Born in Matsqui, British Columbia, Jackson was the second of four children. Raised in Cariboo country, central BC, during his early years, he was well acquainted with the Williams Lake Stampede.
While collecting empty beer bottles around the rodeo grounds he would hear the sounds of guest artists as they sang their country songs from the stampede stage. Jackson was hooked on the cowboy style and the music that went with it.
Fast forward to 1998. Jackson was confined to home after surgery on a broken knee cap. He says his life has never been the same – and all for the better! While sitting around, he dragged out an old guitar – he now had plenty of time on his hands. Then he remembered a promise made, a debt unpaid. Jackson then volunteered to sing for anyone who was unable to get out and about. Then he met Jessi Jo Charles and things changed dramatically. Jackson and Jessi were soon singing duets and performing 15 to 20 times/month.
Although the Jac & Jessi duo is no longer active, Jackson continues to be available for events. Jackson solos or teams up with Kayla Patrick & Bob Glidden, and other friends who play and/or sing. He was a feature performer on the 2006 and 2009 Alberta Men of Country Music show. He has since appeared with North American fiddle champion Calvin Vollrath and band, and continues to take bookings with them.