The country vocal quartet Little Big Town began with Kimberly Roads and Karen Fairchild, who began singing together at Samford University in Birmingham, Ala. Fairchild moved to Nashville in 1994 to work for a booking agent on Music Row. Roads moved a year later. After they reunited, they invited Jimi Westbrook (a friend of Fairchild's) to sing with them and accompany them on guitar. He moved to Nashville in 1998. Through one of Fairchild's co-writers, they met another singer-guitarist, Phillip Sweet, who solidified the quartet in 1998.
The quartet found a supporter in the CAA booking agency, which helped them secure a contract with Mercury Records. They made their public debut on the Grand Ole Opry in 1999. However, the Mercury deal fell apart although they had landed publishing deals to sustain them. In time, they signed to Sony's Monument Records, but the label dropped them after the release of the group's 2002 album.
In their personal lives, Westbrook's father died. Sweet and Fairchild both divorced, and Roads' husband Steven died unexpectedly of a heart attack. (A lawyer, he had assisted with many of the quartet's legal contracts.) The group did not disband, but Westbrook, Sweet and Fairchild all returned to day jobs.
However, songwriter Wayne Kirkpatrick offered to pay for a new recording. They agreed. Top musicians such as Gordon Kennedy (guitar), Jimmy Lee Sloas (bass), Mountain Heart's Adam Steffey (mandolin), Union Station's Jerry Douglas (Dobro) and Ron Block (banjo) pitched in. Equity Records (co-owned by Clint Black) released their second album in 2005, The Road to Here, which included the hit "Boondocks." The following year, the album was certified gold.
Westbrook and Fairchild married in 2006. The ensemble also received their first CMA nominations that year, for Horizon Award and vocal group. After releasing their third album, titled The Road to Here, on Equity, they moved to Capitol Nashville, which reissued the album in late 2008 with bonus tracks. They embarked on their first headlining tour in 2009.