Unwed Sailor has had a number of contributors, but since the group's inception in 1998 it has been guided by the vision of Johnathon Ford. Born in Oklahoma, Ford had been a member of Roadside Monument and Pedro the Lion. As a result of his own songs not melding with either, he formed Unwed Sailor in Seattle and has since been based in other cities including Chicago and Washington, D.C. Before moving to Chicago, Ford recruited David Bazan (Pedro the Lion), K.C. Wescott (The Vogue), and Melissa Palladino (Damien Jurado, Jen Wood, Danielson Famile) to record the 1999 EP Firecracker, originally released on Seattle's Made in Mexico and reissued on Philadelphia's Burnt Toast Vinyl. In 2001, Ford was joined by guitarist Nic Tse for The Faithful Anchor, with help from Dan Burton and Joe Brumley of Early Day Miners and Matthew Johnson of Roadside Monument. That same year, Ford collaborated with Ester Drang and members of Oklahoma country band Lasso for a joint project called Circle of Birds. Ford and Tse got help from drummer Matt Putman along with Matt Depper and James McAlister of Ester Drang for The Marionette and the Music Box, issued in 2003. In 2006, Unwed Sailor kept busy with The White Ox and an EP, Circles. Little Wars arrived in spring 2008.