In 1990 and 1991, Chilton took time off from touring and recording to live during the warm months in a tent on his land in rural Tennessee and work on clearing trees and framing his planned house, a project he was never to complete. In 1993, Chilton recorded Clichés, an acoustic solo record of jazz and pop standards, in New Orleans' Chez Flames studio with Producer Keith Keller. The record was inspired by a short solo acoustic tour of the Netherlands featuring Chilton, alternative country luminary Townes Van Zandt, and several other Musicians in January, 1992. Chilton's final two studio albums featured his band and continued his pattern of mixing together songs from pop, soul, blues, gospel, R&B, swing, and country music. A Man Called Destruction (1995), like High Priest, featured a mix of covers and originals and an expanded band that included horns, keyboards, and occasional backup Singers, and was released in the U.S. on the relaunched Ardent Records label. Chilton took an enlarged edition of his band on Late Night with Conan O'Brien in July 1995 to promote the album, playing the song "Lies". This was Chilton's second appearance on national television in less than a year; in October 1994, he appeared on The Tonight Show with Jay Leno with the reformed Big Star. Chilton's final solo studio record, Loose Shoes and Tight Pussy (1999), featured only his trio, and was named after an old off-color joke made infamous in 1976 by Politician Earl Butz. Chilton released one more album as a solo Artist, the 2004 CD Live in Anvers, which featured him playing a show in Belgium with a pick-up band of European Musicians.