Behind the Music: Bourbon Legend’s Favorite Songs to Play (and Why)

We’ve been asked a lot of questions over the years—what’s the story behind your name, how long have you been playing together, where can I get a shirt like that—but one of the most common ones we hear is, “What’s your favorite song to play live?”

It’s a deceptively simple question, but as we found out, it sparks a wide range of answers. So we posed that and a few related questions to every member of Bourbon Legend to see what songs fire us up on stage, which ones the crowd seems to love most, and which tunes surprised us by growing into favorites over time.

For David Brooks, what was once “Can You Run” has now been overtaken by “Mountain Annie,” a song from one of his favorite bands. What makes it so enjoyable? The banjo parts didn’t exist in the original recording—so he had to create them from scratch. That process of trial, error, and eventual mastery made the song deeply rewarding, especially during the jam section where the whole band gets to stretch out and experiment.

Matt Saunders had a different kind of connection. For him, “Follow You to Virgie” felt like fate. Long before it ever made it onto the setlist, he was driving to work, listening to it, and thinking, This would sound amazing with us. Sure enough, the moment he brought it to practice and played the opening riff, it came together almost instantly—one of those moments that reminds us how naturally this band fits together.

Vocalist Bill Reinking found himself drawn to “If It Hadn’t Been for Love,” a song that demands a full range of expression. As a singer, it’s a blast to belt out the chorus, and hitting those highs and lows gives every performance an emotional edge. Megan Rae found a similar kind of joy in the small details. “Fishin’ in the Dark” is a standout for her—not just because it’s fun to play, but because the pizzicato intro offers something different, evoking warm summer nights and outdoor shows, even in the middle of winter.

And then there’s Jim Lipnos, our guitarist and eternal vibe-watcher. One of his favorites is “Cleopatra,” a deceptively simple song that thrives on dynamic energy. That soft-loud-soft-loud rhythm gets the crowd moving—and him bouncing around on stage. “It’s just got that timing that makes people stand up,” he said, grinning.

When it comes to the songs that get the biggest crowd reaction, there were a few clear frontrunners. “Country Roads” was mentioned multiple times, and for good reason—phones go up, voices rise, and the whole room becomes one giant, singing family. “Sweet Home Alabama” earns a similar kind of love, according to Bill. And David shouted out both “Alone” and “Laundry Room,” two songs that start slow and delicate, only to build to a full-band crescendo that always ends in cheers.

But not every song was love at first play.

Some, like our original “The Legend of Johnny Mac,” took time to grow into. David admits it started off pretty basic, but as we kept playing it, it kept evolving—and now, it’s one of his favorites. For Matt and Jim, “Cleopatra” took some extra work to truly nail down, especially when it came to timing and that pesky bridge. Megan pointed out that songs in B-flat minor were initially tricky, but they’ve since become more comfortable. And Bill, despite his wide musical taste, had a tough time locking in the phrasing on “Something in the Orange.” Now? It’s a standout in his book.

There’s something special about watching a song transform—whether it’s a familiar cover that takes on new life, or an original that slowly finds its shape. And for all of us, part of the magic is sharing that process with the crowd. Every stomped foot, every singalong, every head bobbing to a tune they don’t even know yet—it all fuels the fire.

So next time you catch a Bourbon Legend show, you’ll know: the setlist isn’t just a list of songs. It’s a living, evolving story made up of personal milestones, band chemistry, and shared moments with all of you.

See you at the next one.

Have a favorite that we play or one that you want to hear?  Leave it in the comment section!