[1] An independent artist who self-releases his albums, Myles has been able to gain an increasingly large audience, in part because of his active touring schedule and in part because of his cross-genre musical collaborations, which include a single made with the rapper Classified that became the biggest-selling rap single in the history of Canadian music.

He attended Mount Allison University in Sackville, New Brunswick and graduated in 2003 with a Bachelor of Arts (Honours) in political science.

He was chosen to represent New Brunswick by a public vote, and commissioned to write a song about the Bay of Fundy's historic Hopewell Rocks.

Unbeknownst to him, the music bar's sound technician recorded the performances, capturing relaxed live shows.

[14] In the same year, Nova Scotia rapper Classified featured Myles on the song "The Day Doesn't Die" from his album Handshakes and Middle Fingers.

Although he was left uncredited in some cases, this song gained him more exposure in the hip-hop world as well as a larger fan base.

[15] Also in 2013, Myles released the double album In the Nighttime, on which he gave each of his two separate performing personas (mellow and jazz-influenced on the one hand, beat-oriented and pop-influenced on the other) its own disc of music.

The idea of the album suggested itself in part because of Myles' annual "Singing For Supper" tour in Eastern Canada every December, which raises money and donates food for those in need.

[18][19] On October 4, 2014, Myles began hosting The East Coast Music Hour with David Myles on Saturday mornings, a new performance program in Atlantic Canada that blended two regional music programs - Atlantic Airwaves that aired in the Maritimes and The Performance Hour that was broadcast in Newfoundland and Labrador.

[20] In January 2015, Myles was named Touring Artist of the Year at the CAPACOA (Canadian Arts Presenting Association) Awards for the 2013–14 season.

[23] On September 15, 2017, Myles released his tenth studio recording, Real Love, a nostalgia-tinged ode to classic rock and roll.

[27] Myles also released his first Children's book in the Fall of 2018 from Nimbus Publishing based on his song "Santa Never Brings Me a Banjo", with illustration by animator Murray Bain.