Will Dailey

Will Dailey is an American independent recording artist, performer and producer. His sound has been described as being vintage inspired while having characteristics of AM rock, pop and big hooks.

He has released albums with Universal, CBS Records, Wheelkick Records and JS Music Group. Dailey has released seven full-length albums since 2004. His seventh full-length record, Boys Talking, was released physically in late 2024 and arrived on streaming platforms on February 27, 2026. His full-length album, National Throat, came out on Wheelkick Records, on August 26, 2014. It directly followed Dailey's choice to split with a major label and use Pledge Music to create his album. Dailey is a Neighborhood Salon Luminary at the Isabella Stewart Gardner Museum in Boston, where he has performed in the Calderwood Hall RISE Music Series and at Third Thursdays events. In 2023 he began the $10 Dollar Song, a project created with the intention of prioritizing human connection over algorithms and analytics where his song "Cover of Clouds" can only be heard one time at a listening station at live shows. A 2017 article in The Simple Dollar highlighted his work ethic and indie ethos, labeling Dailey a "middle-class musician. In 2024, Dailey performed at the inaugural Folk, Americana and Roots Hall of Fame induction ceremony, paying tribute to Richie Havens and Pete Seeger. The ceremony was broadcast as a special on PBS and nominated for an emmy.

Based out of Boston, he is notable as being a 7-time winner in the Boston Music Award: Best Male Singer-Songwriter in 2006, again on December 2, 2009 and December 2, 2012 and Album of the Year and Artist of the Year December 14, 2014 and Male Vocalist in 2015 and 2016. The first single, "Sunken Ship", was a finalist in the 2013 International Songwriting Competition, received heavy radio play and received Song of The Year in the New England Music Awards. The album was released exclusively on vinyl three month prior to official release date. It premiered on Billboards Heat Seekers chart at #18 and won Album of the Year in the New England Music Awards April 19, 2015 as well. In 2009 and 2010, Dailey released Torrent, which involved the artist digitally releasing a burst of new music approximately every three months, and then compiling that material, along with bonus material, as a physical and digital audio package twice a year.

Dailey is also a part of the John Mellencamp and Stephen King musical project Ghost Brothers of Darkland County.