How Little Big Town Went From The Boondocks To A Band Celebrating Its 25th Anniversary (Exclusive)

Karen Fairchild, Jimi Westbrook, Kimberly Schlapman and Phillip Sweet know a lot about working together.

Yes, the quartet makes up the multi-award-winning country music band Little Big Town, but they are also a family unit and have lived four different lives together as one over the past 25 years.

Now the band celebrates its musical heritage with a Biggest hits The album will be released on August 9th, and in October they will start their Take Me Home tour with the duo Sugarland.

“I think about 25 years of memories and how many tours we did with them in the early years and how it’s come full circle now,” says Sweet when we ask him what made the duo Jennifer Nettles and Kristian Bush the right touring partners (and additional voices on the band’s cover of Phil Collins’ “Take Me Home”).

“I think the song was Kristian’s idea too, but just getting back together and recording it felt like a beautiful full-circle moment,” he says.

“They’re like family,” Fairchild adds.

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

“I think we had been in the music business for a while and we were each going our own ways. We had no idea what we were doing, but we knew enough about the chemistry that had to develop offstage to make the stage special,” Fairchild says of the group’s humble beginnings (she and Schlapman met in college in Alabama and were soon joined by Westbrook; Sweet completed the band after an audition).

“It couldn’t just be about the few hours on stage, it had to be about the other hours too. We just wrote down a few simple things. It’s easy to make rules when you’re broke!” Fairchild adds, laughing about the band’s early mission. “They weren’t really rules. They were more things we wanted to be guided by.”

Although the band has now released 10 studio albums (11 with Biggest 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 here”) hasn’t been easy.

The group didn’t land their first number one hit until 2005, after being dropped by their record label in 2002. But even the song’s success was not without personal heartache.

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

“It took our connection to a new level and touched on things that families share and that no one else really understands or knows,” she says.

“I think this is probably the moment for all of us,” Westbrook says, reflecting on the loss of his friend. “These are the things you go through with family. Realizing at the time that our careers had been so front and center, you thought, ‘Oh, we’re still living our lives, and no matter what we do, these are the moments that matter.'”

As their careers soared, so did their lives: Westbrook and Fairchild married in May 2006, and Sweet married his wife the following year.

Schlapman also found love again and married Stephen Schlapman in November 2006.

And now, with 25 years of experience, Little Big Town will continue to move forward (and speak its mind).

The band has a unique ability to sing about drinking on pontoons and the difficulties young women face as they grow up, lending their vocals to songs about birth and growing up in the boonies as well as songs about love and loss and everything in between.

“I’m very proud of us as a band for being willing to say things that other people might not say,” says Fairchild. “‘Sugar Coat’ ultimately wasn’t a commercial success because some people, the gatekeepers, felt that nobody wanted to hear that from a woman, which -”

“The gatekeepers are all men,” Schlapman interjects.

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

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

“We enjoy making music together and inspiring each other to be more creative. It’s really fun when you do it with people you enjoy being around. It can be a wonderful life,” says Sweet.

“And we laugh at jokes that no one else gets,” Fairchild jokes. “That’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.