On 14 November 1998, Cummings and, a briefly reformed, The Sports performed at the Mushroom Records 25th anniversary concert. His next solo album, "Spiritual Bum", had Cummings as record producer and was issued in June 1999. He returned to an acoustic, melancholic sound. Cummings also had his second novel, "Stay Away from Lightning Girl", published in 1999, which described an aging musician and his band. In 2001, he released "Skeleton Key" followed by "Firecracker" in 2003, "Close Ups" in 2004, "Love-O-Meter" in 2005, "Space Travel" in 2007, and "Happiest Man Alive" in 2008. On 1 May 2009, his memoir, "Will It Be Funny Tomorrow, Billy" was printed, which his publishers described as a series of anecdotes from his childhood through thirty years of the music business and his family relationships. In October 2010, his 1988 album "Lovetown" was listed in the top 40 in the book, "100 Best Australian Albums".