After another solo effort, Until Then: A Collection of Hymns, he signed on as a vocalist and trumpeter in the venerable Christian group NewSong, joining their ranks in 1993. Billingsley led the band to new heights of popularity, scoring a series of CHR chart-topping hits and launching their most successful album to date, 1994's People Get Ready. He left NewSong in early 1996 to return to a solo career, releasing Change and Live!, both with Crest Music in 1997. Between Now and Then marked a switch to Pamplin Music, and resulted in a Top 20 appearance on the contemporary Christian chart in 1999. It was followed by the next year's Marks of the Mission.

In 2002, the performer began a longstanding role as worship pastor at Thomas Road Baptist Church in Lynchburg, Virginia. He then signed with Perpetual Entertainment Group, which released Secret Conversation and We Bless Your Name in 2003 and 2004, respectively. A move to Red Tie Music brought Christmas and a collection of hymns titled Enduring Treasures, both in 2007, and Hope, Love and Music and Classics in 2008. Credited to Charles Billingsley and the EW Band, Extraordinary Women 09 Live Worship was recorded at an EW conference in Greenville, South Carolina, and that same year, God of the Ages: Live at Thomas Road landed on the Billboard Christian Albums chart.

Soon after, he began releasing music with his own label, Charles Billingsley Concert Ministry, which issued 2011's Never Forsaken, the anniversary collection 20 and related live celebration In Concert, and 2014's Only Jesus before the singer signed with Stowtown Records. They released 2016's Right Here. Produced by Grammy winners Keith Everette Smith and Seth Mosley, it featured the duet "See You Again" with Meredith Andrews. ~ Jason Ankeny & Marcy Donelson