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Early years

Crosby's musical endeavors began at the age of 13, where he was noted in Guitar Player Magazine as a promising guitarist of the future. Growing up, Crosby spent his teen years in Humboldt County, California. He often recorded home demos with nothing more than a guitar and a drum machine, sometimes a bass player with him as well. He nearly signed with Shrapnel, a guitar-based label, but turned it down to work on his budding songwriting skills. Crosby eventually left Rancho Cotate High School in Rohnert Park, California, to do home study and begin his own band, which he dubbed VAST. Much like fellow alternative rock/industrial band Nine Inch Nails, Crosby was the only member but found a touring band who knew the songs well enough to play with him live.

After sending multiple demo tapes to nearby radio stations in his home state of California, the band got a contract with Elektra Records. VAST released a teaser of their upcoming debut album Visual Audio Sensory Theater, titled VAST Is..., which featured the first four tracks of the album. The track "Touched" received considerable amounts of airplay on local radio stations before capturing the attention of a mainstream audience, when it was featured in the Dana Brown surfing film Step into Liquid. It also received exposure when it was played briefly in the trailer for the movie The Beach (even though the song never made it to the actual soundtrack). NBC also used it as a promo song during TV show advertisements.

After Visual Audio Sensory Theater, Elektra pressured Crosby to go back to the drawing board and craft an album that was accessible to more listeners, but still retaining the distinct sound of the last album. After two years of recording, VAST returned with 2000's Music for People. The album featured a more rock-oriented sound, and benefited from major-label funding by allowing Crosby to work with the New Bombay Recording Orchestra in India. Turmoil was abundant during the album's recording and rehearsal process as Crosby constantly fought with record executives over the music's direction and former backup guitarist Rowan Robertson wishing to leave VAST to begin his own solo career. By the end of the album's recording process, Robertson had left VAST, and Crosby reluctantly moved forward with the band. Music for People provided the band with MTV airplay through their lead single "Free"'s music video, with the single charting on the Billboard's Hot 100, and hitting No. 2 on the Modern Rock Tracks. The band became a relative success after Music for People, but the album's poor sales and lack of a second charting single led to tension between Elektra and Crosby. In late 2002, Elektra terminated VAST's contract.

2blossoms years (2005–2009)

After a short tour for Nude, the band released 2blossoms's first release, A Complete Demonstration, which was a collection of early demo tracks during the Visual Audio sessions. The album was a limited-edition piece and sold quickly due to popular demand. Then in 2006, VAST released Turquoise & Crimson, a double-disc collection of all the tracks that were released as bundles online in 2004 online under his label. Originally it was only available through the 2blossoms website, but it was later released to retail stores. During the tour for the double album, VAST played at CBGB's, and, in late 2006, released Live at CBGB's on their 2blossoms record to moderate sales. After multiple tours, VAST went back to the studio and recorded their first all-acoustic album, April.

The release method for April was, once again, unorthodox. In 2006, Crosby released an online version of the acoustic album online with ten tracks. April was mostly recorded only by Crosby and an acoustic guitar, with minimal use of bass and drums. After the online release, Crosby said he was unhappy with it and went back to the studio to add four new tracks and a whole new track listing. The cover featured fan-made artwork, and the album received a traditional release in stores. The album was not as well received by critics and fans, but was modestly embraced. Crosby later said that he only had it in him to do one album like April, and that it was his favorite VAST album.

Crosby also released a span of solo albums entitled Generica with him and an acoustic guitar throughout 2007 and 2008, culminating in a collection in 2009. The music would later find its way onto VAST albums being reworked into a full-band setting on future release Me and You.

Despite an expected documentary entitled Closed Romantic Realism, 2008 saw the release of an EP for Crosby's science fiction novel Bang Band SiXXX. The EP, containing six songs, is closely related to his older music with lots of electronics leading the music instead of acoustic guitars. Crosby claims it is a return to his older, darker sound. The EP is entitled Bang Band SiXXX: Relay EP. Many of the songs have become live staples at shows.

In May 2009, Crosby released Me and You and a North American tour in support of the album. Me and You contains songs from Crosby's Generica series reworked into a full-band setting. Crosby also is planning on launching a release of the album in which you can purchase the album and allow the proceeds to go to a charity of the purchaser's choice. Me and You is currently only released through retail.