The Williamsons trace their roots back to 1998, when Donnie Williamson founded the Homesteaders Quartet. He wanted to sing on a limited basis, but overwhelming demand soon led the group to over 100 dates per year and ultimately led the group to go full-time. The group ultimately changed its name to The Williamsons, featuring Donnie, his wife Lisa, bass singer Darin Hebert, and baritone singer Michael Helwig. (Helwig previously sang with The Wilburns and the Stamps Quartet.)