[2] After finding work as a demo singer, Larry joined the group Restless Heart in 1984 at the recommendation of the band's keyboardist Dave Innis, with whom Stewart had attended college.

Titled Down the Road, the album produced a Top 5 country hit in the single "Alright Already," along with a number 34 follow-up, "I'll Cry Tomorrow," and "We Can Love," which peaked at 62.

This album also included a cover of Kevin Welch's 1989 single "I Came Straight to You", and the song "When I Close My Eyes", which was later a Top 5 hit in 1996 for Kenny Chesney.

In 1994, the same year that Restless Heart disbanded, Stewart made two contributions to Faith Hill's debut album Take Me as I Am, co-writing the single "But I Will" with Troy Seals and singing duet vocals on "I've Got This Friend".

Stewart joined Nashville's Breezewood Productions in 2014 as chief operating officer focusing on promising new talent while continuing to bring music through his association with Restless Heart as well as a modern solo career.