Bush was raised outside of Knoxville in Sevierville, Tennessee, a small town at the base of the Smoky Mountains that was also the hometown of Dolly Parton.

[2] During college, Bush began to connect with Atlanta's growing music scene, often begging his way into clubs, witnessing first-hand success from bands like R.E.M.

Recent producing and songwriting collaborations include Ellis Paul, Laura Bell Bundy, Matt Nathanson, the dB’s, Martin Johnson of Boys Like Girls, Pretty Little Liars star Lucy Hale, and up-and-comers including Kristina Train, Larkin Poe, Canaan Smith, Lauren Alaina, Jaida Dreyer and Alana Springsteen.

In 1990, Bush played guitar and sang backup vocals on Big Back Porch Songs, an album by the Hyras.

The Hyras had made plans for future performances, but Annie had accepted a job in Miami, Florida; Bush replaced her.

[9] After a year of performing, the two drove to Knoxville where they rented two days of studio time, where they recorded 14 original songs, assisted by their producer Danny Browns.

[10] They continued performing shows in southeastern college towns, and Bush reached out to various talent agents with their demos; Jen Stark, an intern at Atlantic Records, received a copy, which resulted in commotion about them amongst the company.

"[9] The album was a success in garnering attention; Atlantic Records held a release party for the two, and they were signed to the label that night,[9] in New York.

[11][9][12] The duo released the self-titled album Billy Pilgrim in 1994, in association with producer Hugh Padgham, who had a group of London musicians overdub the master with additional instruments.

In 1995 they opened on a worldwide tour for Melissa Etheridge, but copies for Billy Pilgrim weren't made in time to be promoted throughout it.

"[13] Sales for Bloom were underwhelming, and with increasing focus on Hootie and the Blowfish, Atlantic Records dropped the duo in 1996.

Billy Pilgrim went silent temporarily as did Bush; he occasionally played at Eddie's Attic, and did production work Ellis Paul, Beth Wood, and Evan and Jaron.

Bush and Hyra collaborated for a "farewell" tour, and although they simply meant they were taking a hiatus, news spread they were disbanding.

Nettles had recently concluded her time in other bands and met Atlanta singer-songwriter Kristen Hall at a bar and discussed their country music endeavors together.

[16] In 2003, Bush met with the two at a Starbucks to discuss starting a band together; the trio officially formed Sugarland the next day.

[17][18] The name was suggested by Hall; its derived from the town of Sugar Land, Texas, and was picked since it reflected the "sweet" tone of the band.

[4] They found success performing live in Knoxville, and Bush bought his first cowboy hat on eBay in 2003 to prove to his friends he was taking the new endeavor seriously.

On August 13, 2011, during their Incredible Machine Tour at the Indiana State Fair, the stage collapsed due to high winds, killing seven people and injuring 58 others.

Fulfilling their pre-established plans, Bush's final performance as Sugarland before the hiatus was at Mandalay Bay Resort and Casino on September 2, 2012.

[28] He began playing and writing for those he had worked with in the past, although they were reluctant to give him an opportunity because they did not know anything about how he performed separately; he realized then that the momentum from Sugarland would not carry over into his potential solo career.

[4] In July 2013, after being drawn to the music and design of the mobile app My Singing Monsters while watching his son play, he expressed his praise of the game on Twitter.

The game's director Dave Kerr responded suggesting a collaboration and Bush agreed, performing the mandolin for a monster representation of himself, the "Shugabush".

[35] My Singing Monsters would later feature a cover of "Love or Money" (called "Shugabush Island"), with Bush doing a gibberish rendition of the lyrics.

He collaborated with the best in his field to ensure people weren't showing positive reception simply because he was famous, including Will Jennings, Paul Overstreet, Bob DiPiero, and James Blunt.

Bush was fascinated meeting people who were both fans of Sugarland and "Trailer Hitch", but having rarely heard him sing in the former, were surprised to find that he sang the song.

Bush had been given the green light for a second solo album, and Hyra was a carpenter and performed casually, so no plans for a reformation were made at the time.

[47] "Forever Now (Say Yes)", written and performed by Bush, became the new theme song for the TLC reality series Say Yes to the Dress when their 14th season premiered on March 4, 2016.

[55] In 2019 Bush formed a new band with his brother Brandon, and friend Benji Shanks called Dark Water.

[60][61] 52 | New Blue was released on September 30, 2022, and consisted of songs that reflected Bush's folk rock music of the 1990s and Billy Pilgrim.

[65] Bush's brother Brandon is a former member of the rock group Train, and also tours with Sugarland, Billy Pilgrim and Kristian's solo project as a keyboardist.