the day, a set list isn't really about originals versus covers. It's about trust — earning enough of it early that people are willing to follow you somewhere new, and then rewarding that trust with something only you can give them.

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