Twenty years ago, Little Big Town seemed to be at the end of its rope when it came to establishing a foothold in Nashville. The country quartet had two failed record deals in the rearview mirror, with no real prospects.

“We were broken and we just sat down and wrote this record,” says Karen Fairchild Rolling Stone. “In a way, it was the best time because no one was looking over our shoulders while we were making music.”

This record would be Little Big Town’s breakthrough 2005 album The way here. Up until this point, the band had enjoyed moderate success with their self-titled debut in 2002. But Fairchild and her bandmates Jimi Westbrook, Kimberly Schlapman and Phillip Sweet couldn’t help but feel like they were going crazy in the mud, and some in the industry even viewed the group as “damaged goods.”

So Little Big Town decided to go all out and went into the studio with producer Wayne Kirkpatrick with nothing to lose. The goal was to not only capture the sound they had always envisioned for the band – a hearty mix of country, gospel and bluegrass – but also to take a risk and release it independently.

“(They were) things we had to say and get out,” Fairchild says The way here. “Put the demons out of our heads and realize that we can make the music we want to make.”

After its release The way here became a huge success, eventually selling over a million copies and reaching platinum status. The album spawned four hit singles, including two Top 10 hits, “Boondocks” and “Bring It on Home” (the former of which is still achieving tremendous success on streaming services).

“It’s not surprising that it was the breakthrough,” Fairchild says of the album. “Because it was the most honest, it was translated with that kind of emotion and meaning.”

Little Big Town became Music City’s star – albeit unconventional – and occupied a prominent position within country music that the group has held for over two decades. They’ve added country classics to the genre (“Little White Church,” “Pontoon,” “Girl Crush,” “Better Man”) and sold-out arena tours, including one with Sugarland that wrapped up in Nashville last week. Not to mention four Grammy Awards and numerous ACM and CMA awards.

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“The consistent story – and what has drawn me to the band most over the years – is strength and a willingness to take risks,” says Fairchild.

On Monday night, they add a holiday special to their resume Christmas at the OpryPremieres at 8 p.m./ET on NBC. The special is partly linked to the group’s latest LP, The Christmas recordwhich features traditional holiday fare, originals and seasonal country songs like “If We Make It Through December” by Merle Haggard.

“We’ve been singing Christmas music for a long time,” Fairchild said. “It’s something we’ve wanted to do for almost 25 years, but then we also did other studio recordings, went on tour and played with kids.”

Little Big Town hired top producer Dave Cobb to take on the project and met at Cobb’s studio in Savannah, Georgia, which the producer decorated with a Christmas theme to give the group a “home for the holidays” atmosphere.

“He’s adventurous and spontaneous,” Fairchild says of Cobb. “And he’s a music historian. When you reference something, he immediately knows what you’re talking about and points to something else, which is very inspiring.”

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When it comes to the pantheon of great vocal groups, Little Big Town’s harmonies could fit well alongside Fleetwood Mac, the Mamas & the Papas and Crosby, Stills & Nash. According to Fairchild, that was intentional.

“We knew that if we wanted to have a long career, we had to have a recognizable sound based on the harmonies,” she says. “Not just individual voices, but you treat the harmony almost as if it were a lead singer.”

Founded in 1998, Little Big Town’s long, winding history begins in the late 1980s at Samford University, where Fairchild and Schlapman attended the Alabama school and were both members of its vocal ensemble.

“We took the bus to a choir camp,” Fairchild remembers. “(Kimberly) sat right behind me and I introduced myself. We got along well and have been close ever since.”

Fairchild and Schlapman stayed in touch after graduation and “through all life changes.” In the mid-1990s, Fairchild was living in Nashville to pursue her musical dreams, and Schlapman wasn’t far behind. The two met again for lunch and began to think about their respective careers.

“The Chicks were huge (back then),” Fairchild remembers. “And we said, ‘We don’t want to do a girl (band) because nobody’s going to do it better – this is the best thing there is.'”

Her Eureka moment happened right then. Fairchild and Schlapman began playing around with the names of their favorite singing groups and what they liked about them: The Mamas & the Papas and Fleetwood Mac became the template for what they ultimately wanted.

“We thought, ‘No one has really done a mixed group (two female and two male singers) in country music,'” Fairchild says. “It took us a while to find the right people because we knew it wouldn’t be easy if we stuck together for long.”

Cue Sweet and Westbrook. Years earlier, Westbrook and Fairchild had crossed paths on tour when both were playing in other bands. While the groundwork for Little Big Town was being laid, Westbrook’s name was suggested to Fairchild and Schlapman. Fairchild remembered how great Westbrook’s voice was and called him.

“Once the three of us sang together, it was really good,” Fairchild says. “He drove from Birmingham to Nashville and he and Kimberly just got along so well, so much in common and such great chemistry.”

According to Fairchild, the group’s missing piece had to be “someone who sounded like they smoked all day, so the harmonies would basically be harder.” That would be sweet. “We were overwhelmed by his voice,” she says, “that smoky, big, hugely textured voice that we wanted.”

More than 25 years later, Little Big Town’s four original members are still intact, and Fairchild and Westbrook married in 2006. The group has become a family through harmony.

“We lived together so much,” Fairchild says. “Unfortunately, we buried family members together. And we’ve experienced some of the greatest highs we’ve ever experienced while having children. And we were always together.”

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Recently, Little Big Town had the honor of singing at the tree lighting ceremony at Rockefeller Center in New York. During their rendition of “Have Yourself a Merry Little Christmas,” which they cover The Christmas recordit started to snow.

“It was a little manna from heaven, you know?” Fairchild says. “You experience these little magical musical moments of absolute beauty and think: ‘I’m so happy that I still get to do this.’”