In the late 90s, the group signed to Mercury but did not release anything. They then moved over to Monument and released one self-titled debut album, from which only two low-charting singles were released before Monument closed its Nashville division.
Clint Black picked the group up in 2005 and signed them to his Equity label, where LBT scored a dark-horse Top 10 hit late in the year with "Boondocks", and another with its followup, "Bring It On Home", followed by the lesser hits "Good as Gone" and "A Little More You". The corresponding album, The Road to Here, was produced by songwriter Wayne Kirkpatrick, who gave them a more raw, earthy feel than their first album. These four singles boosted their album to platinum sales, and earned them ACM and MCA nominations, as well as a touring spot with Sugarland and Jake Owen.
2007's A Place to Land had its lead single "I'm with the Band" fizzle out at #32, followed promptly by the closure of Equity. Shortly afterward, a concert recording of them covering The Dream Academy's "Life in a Northern Town" on the Sugarland/Jake Owen tour also cracked Top 30, at which point Little Big Town announced that Capitol Records had picked them up. Capitol re-issued A Place to Land with several new tracks, and released two more singles from the project, but they were also unsuccessful.
"Little White Church" from 2010's The Reason Why got them a third Top 10 hit finally, but the follow-ups both failed to make Top 40, despite a second tour with Sugarland. Two years later, the band switched producers to Jay Joyce (Eric Church, Cage the Elephant), and finally got its first #1 hit with "Pontoon", the lead single to Tornado. This song also netted them their first-ever Grammy (for Best Country Duo/Group Performance), while the title track went on to become a #2 hit in 2013. After two lower-charting singles, Little Big Town launched its sixth album with "Day Drinking", followed by their biggest hit to date, "Girl Crush". A detour to pop territory in 2016 with the Pharrell Williams-produced Wanderlust was unsuccessful, so they returned to country in 2017 with The Breaker — led off by the Taylor Swift-penned "Better Man".
- Little Big Town (2002)
- The Road to Here (2005)
- A Place to Land (2007)
- The Reason Why (2010)
- Tornado (2012)
- Pain Killer (2014)
- Wanderlust (2016)
- The Breaker (2017)
- Bait-and-Switch Lesbians/Bi the Way: Played with in "Girl Crush", the woman is obsessing after another woman, only because she's jealous of the fact that the other woman has a man whom the narrator desires.
- Early-Bird Cameo: Back when they were signed to Mercury, they sang backing vocals on Collin Raye's Can't Back Down, and Sweet and Roads co-wrote a song for Sherrié Austin in 2001.
- Early Installment Weirdness: Their first album had much slicker, poppier production than their most famous works. Also, both of its singles had Kimberly and Philip singing lead, when the Equity albums relied more on rotating the lead vocal more evenly, and the Capitol albums more on Karen.
- Long Runner Lineup: Same four people since 1998.
- Love Is a Drug: "Sober":I love being in love
It's the best kind of drug
Drunk on the high
Leanin' on your shoulder
Sweet like wine as it gets older
When I die, I don't wanna go sober
Oh when I die, I don't wanna go sober
- Mondegreen: "Pontoon" came about as the result of this. Co-writers Luke Laird and Natalie Hemby wrote a song for Miranda Lambert called "Fine Tune"; a publisher later inquired about the song, but thought that it was called "Pontoon". After Hemby corrected him, the two thought that they actually should try writing a song called "Pontoon".
- Moral Guardians: "Girl Crush" supposedly caught a lot of heat in 2015 due to listeners misconstruing it as promoting lesbianism, but most of it was discovered to be manufactured by the label to generate interest in the song.
- New Sound Album: They released a pop album, Wanderlust, in 2016. It was produced by Justin Timberlake and Pharrell Williams.
- Record Producer: Songwriter Wayne Kirkpatrick, who is not often a producer, handled their second through fourth albums and helped them define their sound. Jay Joyce carried on in a similar fashion from Tornado onward.
- Solo Side Project: Karen sang duet vocals on Luke Bryan's late-2015 release "Home Alone Tonight".
- Vocal Tag Team: Karen usually gets the singles, but the other three members have carried at least one single each:
- Everyone in varying combinations: "Boondocks", "I'm with the Band", "Good Lord Willing", "Life in a Northern Town" (which also had Jake Owen and both members of Sugarland sharing the lead)
- Kimberly: "Sober"
- Kimberly/Philip: "Don't Waste My Time", "Everything Changes"
- Jimi: "A Little More You", "When Someone Stops Loving You"
- Karen/Jimi: "The Reason Why", "Your Side of the Bed"
- Philip: "Bring It On Home", "Kiss Goodbye"
- Woman Scorned: The subject of "Tornado", in which the female compares herself to a tornado.