In the late-'90s, Little Big Town was still a little country band looking for their big break. They thought they found it with Mercury Records, but the label failed to produce any singles or albums for them. When they eventually signed with Sony's Monument label, they were caught in a hailstorm of criticism for a manufactured image that didn't really reflect who they were. That struggle to establish an identity lead the harmonizing team to write "Boondocks." Phillip Sweet explained in a Songfacts interview: '"Boondocks' was inspired by us just wanting to speak about who we are and what we're about. Because there seemed to be a little bit of confusion there at Sony when we were signed there that we were a put-together band, or we weren't country, we're too slick. And nowadays you wouldn't even get those kind of questions, but at that time it just seemed really strange. And I don't think radio really understood who we were yet. So we just wanted to write this, and it was therapy for us and it was a chance for us to really make a statement about our roots. And that's really what it was."
After the nightmarish experience with Sony, the band members halfheartedly went back to their day jobs while playing occasional gigs. Sweet remembers working a handful of odd jobs, including telemarketing and clerking at a liquor store. He was even hired to give away free lessons for a dance studio. Westbrook worked as a valet, often pulling his hat down so he wouldn't be recognized by friends when he parked their cars at music industry events.
Kimberly Schlapman lost her first husband, Steven Roads (who was also the group's lawyer), to a heart attack in 2005. The experience inspired the song "You Can't Have Everything" from their 2010 album, The Reason Why. She married Stephen Schlapman in 2006.
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