Prior to releasing her debut album, Kasey Chambers had resigned herself to the fact her music would never reach the mainstream. Her unique voice, combined with songs that recalled artists such as Emmylou Harris, Steve Earle, Townes Van Zandt and Lucinda Williams—hardly chart toppers in 1999—wasn’t really a recipe for success. And yet that’s exactly what The Captain turned out to be, the title track winning Chambers an ARIA Award for Best Female Artist in 2000 and even infiltrating popular culture due to a placement in acclaimed mob drama The Sopranos. Though only 22 when the LP was released, Chambers was already a seasoned professional, having spent more than a decade touring with her family group, the Dead Ringer Band. The Captain was also a family affair, with brother Nash producing, and father Bill playing guitar. Recording the album on Norfolk Island, Chambers draws on the everyday for lyrical inspiration, be it her upbringing (“Daddy sang me Rodgers/Just to make everything alright,” she sings in “Southern Kind of Life”), travelling(“Don’t Talk Back”, “Mr. Baylis”), and the Norfolk Island pines (“These Pines”). The career-making title track, meanwhile, was inspired by a relationship on the island, as told through the eyes of her future self.