Milsap has remained one of country music's best-loved and most successful artists despite the lack of radio airplay in the last decade. In 1993, he left RCA for Liberty and released the album True Believer which failed to achieve significant radio airplay, although the title track song scored No. 30 on the country chart. In 2000, Milsap resurfaced with a two-CD set, 40 No. 1 Hits, featuring a new single "Time, Love, and Money". The new collection earned a gold record although the single failed to score on the charts.
During 2004, Milsap worked with producer Jerry F. Sharell to record his first non-country album since the early 1970s, Just for a Thrill. The project was a collection of American popular/jazz music standards which earned Milsap a Grammy award nomination that year. In 2006, Milsap signed with his former company RCA and returned to a mainstream, contemporary country music style with the album My Life. The first single was "Local Girls" which reached No. 54.
In 2009, Milsap released a two-CD set entitled Then Sings My Soul which featured 24 hymns and gospel songs, including "Up To Zion". "Up To Zion" was co-written by Gregory James Tornquist and Noreen Crayton and became a number one hit on the southern gospel charts. On May 12, 2010, he was part of a Gaither Video Taping.
At age 68, Milsap released his new studio album Country Again in July 2011. The new CD is a return to a more traditional country sound. The first single, "If You Don't Want Me To", is a previous Milsap recording from 1980.
Milsap has remained as one of country music's most popular concert performers and continues to tour regularly for his many fans across the country.