Little Big Town's musical style relies heavily on four-part vocal harmonies, with all four members alternating as lead vocalists.

Their second album, The Road to Here, was released that year, and received a platinum certification from the Recording Industry Association of America (RIAA).

1 singles "Pontoon", and "Better Man" along with the top 10 hits "Boondocks", "Bring It On Home", "Little White Church", "Tornado", "Day Drinking", and "Girl Crush".

[1] In the mid-1990s, Fairchild sang with the Christian vocal group Truth and was featured as a lead singer in a few of their songs.

She formed a duo called KarenLeigh with Leigh Cappillino, a member of Truth who joined the group Point of Grace.

The album produced the singles "Don't Waste My Time" and "Everything Changes", which peaked at 33 and 42, respectively, on the Billboard Hot Country Songs chart.

After Westbrook's father died, and Fairchild and Sweet got divorces, the band members got outside jobs while they continued to tour.

"Bring It On Home", the second single from the album, became Little Big Town's first top 5 hit on Hot Country Songs.

Unlike their first album, the group's members co-wrote the majority of the songs on The Road to Here along with Wayne Kirkpatrick, who also produced it.

[6] Little Big Town released A Place to Land, their third studio album and second with Equity, on November 6, 2007.

[7] Shortly afterward, they charted with Sugarland and Jake Owen on a live cover of The Dream Academy's "Life in a Northern Town".

In October 2008, Capitol re-released A Place to Land, which added four new songs, and the label promoted two further singles from the album, "Fine Line" and "Good Lord Willing".

The song, "A Ride Back Home", was released as the album's third single and was accompanied by a music video.

The album produced two additional singles in "Kiss Goodbye" and the title track, but both failed to reach the top 40 of Hot Country Songs.

"Pontoon" was released as the album's lead single on April 30, 2012, and became their first number one hit on Hot Country Songs in September 2012.

The band sang background vocals on Ashley Monroe's 2013 single, "You Got Me", featured on her 2013 release, Like a Rose.

Little Big Town performed harmony vocals on David Nail's 2014 album, I'm a Fire, on the song "When They're Gone (Lyle County)", co-written by Brett Eldredge.

They were featured on Miranda Lambert's 2014 album, Platinum, on "Smokin' and Drinkin'", a song which the band had considered recording.

Some radio stations were reported to have pulled "Girl Crush" from their playlists, in response to concerns from listeners who interpreted the song's lyrics to be about lesbianism.

[18] Billboard consulted radio program directors on its panel and found one who detailed a specific complaint from a listener.

The album's third single and the title track, "Pain Killer", released to country radio on August 24, 2015.

In February 2016, they appeared on "Take Me Down", a track on Down to My Last Bad Habit, the fourteenth album by Vince Gill.

They headlined the launch party in 2015 where they announced the full line-up, revealing they would be supporting Underwood along with Hunt and Maddie & Tae.

[21] In July, they appeared on the 2000–2005 episode of ABC's Greatest Hits where they performed covers by Alicia Keys, Oasis and Sheryl Crow.

The song's music video, directed by Reid Long and Becky Fluke, was released November 1, 2016.

Little Big Town announced a six-date UK tour supported by Seth Ennis beginning on September 28 and concluding in London on October 5[23] before revealing that Kacey Musgraves and Midland would support them on the American leg of The Breakers Tour beginning in February 2018.

The group then released "The Daughters" on April 5, 2019 as the first single from their ninth album Nightfall, which the band produced themselves.

The band embarked on a 30-date theatre tour of the same name with supporting act Caitlyn Smith, beginning with a show at New York City's Carnegie Hall the day before the album release.

Also in March, the group announced on social media that they would be collaborating with "lifelong friends" Sugarland at the 2024 CMT Music Awards.

[30] They announced on CMT Hot 20 Countdown on March 30, that they were in the process of recording a Christmas album, with an expected 2024 release.