First established in 2005, the band consisted of singer and guitarist Ryan Boldt, bass guitarist Chris Mason, guitarist Burke Barlow and drummer Lucas Goetz. Pianist and organist Geoff Hilhorst joined the group in 2009 after the release of their breakout album Winter Hours. Founding member Burke Barlow played guitar until 2012 when he left the group and was replaced by Clayton Linthicum. Founding Member Lucas Goetz left the group in late 2014, after which the band went on hiatus. In 2017 Chris Mason officially left the group.[2]
Boldt has also released one album, Broadside Ballads, as a solo artist independently of the band, in 2015.[4] Two further albums, Broadside Ballads Volume II in 2020 and Broadside Ballads Volume III in 2024, were released as Deep Dark Woods albums.
^Certain award groups do not simply award one winner. They acknowledge several different recipients, have runners-up, and have third place. Since this is a specific recognition and is different from losing an award, runner-up mentions are considered wins in this award tally. For simplification and to avoid errors, each award in this list has been presumed to have had a prior nomination.
^Jeanette Stewart, "The Sheepdogs fetch Juno nods; Sask. acts nab five nominations". Saskatoon Star-Phoenix, February 8, 2012.
^Jeff Dedekker, "Western Canada's top musicians get their awards". Calgary Herald, October 2, 2012.
^Carolyn Thompson, "Canadian Folk Music Awards gala strikes the right chord; Performance Night featured Matt Andersen, Mike Stevens, Cindy Church and Susan Crowe". Telegraph-Journal, November 19, 2012.
^"Saskatchewan gets eight WCMA nominations". Regina Leader-Post, June 5, 2014.
^"New band Magic nabs five Juno nominations". Telegraph-Journal, January 29, 2015.