Settling in San Francisco, Gentry became a digital producer & songwriter. He won 3 NCSA songwriting awards, formed the Night Watchmen & released 5 band & solo records from 2001 to 2005. Gentry co-wrote the album "Santa Fe Sky" with Dave Hoover in New Mexico in 2006. He released his solo album "No War" 2 months later. He then spent 3 years touring the US & Europe. In 2008, he recorded "Avond" with Jesse Brewster, an English adaptation of a Dutch song by Boudewijn de Groot & Lennaert Nijgh. His self-titled EP came out in 2009.
Back in CA, he played the Bay Area heavily & was featured singer on John Brown’s Hip Hop song "No Games". He then recorded an album of English adaptations of Dutch artists' songs titled "Within A Sigh & A Curse". His 6th & 7th European tours followed.
His 15-song album "Human" was released in 2013 & exhausted, Gentry left SF. He spent 4 years in Mexico & MN. During that time, he founded GB Media & Creative to focus on helping other entrepreneurs & musicians. Gentry made New Orleans his home in 2017. In November 2018, he released "Environments", a new album of solo, original piano music.