The group's third album, entitled The Green Room Serenade, Vol. One, seemed to be a breakthrough album.
In 1999, after the release of Gift Horse, guitarist and vocalist Gene Eugene passed away.
In 2001, the group continued as a trio, releasing Real Men Cry on BEC Recordings.
In 2006, The Lost Dogs returned to the studio with help from Steve Hindalong (also of The Choir, who co-produced the Dogs’ previous two albums), Matt Slocum of Sixpence None the Richer, and Jerry Chamberlain of Daniel Amos, and created what most fans are calling one of their best albums yet, The Lost Cabin and the Mystery Trees.