After spending the summer of 1998 touring to promote "Homecoming", Andy and Adam left Craig’s Brother to form the band Too Bad Eugene. In December of that year, guitarist Ryan Key traveled from Florida to California to audition for the band. Ryan later memorialized his experiences auditioning for Craig’s Brother in the song “Rock Star Land" by Yellowcard. Ryan was joined shortly thereafter by Dan McClintock from Inspection 12. At one point, the two of them represented Craig's Brother at the Cornerstone Festival as an acoustic duo. After touring vigorously the majority of 1999, the band found themselves without a van or money to buy one in August. When the band decided to go home and regroup, Ryan decided to go back to Jacksonville where he got a job with Sean Mackin and eventually joined Yellowcard. The band returned home and started to work on their second album, "Lost at Sea". After recording finished in Vancouver, British Columbia, Canada in January, Dan McLintock also opted to return home to Jacksonville, rejoining his old band Inspection 12. In fall of that year Heath also announced that he was quitting. The band continued to play shows, experimenting with a number of drummers and guitar players, including Garrett Baldwin, Justin (Juice) Cabrera and Steven Neufeld.