Will Dailey has built a dynamic DIY career as an acclaimed independent songwriter, recording artist, performer and artist advocate. Often described as a venn diagram of multiple genres with a rich vintage vibe channeled through his authentic and energetic performances, it inspired famed rock journalist Dan Aquilante to call him “the real deal”. Through his how label he as appeared on the top 20 on the national Billboard Heat Seeker chart twice and he’s won 8 Boston Music Awards including Album of the Year, Artist of the year and songwriter of the year 3 times.
He has shared the stage and studio with Eddie Vedder, Willie Nelson, Roger McGuinn, Kay Hanley, G Love, Steve Earle, and Tanya Donelly. In June of 2013 he was featured on a Stephen King/John Mellencamp project produced by T Bone Burnett called Ghost Brothers Of Darkland County and, in that same year, also released an original song he wrote inspired by Jack Kerouac's Tristessa. Dailey has played at Farm Aid four times alongside Neil Young, Willie Nelson, Dave Matthews and John Mellencamp. His new album, Golden Walker, was released summer of 2018 and hit #1 on Billboards Northeast Heat seekers. The Boston Herald called the album: “A new peak” and named it an album of 2018.
During the Covid crisis Dailey got to work and raised over 32K for non salary employees of venues in Boston, other artists and the City of Chelsea through online performances.