As a teenager Eaglesmith hopped a freight train out to Western Canada, and began writing songs and performing. He is known for writing songs about trains, rural life, dogs, drinking and farming have been covered by some of the most popular country stars including Miranda Lambert and Allan Jackson. Down and out characters dealing with loss of love or livelihood, and quirky rural folk also populate his songs. Eaglesmith's full band shows are textured performances, reminiscent of the variety shows of the 1970's - funny, tender countrified rock'n'roll. Comedic monologues interspersed between songs round out the show.