How Little Big Town Went from the 'Boondocks' to Celebrating 25 Years as a Band 'Willing to Say' What Matters (Exclusive)

Karen Fairchild, Jimi Westbrook, Kimberly Schlapman and Phillip Sweet know a thing or two about banding together. 

Yes, the quartet composes multi-award winning country music band Little Big Town, but they’re also a family unit, and for the last 25 years, they’ve moved through four different lives together as one.

Now, the band is celebrating their musical legacy with a Greatest Hits album on Aug. 9, and they'll kick off their Take Me Home tour with duo Sugarland in October. 

“I think of 25 years of memories and how much we toured together with them in the early years and just how that has come full circle,” says Sweet when asked what made duo Jennifer Nettles and Kristian Bush the right tour mates (and additional voices on the band’s cover of Phil Collins’ "Take Me Home").

“I think it was Kristian's idea, too, about the song, but just getting back together and doing it felt like a really beautiful full circle moment coming together," he says.

“They’re like family,” adds Fairchild. 

Family is perhaps the most important thing to Little Big Town: they each have their own (Schlapman is married to Stephen Schlapman and Sweet to wife Rebecca, while Fairchild and Westbrook are married to each other, and all three couples have children) but the band is one big family unit, too. 

“I think because we had already been in music for a while, each of us on our own paths, we had no idea really what we were doing, but we knew enough about the chemistry that had to happen off the stage in order to make the stage special,” says Fairchild of the group’s humble beginnings (she and Schlapman met in college in Alabama and afterwards were soon joined by Westbrook. Sweet completed the band after auditioning). 

“It couldn't just be about the couple of hours on stage, it had to be about the other hours. We just wrote down simple things. It's easy to make rules when you're broke!” Fairchild adds of the band's early mission with a laugh. “They weren't really rules. They were more the things we wanted to guide us.” 

Though the band now boasts 10 studio albums (11 with Greatest Hits) and has taken home eight Academy of Country Music awards, nine Country Music Association trophies and three Grammys, their rise to fame (or as they might say, their "road to here") wasn’t easy. 

The group didn’t score their first No. 1 hit until 2005 after being dropped by their record label in 2002, but even the song’s success didn’t come without personal heartbreak. 

“When my husband died, they literally picked me up and carried me. They were my arms and my legs for so many days,” says Schlapman, whose first husband, Steven Roads, suffered a fatal heart attack in 2005 just as the group was notching their first major hit with “Boondocks.”

"That took us to another level of bond and things that families share that nobody else really understands or knows about," she says.

“I think that's probably the moment for all of us,” says Westbrook, reflecting on his friend’s loss. “Those are the things you walk through with family. At the time, realizing our career had been so in the forefront, you go, ‘Oh, we still live life, and no matter what we're doing, these are the moments that matter.’” 

As their careers began to skyrocket, so too did their lives: Westbrook and Fairchild married each other in May 2006, and Sweet followed suit with his wife the following year. 

Schlapman found love again, too, tying the knot with Stephen Schlapman in November 2006. 

And now, with 25 years under their belt, Little Big Town will continue to forge ahead (and speak their mind).

The band is unique in their ability to sing about day drinking on pontoons just as well as they sing about the complexities young women face as they grow up, lending their vocals to tracks about being born and raised in the boondocks, yes, but also to tunes about love and loss and everything in between. 

“I'm very proud of us as a band for being willing to say some things that other people might not say,” Fairchild says. “‘Sugar Coat’ ended up not being a commercial hit because some people, the gatekeepers, felt like no one wanted to hear a woman say that, which — ”

“The gatekeepers are all men,” Schlapman chimes in. 

“Right. There's songs like that — and we didn't write that song, but it felt like ours — that are so meaningful. Same thing on ‘Daughters,’” says Fairchild. “There's some deep cuts that really are meaningful from a ‘saying something that matters’ perspective. Those are also, I think, the enduring songs that we'll look back on and go, ‘Wow. We said those things when nobody else really wanted to.’” 

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And, the band is still just as happy to be here as they were in 1999. 

“We enjoy making music together, and we inspire each other to be more creative, and that's really fun to get to do with people that you enjoy being around. It's like what a wonderful life that can be,” says Sweet. 

“And we laugh at jokes that no one else understands,” quips Fairchild. “It's 25 years of behind-the-scenes jokes.”

For more on Little Big Town pick up the new issue of PEOPLE, on newsstands everywhere now.