[2] The Randy Rogers Band recorded its debut album, Live at Cheatham Street Warehouse, at a music hall of the same name in San Marcos, Texas.

It was around this time that the band began performing outside of San Marcos, primarily at Nutty Brown Cafe and Amphitheatre in nearby Dripping Springs, Texas.

Two years later, the album Rollercoaster was released, producing two minor entries on the Billboard Hot Country Songs charts in early 2005.

Dreamer: A Tribute to Kent Finlay, released in 2016 on Austin-based Eight 30 Records, features Randy Rogers and Sunny Sweeney's duet "Between You and Me".

Randy Rogers Band and their song “Speak of the Devil” referenced in Showtime TV series Billions (“STD” 21:04).