Murray Attaway and Jeff Walls became friends in high school, and had played together in a punk band called Strictly American (which also included Curtis Crowe, the future drummer of Pylon).

At the time, Attaway's close friend Rhett Crowe, who was learning to play bass with guidance from Walls, joined the new band which became Guadalcanal Diary, referencing the 1943 war memoir of that same name.

Guadalcanal Diary quickly attracted attention with its frequent live shows in the Athens and Atlanta music scenes and throughout the Southeast.

The album was well received by critics and enjoyed significant airplay on US college radio stations, drawing comparisons to fellow Georgia band R.E.M.

Due to new family commitments and exhaustion from heavy touring, the band began to drift apart; they chose to break up in order to preserve their friendships.

In the early fall of 1989, they played their collective final show in a free performance at Legion Field on the University of Georgia campus, and organized by the Tau Epsilon Phi fraternity's Nu Chapter.

He began recording with producer Tony Berg in 1992, along with various guest musicians, including Jackson Browne, Aimee Mann, Benmont Tench, and Nicky Hopkins.

Despite Geffen's high budget and innovative promotional tactics, including the giving away of the first 50,000 copies, the album fared less well commercially than Guadalcanal's releases.