He started playing in a band with his parents when he was 13-years-old and later formed the band Early Tymz in 1990, where he initially met Troy.
He was diagnosed with prostate cancer in 2010, but recovered after receiving treatment.
He had four children with Tracy Nunan. The couple divorced in 2010 and lost their son, Hunter, to an overdose in 2015. His brother John Michael Montgomery also became a country singer.
He's worked with Toby Keith as part of Montgomery Gentry.