ifitbeyourwill Podcast #168 • Trippers & Askers

Jay Hammond Wants You to Think About What You've Tried to Do

There's a specific kind of musician who resists the pull of genre entirely — not out of contrarianism, but because the music simply won't cooperate. Jay Hammond, the Durham-based songwriter behind Trippers and Askers, is that kind of musician. His forthcoming album Tried to Do's, due May 2026, doesn't so much blend folk, jazz, and indie rock as it lets them bleed into each other until the borders stop mattering.

Hammond came up in Jackson, Tennessee, took guitar lessons from a guy who toured with Carl Perkins, got deep into jazz, then got derailed — productively — by the Brooklyn indie scene of the mid-aughts. Dirty Projectors. Phosphorescent. Thurston Moore. The kind of shows that make you rethink what an instrument is supposed to do.

Tried to Do's is a grief record, though Hammond bristles at tidy summaries. The title lifts from something Nikki Giovanni used to say — never published, just spoken — about the value of the attempt over the outcome. The album moves cyclically, opening and closing on arrangements of the same traditional piece, designed so that if it looped forever, you might not notice.

One song, Remembering, is, in Hammond's words, a couples therapy song. He says it plainly, without apology. That directness is the point.

A release tour hits Asheville, Durham, and up the East Coast through New York, with UK dates to follow. His Bandcamp goes deeper if you're willing.