The summer of 1999 marked the arrival of McCain's third album, Messenger, which included a second Top 40 hit, the Diane Warren-penned "I Could Not Ask For More."

About the same time, he hosted "Inside Music With Edwin McCain", a syndicated show on the Sirius radio network.

It was his first live concert DVD, recorded at The House of Blues in Myrtle Beach, South Carolina.

Lost in America contained three singles: "Truly Believe", "The Kiss" and live-favorite "Gramercy Park Hotel", which pays homage to the New York City landmark and its colorful patrons.

On January 22, 2017, McCain sang the American National Anthem at Gillette Stadium for the AFC Championship Game between the New England Patriots and Pittsburgh Steelers.