The Best Little Big Town Songs: 20 Country Essentials
These tune range from feel-good drinking songs to broken-hearted ballads to everything in between.
The roots of Little Big Town‘s signature soaring harmonies run decades deep – more decades, in fact, than encompass the band’s many years recording on Music Row. Karen Fairchild and Kimberly Schlapman first met in 1987, when the Georgia natives were both attending Samford University in Alabama. Both separately moved to Nashville and reconnected in Music City almost a decade later, where they decided that they wanted to find some men to sing with to flesh out those harmonies.
The harmonies have remained constant since before the release of their self-titled debut in 2002. “Our label was like, you have to pick a lead singer, and we were pretty strong about, ‘No, we don’t. That’s not what we’re going to do,’” Schlapman told Rolling Stone in 2020, explaining some of the stops and starts they experienced over the next decade. Their commitment to singing together started to pay off in earnest once they joined forces with producer Jay Joyce for their 2012 album Tornado and had the major hits they’d long since been angling for, translating Fleetwood Mac superfandom and backcountry bonafides into something Music Row hadn’t ever seen before.
Combining radio sensitivity with a decidedly unNashvillian proclivity for risk-taking, an ear for tradition with tight ties to some of modern country’s best and most prolific songwriters, Little Big Town has made their own way in a format that prizes conformity. Here are 20 of their best songs, ranging from feel-good drinking songs to broken-hearted ballads and everything in between.
Order Little Big Town’s Greatest Hits.
Life In A Northern Town – Live (2008)
This one-off live collaboration with Sugarland and Jake Owen was an unlikely success, reaching No. 28 on Billboard’s country chart off of unsolicited airplay and getting nominated for a bevy of awards. Originally a hit by the British band The Dream Academy, “Life In A Northern Town” was composed as an elegy for Nick Drake – perhaps a slightly unlikely marriage with the Music Row-bred trio of collaborators, but one that clearly worked as evidenced by the epic-scaled track.
Hell Yeah (2022)
Another entry in Little Big Town’s catalog of sunshine-y, feel-good songs, this track has that bright vibe with a twist: The narrator (on this one, Philip Sweet) is still sad about lost love, but he’s putting on a brave face for the sake of the party. There’s whistling, there are harmonies, there are grooves – and just enough pathos to make it country.
Nightfall (2020)
Disco country – and Kacey Musgraves – fans would do well to listen to this lightly groovy track, co-produced by Danial Tashian and Ian Fitchuk of Musgraves and Golden Hour fame as well as the quartet themselves. Nestled in the understated album track is a totally radio-ready hook: “You and I fall, baby, when the night falls.” More a feature for Karen Fairchild than the ensemble, it’s nevertheless a lesser-known gem in their catalog.
Sober (2012)
The Love Junkies – Liz Rose, Lori McKenna and Hillary Lindsey – went deep on their favorite topic on this track, which features Kimberly Schlapman singing lead. It may not have been a radio hit, but the upbeat song shows Little Big Town at their sweetest, supported by a lush, understated arrangement (the Hammond B-3 is a nice touch). Love is the only drug they’re interested in!
When Someone Stops Loving You (2017)
Jimi Westbrook takes the lead on this heart-wrenching ballad, which details all the mundane ways that life goes on even when it seems like it won’t. It may not have caught on at country radio, but the gentle waltz, co-written by Hillary Lindsey and Lori McKenna, shows the quartet’s soaring vocals to great effect. The Breaker was their return to straight country after collaborating with pop hitmaker Pharrell, and that’s evident few places more than this plainspoken break-up tune.
Shut Up Train (2010)
Buried in The Reason Why is this Hillary Lindsey, Chris Tompkins (“Before He Cheats”) and Luke Laird-penned gem. The song is an intimate one, featuring moments of Karen Fairchild singing alone over acoustic guitar about her broken heart (it is a country song, after all). The stripped-down arrangement is an ideal showcase for the quartet’s easy precision, and the song is familiar while still being different enough to hold your attention.
Why Oh, Why (2010)
There’s a little bit of Sheryl Crow-style ’90s rock to this one, which the group co-wrote with Jonathan Singleton and a pre-megafame Chris Stapleton. Despite being an album cut, it has the pomp and heft of a radio-ready single, complete with catchy hook, soaring harmonies and guitar solos. It’s a change of pace from some of the more bluegrass-inflected sounds of their early albums, and one that anticipates the radio hits to come.
Tornado (2012)
The second Little Big Town single produced by Jay Joyce, “Tornado” – like “Pontoon” – showed a glossier, more pop-crossover-ready side of the quartet. There’s synth effects and drum machines here, but the relatively minimal arrangement keeps the harmonies front and center. Karen Fairchild does the heavy lifting on this stormy tune, putting a new spin on “hell hath no fury” while never losing the song’s radio-ready groove.
Quit Breaking Up With Me (2014)
This dry, twangy tune allowed the women of Little Big Town to take center stage, dressing down some n’er-do-well with more than a little bit of humor and exaggeration. An album cut, it nevertheless has an all-star cast of songwriters, including Natalie Hemby, Shane McAnally and the late busbee. A little more rough-and-tumble than most Little Big Town songs, its 90s pop grit suits Fairchild and Schlapman to a T.
I’m With The Band (2007)
In Nashville, a town of solo artists, Little Big Town must have felt compelled to stake their claim as an ensemble. Enter this slow-built, harmony-rich ode to the musician’s life, a modern-day “On The Road Again” sung by a quartet who had certainly already spent their share of time moving from gig to gig. The song’s expansion is a satisfying one; by the time they reach the fireworks, listeners are primed for them.
Wine, Beer, Whiskey (2020)
How often do you hear trumpet on a country album? Well, for all the fans who pushed this Little Big Town single to platinum certification twice over (without much help from country radio), the answer is probably pretty often. Yet the nominally classic drinking song is another unconventional choice from a band who’s made a career of them, with its almost mariachi-esque trumpet lines and deep pop groove; their harmonies are pressed into a rowdy sing-a-long rather than showcased, encouraging listeners to join in.
Your Side Of The Bed (2012)
This one is all about the vocals – when the harmonies explode in the chorus, listeners can get a full sense of just what makes Little Big Town so special. In the song’s more intimate moments, though, which feature Karen Fairchild and Jimi Westbrook, it’s hard to remember that you’re hearing a song that was released as a single and ultimately went platinum because they feel so much like acoustic one-offs. That wide range, within the span of one evocative song, shows just what the group is capable of.
Good As Gone (2005)
The opening song on one of their two records with Clint Black’s Equity Music Group, “Good As Gone” finds the quartet operating at their most traditional, with layers of acoustic instruments supporting their tight harmonies. It might be hard to imagine the quartet as hardscrabble upstarts, but here their outsider status is audible in a good way. A modest chart hit, in retrospect the song shows just how wide the group’s range is.
Little White Church (2010)
Karen Fairchild shows off her sassier side on this boot-stomping anthem, singing to some hapless man who’s been refusing to make an honest woman out of her. The bouncy track reached No. 6 on Billboard’s country chart, with handclaps and a rock edge balancing the song’s almost Appalachian, traditional-sounding harmonies. Certainly different than many of its peers on country radio, the song, which the quartet wrote together, still proved to be their first hit for Capitol Nashville.
Day Drinking (2014)
Having found their summery sweet spot with their first major hit “Pontoon,” Little Big Town tapped a similar well (and similar collaborators, in co-writer Barry Dean and producer Jay Joyce) with this lighthearted ode to imbibing while the sun’s still up. With its rockish edge and its drumline/whistled interludes, this isn’t your average tailgate playlist song – but it still fit well enough at country radio to reach No. 2 on Billboard’s Country Airplay chart.
Next To You (2020)
Not released as a single, this romantic, cinematic duet nevertheless scraped the bottom of the country chart – showing how Little Big Town fans appreciate the band’s moodier side just as much as their drinking songs. Jimi Westbrook and Karen Fairchild narrate this love song, which is confessional, confrontational, and affectionate in turns, just like real-life partnership. It starts casual and intimate before building to an arena-ready conclusion (and spotlight for the group’s harmonies).
Boondocks (2005)
Little Big Town’s first top-ten hit on the country charts, “Boondocks” announced that they had arrived with an abundance of bluegrass-tinged twang and, of course, crisp harmonies. The song, an ode to rural living, was written by the quartet. The reason it has remained one of the band’s favored closers, though, is because of the fiery vocal breakdown at its conclusion – showing the technical mastery and deep country feeling of this idiosyncratic group.
Better Man (2016)
It’s not everyday that Taylor Swift writes a song for somebody who’s not Taylor Swift. So when Swift sent Little Big Town this castoff from Red with the suggestion that it would sound great with their harmonies, they embraced it. A vocal showcase for Karen Fairchild as much as for the ensemble’s seamless collaboration, the power ballad became one of the biggest hits of their career, winning both a Grammy and a CMA award while topping the country charts. Swift eventually released the heartbreak tune herself on Red (Taylor’s Version), but not before it became a Little Big Town signature.
Pontoon (2012)
A decade after Little Big Town made it to Nashville, they finally got their first No. 1 song on the country charts with this lazy summer day anthem. The song, penned by Music City stalwarts Natalie Hemby, Luke Laird, and Barry Dean, blends a twangy mandolin riff, an unlikely source of inspiration (“Pontoon” comes from someone mishearing the name of “Fine Tune” by Miranda Lambert) and a healthy dose of innuendo, “out here in the open.” The warm weather classic earned the group both their first Grammy award, for Best Country Duo/Group Performance, and their first CMA awards for Best Vocal Group and SIngle Of The Year.
Girl Crush (2014)
An outside-the-box idea from some of the top songwriters in Nashville turned into a modern country classic in the hands of Little Big Town and specifically Karen Fairchild, who sings lead on this breathless tune. Lori McKenna, Liz Rose, and Hillary Lindsey penned this track, in which obsessive jealousy makes a woman fixate on her competition…but in a way that was more sexy than angry, and certainly more sexy than most of the songs on country radio’s playlists. Smart, unexpected and decidedly catchy, “Girl Crush” helped Little Big Town rack up hardware, going platinum six times over and sweeping the CMAs and Grammys (while even earning a nomination for Song of the Year). More importantly, though, it cemented their legacy as one of modern music row’s most successfully eclectic, risk-ready acts while paying off in a big way.
