Todd May still has more questions than answers as rare Lilybandits performance approaches

Todd May said he reached a point some years back where he believed Lilybandits would never again take the stage, owing in part to the reality that two members – Trent Arnold and Jason Gonzalez – had settled into lives and routines far from Columbus. This idea was further reinforced when founding drummer Keith Smith died in November 2022, right around the time the band reissued its 1995 debut album, Shifty’s Tavern, releasing it to vinyl for the first time.

“I had known Keith since we were 15 or 16 years old, and we were in our first actual band together that tried to write songs and play shows when we were teenagers,” May said in early June at the Clintonville Cup O Joe. “It was always me and him from the get-go. And that made me really sad, because not only did I lose a friend who I’d known for almost 40 years, but it was the end of the idea that [Lilybandits] would ever play music together. Because when Keith was alive, even when we weren’t playing, I had this idea that it was still possible.”

Recently, however, a confluence of factors has combined to reunite the roots-rock band, whose members will share the stage for the first time in more than 15 years when they headline a concert at Natalie’s Grandview on Thursday, June 5, joined by Two Cow Garage. Foremost, the group recently reissued its sophomore album, At Thirty-Three and a Third, from 1999. Travel plans then conspired to bring Arnold and Gonzalez back to Ohio, with the two then coordinating their visits to create a window in which the band members could gather for a day of rehearsal before hitting the stage, with the concert serving as a means to both celebrate the re-release and to honor their late drummer, whose role will be filled at Natalie’s by Secret Studio cofounder Keith Hanlon.

“And Keith and Jason played in a high school band together,” said May, who described this connection with Hanlon as essential to the spirit with which the reunion is taking place. “It seemed like it was the only way we could pull it off. I mean, I know a lot of fantastic drummers who could do the job, but it felt important to have it be someone who wasn’t just a hired guy.”

The mix of joy, melancholy and reflection surfaced in our conversation – emotions perhaps heightened by the hours May spent in the company of Smith’s son the evening before we spoke – ripples throughout At Thirty-Three and a Third, a record on which May, then in his late 20s, takes a view of himself, his relationships, and his career prospects that is often far more mature than his somewhat tender years might suggest. On “Top,” the singer and songwriter expresses a desire to make better use of the time he’s been afforded on Earth, while the reflective “Past Few Days” sees him surveying the wreckage of a failing relationship and uncovering gratitude for the patience he’s been granted amid his missteps. “You always wait for me to learn,” he sings.

May said similar themes have always been present in his songwriting, including an awareness of the finite nature of time, the urge to wrangle with his own romantic shortcomings, and a desire to confront larger questions of purpose and identity – the answers to which he currently feels more distanced from than he did in his earlier years. “I feel like I know less now than I did then,” he said, and laughed. “I have more experience, but it doesn’t answer any of those questions for me. … I don’t know. I’ve been accused of oversentimentality before, but that reflection isn’t like, oh, I miss the good ol’ days! It’s trying to figure out how that experience, how that relationship, and how those mistakes that you make begin to change who you are, where you are, and where you go next.”

For May, the recording of Thirty-Three and a Third, which the musicians captured in a series of visits to a pair of New York studios over the course of a year in the late 1990s, coincided with a point in time in which the possibilities often felt endless. “We’re recording in these amazing studios in Williamsburg and Alphabet City, and it really felt like something,” he said. “We were a bunch of kids from Ohio, and it was like, what are we even doing here? And it’s a contagious thing, where the more those things happen to you, the more you kind of expect them to happen. And then at some point we were all thinking that maybe we could actually make a living doing this, and this could be our job.”

And yet, even at the time May harbored a jaundiced view that surfaces most clearly on “Vertigo,” a song on which the pinnacle begins to come into view, but the musician can’t avert his eyes from the growing height that will accompany the inevitable fall. 

Stepping into Lilybandits, May said he briefly harbored dreams of being the next REM, adjusting this sense of expectation over time as his sense of identity became less entwined with his musical pursuits.

“It’s a very American thing to totally attach your identity to what you do for a living. And at some point in 1999, certainly, I was fine with that, and being a singer or songwriter, that was my identity,” May said. “Now I’m older and I have a kid, and I don’t feel the same way about it that I did then. And I still love doing it, clearly, or I would not. But it’s not like, ‘This is what I am. I have to do it.’ And it’s a very liberating thing to be like, I’ll do what I want to do, or I’ll do what I can. I don’t need it to be my identity anymore.”