Behind Little Big Town's Biggest Hits: Funny & Heartfelt Stories From The Country Group's Career-Defining Singles
Little Big Town

Photo: Blair Getz Mezibov


Behind Little Big Town's Biggest Hits: Funny & Heartfelt Stories From The Country Group's Career-Defining Singles

Little Big Town's Phillip Sweet and Jimi Westbrook commemorate the band's 20 years together by taking a look back at hits like "Pontoon" and "Girl Crush," as well as songs from their 10th studio album, 'Mr. Sun.'

GRAMMYs/Sep 23, 2022 - 05:13 pm

This year marks 20 years since country foursome Little Big Town released their debut album. And almost more impressively, the band is still composed of original members: Karen Fairchild, Kimberly Schlapman, Phillip Sweet, and Jimi Westbrook.

The quartet has created a legacy in their two decades together, releasing soulful ballads and jovial party starters that have helped the three-time GRAMMY winners become one of the most critically acclaimed country groups of their generation. Along the way, they've forged a familial bond that Westbrook and Sweet insist hasn't wavered. Their secret? "Lots of whiskey," Westbrook jokes. 

The more serious answer, though, is that they have created an environment of love and respect among the band. "The number one thing is us just trying to respect everyone's lives, we love each other and respect each other," Westbrook adds. "And we try to take care of each other the best we can. It's not perfect, but we try really hard." 

Little Big Town's 20-year anniversary was marked by the release of their 10th studio album, Mr. Sun. The album is a representation of both how they've evolved as a group, and the extensive time they've spent developing their sound. "We keep growing and evolving. We know who we are. We get inspired and excited about learning, about creating new things that we haven't done before," Westbrook says. "I feel like we're just scratching the surface of what we can do."

Just after Mr. Sun's arrival, sat down with Westbrook and Sweet over Zoom to look back at some of their biggest hits and get better acquainted with some tunes from their latest set.

"Little White Church," The Reason Why (2010)

Westbrook: We knew that we loved it. It felt fun. And it just had a great attitude and spirit to it. So I think we had high hopes for it, but you never know. I just remember the whole writing process of that back in the day, when we were working with Wayne Kirkpatrick, who was such a godsend in our career and early on. I remember writing it that day, [and] it being a lot of fun. We wrote it pretty quickly and then headed to a barbecue joint to celebrate. We always celebrate with food. [Laughs]

[For the video] I just remember that we were out in the woods. A ways out there by that weird spooky ghost story. That was the weirdest weekend. I lost my treasured 1932 Gibson guitar.

Sweet: Also, I remember us walking forever. It was a lot of walking and there was a camera guy that was following us and had to run backwards as he was filming the whole thing. And I think he had had too much to drink the night before. That didn't end well.

"Boondocks," The Road to Here (2005)

Westbrook: We were working with Wayne Kirkpatrick, like Jimi had mentioned earlier, who is just a beautiful human. He was a godsend to our life. We actually were working on another song called "Bones" that is on the same record. Those two songs kind of burst together. "Bones" and "Boondocks'' became something that were the cornerstones for that particular record.

We were talking about how they told us we were a put-together band and we were like, "No, we're, we're not. We're who we are." We had to speak from where we came from, and that's where "Boondocks" came from.

Sweet: There's nothing like playing that song. It's still my favorite thing. No matter where we are. It's definitely fun going home and I mean, I can't help but think of that. Especially when we have friends in the audience, like people I grew up with. You can't help but feel that connection, and it gives you a sense of pride. You feel like they know your story. And it's just so much fun every night. The reaction is so heartfelt from the crowd with that one as well — man, it'll lift you.

Westbrook: We performed with Lindsey Buckingham in 2006, on CMT crossroads. And he had something really unique to say about it. He was like, "it doesn't matter where you're from. This song just resonates with where you came from." And that's what we intended when we were writing it. 

"Pontoon," Tornado (2012)

Westbrook: I got an email from a friend saying "hey, listen to this song," and it kind of passed by for a little while. Then we went back later and listened to it again. And it really struck a chord. It's just such a quirky cool song. The groove to it is so good. That's what we loved, that swagger that it had in the groove. People really grabbed a hold of it when it came out.

Sweet: There's so much joy in that song. When we heard it, that's what we felt from it. It was instant. It had a vibe, it had a quirkiness to it that we loved. 

Westbrook: It definitely goes over well in festivals — summertime, everybody hanging out with drinks in their hand. A lot of times we will start the shows off with that, because [with] that lick, immediately everybody knows what it is.

"Day Drinking," Pain Killer (2014)

Sweet: That was me and Philip and Karen writing with Troy Verges and Barry Dean. That was just one of those great days hanging out with your friends. Troy brought his mando in that day and started the vibe off with that lick. We began day drinking, because we felt it was only appropriate.

"Girl Crush," Pain Killer (2014)

Westbrook: We knew from the beginning that there were interpretations, you know, at country radio, that kind of caused a little stir. And I love it. That's the beauty of music — it's people's stories. And those stories are interpreted differently in all kinds of ways.

I'm just proud of that song. That was such a catapulting moment for our band. That song is so special, and it does resonate deeply with people, and we're grateful for that, for sure.

Sweet: It was just nice to — I mean, in a weird way — to stir it up. It got people thinking, it got people moving, and differently than any other song we'd ever put out before. So, for that reason, I really am grateful as well.

We were lucky — the girls in our band went to write with <a href="">[Lori McKenna, Hillary Lindsey and Liz Rose, aka the Love Junkies] literally the day after they wrote that song. And they were saying in their session, "play something you just wrote" and that's what they played. 

Westbrook: Karen and Kimberly put that one on lockdown instantly. Like, "you can't play that for anybody else."

It was very intentional to make the track feel skeletal and haunting and, like, empty, because that's what your emotion would feel. And that was definitely the goal.

"Better Man," The Breaker (2016)

Sweet: We've known Taylor Swift for a long time, since she was just in the beginning in the business. And we would do label showcases together when she was really young, and we recognized the poise she had. So we always stayed connected and have always been friends. She had our emails and such.

She sent me an email and said, "Hey, I have the song. I have the demo. I just thought about your harmonies when I was writing it. And so check it out. No pressure." 

That was 2016. We were touring with Luke Bryan and we were making a record with Pharrell Williams [2016's Wanderlust]. I played it for the guys on tour and we were all like, "Holy smokes, man, this is a really good song," and I [knew I] needed to record it. I am just thankful she sent it to us.

"Mr. Sun," Mr. Sun (2022)

Westbrook: Sarah Buxton sent us that song, and from the first time we heard it, it has such a vibe to it. Another really classic melody. I love a good melancholy song. And that's what "Mr. Sun" feels like. Because you think with it being "Mr. Sun," it's going to be some bright shiny song, but it's a little blue.

"Rich Man," Mr. Sun (2022)

Sweet: Jimi wrote this song. I've been hearing this song in the dressing rooms and backstage for about 10 years. He said it wasn't really quite finished. We actually attempted to record this several years back, but it was one of those that was in the ether. Then Jimi said he finished it. And I said, "Man, that's just beautiful."

We were playing new music for some friends and they were like "play something we haven't heard." We played them "Rich Man," and their reaction was so authentic and visceral.

We were done with the record. And then the fact that we went in there and finished the album with "Rich Man" was just perfect. It was like the perfect little piece to the puzzle that we didn't even know [we needed]. It just made it feel so beautiful. It was perfect for this record.

Westbrook: It's one that it just kept hanging around. I would always come back to it, and then, maybe a year or so ago, finally felt like I wrapped it up like I wanted to. I wasn't even sure that anybody would even hear it. It was kind of my own. It's my own story in my heart for my family. But it's really cool that it found its way on the record.

"Three Whiskeys and the Truth," Mr. Sun (2022)

Sweet: Karen, Kimberly and Lori McKenna, Hillary Lindsey and Liz Rose, they get together and they didn't invite the boys. But they wrote this together and it's just so beautiful. I think it's just one of the most beautiful melodies.

Westbrook: Haunting as well. You feel that loneliness.

Sweet: Kimberly always says this in interviews — when they get together, like the girls and the Love Junkies, it's a safe place. It's a place where you can just speak your heart, your emotions. And they do that. And man, what beautiful things come out of that room.

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2018 GRAMMYs: Who's Performing?

Cardi B

Photo: Thaddaeus McAdams/


2018 GRAMMYs: Who's Performing?

Find out which of your favorite artists are performing on the 60th GRAMMY Awards on Sunday, Jan. 28

GRAMMYs/Jan 26, 2018 - 06:30 pm

The 60th GRAMMY Awards celebration in New York is quickly approaching. From rolling out the red carpet to tuning the guitars and adjusting the lights at Madison Square Garden, the Recording Academy is getting ready for the big milestone installment of Music's Biggest Night. But how about the performers?

Spanning multiple genres, including pop, rock, hip-hop, R&B, country, and more, this year's lineup of GRAMMY performers — many of them current nominees or past winners — will make for three-and-a-half hours of must-see television.

Without further ado, here is the list of performers for the 60th GRAMMYs.

Hosted by James Corden, the 60th GRAMMY Awards will take place at Madison Square Garden in New York on Jan. 28, airing live on CBS from 7:30–11 p.m. ET/4:30–8 p.m. PT.

'2016 GRAMMY Nominees' album now available


'2016 GRAMMY Nominees' album now available

Collection features 21 hits from Alabama Shakes, Kendrick Lamar, Little Big Town, Maroon 5, Chris Stapleton, Taylor Swift, The Weeknd, and more

GRAMMYs/May 15, 2017 - 01:36 pm

The 2016 GRAMMY Nominees album is now in stores and available via digital retailers. Released by The Recording Academy's GRAMMY Recordings and Republic Records, the 22nd installment of the best-selling series features 21 chart-topping hits from a diverse array of this year's GRAMMY-nominated artists and songwriters. A portion of the proceeds from album sales will benefit the year-round efforts of the GRAMMY Foundation and MusiCares.

The album includes artists and songs in the Record Of The Year, Album Of The Year, Song Of The Year, Best Pop Duo/Group Performance, and Best Country Solo Performance categories. Artists featured on the collection include Alabama Shakes, Cam, D'Angelo And The Vanguard, Florence & The Machine, Wiz Khalifa, Kendrick Lamar, Little Big Town, Maroon 5, Mark Ronson, Ed Sheeran, Chris Stapleton, Taylor Swift, The Weeknd, Carrie Underwood, Keith Urban, and Lee Ann Womack, as well as Best New Artist nominees Courtney Barnett, James Bay, Sam Hunt, Tori Kelly, and Meghan Trainor.

Order the 2016 GRAMMY Nominees Album

"The 2016 GRAMMY Nominees album represents some of the finest songs and talented artists that make up this year's remarkable nominees," said Neil Portnow, President/CEO of The Recording Academy. "We thank Republic Records for collaborating with us on this project, which also provides much needed support for the invaluable programs and initiatives our charities produce year-round. We look forward to another successful GRAMMY compilation."

"It's an honor to partner with the Recording Academy for the 2016 GRAMMY Nominees album," says Republic Records Founder/President Avery Lipman. "It's a very special project that captures the year through showcasing its biggest and best songs and simultaneously benefits some very important causes."

The 58th Annual GRAMMY Awards will broadcast live on CBS on Feb. 15 at 8 p.m. ET/5 p.m. PT. For updates and breaking news, visit The Recording Academy's social networks on Twitter and Facebook.

Where Do You Keep Your GRAMMY: Jimi Westbrook Of Little Big Town

Jimi Westbrook 


Where Do You Keep Your GRAMMY: Jimi Westbrook Of Little Big Town

The Where Do You Keep Your GRAMMY series by the Recording Academy is back with Little Big Town's Jimi Westbrook

GRAMMYs/Aug 29, 2019 - 04:59 am

Little Big Town's Jimi Westbrook remembers the time he almost quit music. "Really I cut my teeth singing gospel music when I was a kid," he told the Recording Academy about growing up in a musical family. "I sang my first solo in church when I was 12 and that was it I was done." 

That moment definitely was not the singer/songwriter's last with music. Years later Westbrook is a three-time GRAMMY winner, including for Best Country Duo/Group Performance during the 2010 GRAMMY Awards. In the first episode of the latest installment of Where Do You Keep Your GRAMMY, Westbrook let's us in on the exact room his golden gramophones are dispalyed—slight spoiler: they're in the same house GRAMMY winner Tammy Wynette  used to live in. 

Despite his success in what can be a tough industry, Westbrook stays thankful to create. "Because of the journey we've been on, we're just always really grateful to be able to still be making music and to be inspired still," he said. 

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Bruno Mars, Chris Stapleton, Kendrick Lamar: 14 Milestones At The 60th GRAMMYs

Chris Stapleton

Photo: Michael Loccisano/Getty Images


Bruno Mars, Chris Stapleton, Kendrick Lamar: 14 Milestones At The 60th GRAMMYs

Mars joins rare company, Stapleton makes Best Country Album history, Cara claims a first for the Great White North, and more

GRAMMYs/Jan 29, 2018 - 09:54 pm

Now that you've read all the major storylines about Music's Biggest Night, find out what history was made in New York on Jan. 28. Here are 14 records that were set at the 60th GRAMMY Awards.

1. Bruno Mars' Sweeps Three Big Four Categories

Bruno Mars swept the awards for Record, Album and Song Of The Year. He's the first male artist to sweep these three awards in one year since Eric Clapton did it 25 years ago.

2. Mars Captures Record, Song Of The Year

Mars is the first artist to win Record and Song Of The Year in the same year with different songs since Carole King achieved the feat 46 years ago. Mars took Record Of The Year with "24K Magic" and Song Of The Year with "That's What I Like." King won Record Of The Year with "It's Too Late" and Song Of The Year with "You've Got A Friend."

3. "That's What I Like": 8 Songwriters Recognized

"That's What I Like," with eight credited songwriters, set a new record as the Song Of The Year winner with the most co-writers. The old record, shared by seven songs, was four co-writers.

4. Alessia Cara: Canada's Best New Artist

Brampton, Ontario, native Alessia Cara won Best New Artist. She's the first artist who was born in Canada to win in this category.

5. Kendrick Lamar Sweeps The Rap Categories (Again)

Kendrick Lamar swept all four awards in the Rap Field. He also swept all four rap awards two years ago. He's the first artist to take home all of the rap awards more than once. Eminem swept the 2000 rap awards (when there were three). Kanye West swept the 2011 awards (when there were four).

6. Kraftwerk's First

Kraftwerk won Best Dance/Electronic Album for 3-D The Catalogue. This is Kraftwerk's first GRAMMY win, though the group received a Lifetime Achievement Award from the Recording Academy in 2014.

7. The Weeknd Doubles Up On Best Urban Contemporary Album

The Weeknd's Starboy took Best Urban Contemporary Album. The Weeknd won in this category two years ago for Beauty Behind The Madness. He's the first artist to win twice in the category since it was added in 2012.

8. Little Big Town's Best Country Duo/Group Performance Triple Play

Little Big Town won Best Country Duo/Group Performance for "Better Man." It's the quartet's third win in this category, which is more than any other duo or group since the category was streamlined in 2011. The group won for "Pontoon" (2012) and "Girl Crush" (2015).

9. Chris Stapleton Wins Second Best Country Album

Chris Stapleton's From A Room: Volume 1 won Best Country Album. He's the first male solo artist to win twice in this category since the category was re-introduced in 1994.

10. Shakira's Best Latin Pop Album Mark

Shakira took Best Latin Pop Album for El Dorado. The Colombian superstar is the first female artist to win twice in this category (which dates to 1983). She won 17 years ago for MTV Unplugged.

11. The Rolling Stones Roll With Blues Win

The Rolling Stones took Best Traditional Blues Album for Blue & Lonesome. The legendary band took the 1994 award for Best Rock Album for Voodoo Lounge. They are the first artists to win in both of these categories.

12. La La Land Soundtrack Doubles Up

La La Land won both Best Compilation Soundtrack For Visual Media and Best Score Soundtrack For Visual Media. La La Land is the first film to win in both of these categories since Ray took both awards for 2005.

13. Greg Kurstin Joins Elite Producer Company

Greg Kurstin took Producer of the Year, Non-Classical for the second straight year. He's the first producer to win two years in a row in this category since Babyface won three years running from 1995-1997.

14. Kendrick Lamar Joins With Best Music Video Win

Lamar took Best Music Video for "Humble." He won in this category two years ago for "Bad Blood," a collaboration with Taylor Swift. Lamar is the first rapper to win twice in this category. (Johnny Cash, Peter Gabriel, Janet Jackson and Michael Jackson are also two-time winners in this category.)

(Paul Grein is a veteran music journalist and historian whose work appears regularly at and

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