Ware River Club formed in 1998 when Matt Hebert recruited former members of other groups that had been based in New England. Matt Cullen formerly played his guitar for Kevin Salem and the Sighs. Ray Mason had contributed bass to the Lonesome Brothers as well as to his own band. Keith Levrault previously spent time as a drummer for such outfits as Blood Oranges. And, like new bandmate Cullen, he had also worked with Kevin Salem. Soon, the newly formed group was in the studio, working on The Bad Side of Otis Ave., which was released that same year. The album also featured contributions from the Scud Mountain Boys' Stephen Desaulniers and the Johnson Boys' Duke Johnson. Bob Hennessey, whose credits include the bands Treefort and Angry Johnny, also appeared on the recording. Ware River Club's music, especially "Wanna Be With You," "Green Thumb," and "Brambles," soon made its way to indie radio in Europe and the U.S. "Akron" found its way onto Luxury Liner 4, a compilation issued by Glitterhouse. By 1999, the band sported a new lineup. Johnson, who had appeared on The Bad Side of Otis Ave., joined full-time to play bass. Former Joe Interlande Band drummer Don McAulay also joined the group. The band began opening shows for such artists as Emmylou Harris, the Jayhawks, the Connells, and Richard Buckner, among others. In 2000, Ware River Club went on to tour the U.S. following the release of the album Don't Take It Easy.