CR 023: Will Dailey on Connecting with Audiences While Staying True to His Art

The Boston singer-songwriter discusses his latest album, “Boys Talking,” and his unorthodox career choices.

Will Dailey, photo by Pat Piaseki

Over the course of his 20-year career, Will Dailey has consistently forged his own path. In 2014, the singer-songwriter broke free of his major label contract in order to go the indie route. In 2023, he launched a “$10 Song Initiative,” enabling attendees at his concerts to pay $10 (or however much they can afford) to listen to a prerecorded, seven-minute, unreleased song—one they can’t hear anywhere else. That project served as a catalyst to his latest release—a full-length album, Boys Talking, which is available only through Dailey’s website, and will not be offered on streaming platforms.

These unconventional decisions, he says, are driven by his desire to connect with listeners on a personal level. “I’m upset about everything that’s going on in our world. What can I do about that? Well, maybe this isn’t the repair or the fix, but it’s one push in a direction that values the human next to the human. It’s just a pebble in the ocean, but what if we al…