The 10 Best Little Big Town Songs of All-Time

Little Big Town

In 1998, Karen Fairchild, Kimberly Schlapman, Phillip Sweet, and Jimi Westbrook came together to form Little Big Town. Although they had the harmonies and the melodies from the start, it took them almost a decade to start enjoying any kind of success. Since then, there’s been no stopping them. Here, we take a look back at their career with our pick of the 10 best Little Big Town country music songs of all time.

10. Night Owl


Night Owl was never released as a single, but as Billboard notes, ever since their debut, Little Big Town has had a habit of including album cuts that are just as exceptional as any of their singles. Recorded as the closing track to their fifth studio album, Tornado, it’s a haunting track with the kind of call and answer harmonies that would put the Everly Brothers to shame. Fun fact – according to, the cooing chorus was created by the band singing into an echo chamber. “At the studio, there’s a little hole in the wall that you go through to the chamber, where there are microphones set up to catch the echo. We all got inside to sing the ‘who-o-oohs,'” Phillip Sweet explains.

9. Day Drinking


The band needed a corker to kick off their Pain Killer album, and they found one in the form of Day Drinking, a light, bright little number that as says, really does make you want to pop a top in the middle of the day. According to Karen Fairchild, the song was just as much of a blast to make as it is to listen to. “We didn’t know it really, but with ‘Day Drinking,’ we had a blast that day because we were drinking and writing songs. We left it alone, then a couple of weeks later, Barry Dean and Troy Verges sent us a souped-up work tape of what we had done. Then, we thought this is very fun and very cool,” she’s recalled to Billboard.

8. Sober


After the light and lively Day Drinking, we come crashing back to earth with the emotive Sober, a gorgeous number that showcases the song-crafting genius of the band. Kimberly Schlapman’s vocal performance is a rare treat, adding a soaring brilliance to the already stunning lyrics. Released in September 2013 as the fourth single from their fifth studio album, Tornado, it peaked at number 2 on the U.S. Billboard Bubbling Under Hot 100 Singles chart.

7. Better Man


If Taylor Swift decides to write a song for you, you know you’re going to be spending a few weeks in the charts. And wouldn’t you know it, that’s exactly what happened to Little Big Town in 2016 with Better Man. Released as the lead single from the group’s eighth studio album, The Breaker, it spent several weeks working its way up the charts until it eventually reached the top spot. The following year, it won Song of the Year at the 2017 CMA Awards and a Grammy Award for Best Country Duo/Group Performance.

6. Boondocks


Although Little Big Town formed in 1998, it would take several years and two failed record contracts before they finally started getting anywhere. Boondocks, the first single from their second studio album, The Road to Here, became their first Top 10 hit on the Billboard Hot Country Songs charts, peaking at No. 9 in June 2005. It also gave them their first taste of crossover success, achieving a No.46 chart position on the Billboard Hot 100. A fist-pumping ode to the joys of rural living, it still ranks as one of their most popular songs to this day.

5. I’m With The Band


I’m With The Band from Little Big Town’s third album, A Place to Land, may have peaked at a relatively disappointing No. 32 on the Billboard Hot Country Songs chart, but that’s less a reflection of the song than it is of the band’s status at the time. Three albums into their career, and country radio still hadn’t caught onto to their charms, resulting in little airplay and fewer sales than they deserved. Still, everyone got with the program eventually, and it’s thanks to songs like this that they did.

4. Pontoon


Most bands start winding down after 15 years together. Clearly, Little Big Town are cut from a very different cloth to most. Released in 2012 as the first single from their fifth studio album, Tornado. Pontoon earned the band their biggest ever hit, peaking at No. 1 on the Billboard Hot Country Songs chart and snagging the 2013 Grammy Award for Best Country Duo/Group Performance. An upbeat number about having a party while on a pontoon, it’s a blast, with Karen Fairchild delivering one of her best ever vocal performances.

3. Your Side Of The Bed


Named as one of the best Little Big Town songs of all time by Classic Rock History, Your Side Of The Bed tells the story of a couple who might live under the same roof, but who couldn’t be further apart if they tried. The fact it’s performed by husband and wife Karen Fairchild and Jimi Westbrook adds an extra layer of drama to an already emotional song.

2. Little White Church


In 2010, Little Big Town teamed up with Wayne Kirkpatrick for Little White Church, an energetic romp about a woman telling her other half that he can either put a ring on it or take a running jump. Karen Fairchild gives a rousing turn on lead vocals, with the rest of the group contributing some gorgeous harmonies and some very playful handclaps. The worst you can say about it is that it’s a little simplistic. The best you can say about it is that it’s one of the brightest, liveliest, and most seductive songs to have graced country radio in years.

1. Girl Crush


Lori McKenna, Hillary Lindsey, and Liz Rose have written some outstanding songs for Little Big Town over the years, but few match up to the glorious Girl Crush. Karen Fairchild’s vocals are astonishing, driving the song forward with so much passion and anguish, it’s almost exhausting to listen to (but in a good way). Released in 2015, it quickly established itself as one of the band’s highest-selling and most critically acclaimed singles of all time, peaking at No.1 on the US Hot Country Songs chart and No. 11 on the Billboard Hot 100. If that wasn’t enough, it also managed to snap up five music awards (including two Grammys) and become the second most played song of the year.

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