Artist - Willie Nelson 3 

Graphic - The Best Sad Country Songs 

The Best Sad Country Songs

If you’re feeling particularly fed up today, don’t worry. You won’t be alone in feeling blue. We all have off days; those when it feels like a little black cloud is following us everywhere we go, making everything gloomy and miserable.

Life isn’t always blue skies and puppy dogs, and sometimes it’s a whole lot of hard work just getting through the day. But if we were happy 

 the time we wouldn’t need sad songs, and sad songs are some of the greatest songs in the whole world - especially in country. 

Sometimes the best thing to do is wallow in all that misery and make a day of it; sit under that rain cloud and just enjoy getting absolutely soaked. It’s like Dolly always says: “If you want the rainbow, you gotta put up with the rain”.

So sit back and indulge in the tearjerking tones of Holler’s Best Sad Country Songs playlist. Let Willie and Dolly take it from here. We can all try again tomorrow.

1. Blue Eyes Crying In the Rain - Willie Nelson

3. I'm So Lonesome I Could Cry - Hank Williams 

4. He Stopped Loving Her Today - George Jones 

8. Whiskey Lullaby - Brad Paisley, Alison Krauss

12. Rosewood Casket - Dolly Parton, Linda Ronstadt, Emmylou Harris 

13. I Fall To Pieces - Patsy Cline, The Jordanaires 

15. Dawn From Dover - Nancy Sinatra, Lee Hazlewood 

18. The Long Black Veil - Lefty Frizzell 

21. She Thinks His Name Was John - Reba McEntire 

22. Go Rest High On That Mountain - Vince Gill 

24. If We Were Vampires - Jason Isbell and the 400 Unit 

30. Waiting Around to Die - Townes Van Zandt 

31. Life Turned Her That Way - Ricky Van Shelton 

32. Heaven's Only Days Down the Road - Shelby Lynne 

33. The Last Word In Lonesome Is Me - Roger Miller 

36. The Little Girl - John Michael Montgomery, Alison Krauss, Dan Tyminski 

38. Every Time I Hear That Song - Brandi Carlile 

39. Holes In The Floor Of Heaven - Steve Wariner 

40. If Something Should Happen - Darryl Worley 

Subscribe and listen to Holler's The Best Sad Country Songs Playlist above.

A playlist of 40 of the best sad country songs from Holler, featuring Willie Nelson and Dolly Parton. 

Playlist

A selection of country music's finest tearjerkers 

It’s like Dolly always says: “If you want the rainbow, you gotta put up with the rain”

Sad Country Songs - A List of 40 of the Best | Holler 

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Singer/songwriter and multi-instrumentalist Allison Russell was born in Montreal, where music became an outlet to escape her troubled home. 

From that early interest, Russell joined the Canadian roots act Po'Girl in the early aughts. 

Eventually, she began collaborating with her future husband, Chicago-based singer/songwriter J.T. Nero, on his project mountains/forests until the pair eventually formed their own duo, Birds of Chicago, in 2012. 

They released several albums together until Birds of Chicago went on indefinite hiatus in 2021, as Russell turned her attention to her solo career with the release of her debut solo album 

Russell is also a member of Our Native Daughters, alongside Rhiannon Giddens, Amythyst Kiah and Leyla McCalla. The group released their debut album, 

Allison

Artist - Allison Russell 2

Amanda

Artist - Amanda Shires 2

Artist - Amanda Shires 1

Ashley Monroe began singing at a young age - even winning a talent contest at age 11. But it would take a few more years before she brought her talent to Nashville. 

Once she relocated to Music City, she landed a songwriting publishing deal that eventually led to a record deal with Sony Music. Her debut album 

 was ready to go, but her singles weren't charting as well as the label wanted, so they delayed and eventually pulled the plug altogether. 

 to digital retailers in 2009 - following it up with her self-titled EP the same year. Her emotionally driven, pop-country sound caught the attention of Warner Bros. Nashville, who signed Monroe and released her sophomore album 

 in 2013. Grand Ole Opry staple and legendary singer/songwriter Vince Gill produced it. 

, came out in 2015 and was nominated for Best Country Album at the Grammys. Three years later, after giving birth to her son, Monroe released her fourth album 

 in 2018. This time, Dave Cobb served as producer. 

Besides her solo work, Monroe is a member of the supergroup Pistol Annies with Miranda Lambert and Angaleena Presley. They released the albums 

 on 2018. The latter was nominated for Best Country Album at the Grammys. 

In 2021, Monroe released her fourth album 

Ashley

Artist - Ashley Monroe 1

Ashley McBryde didn't wait for the Nashville majors to back her talent. She self-released her first album in 2006, before moving to Music City to focus exclusively on writing and performing country music. 

In her first few years in Nashville, McBryde won the Country Showdown in 2009 and 2010. 

She continued touring behind her music, and eventually released the EP 

 in 2016. One year later, Warner Bros. Records in Nashville released her single 'A Little Dive Bar in Dahlonega'. 

McBryde co-wrote the song with Nicolette Hayford and Jesse Rice. It's about having the worst day but making the best of it. The song garnered critical attention, including from 

which named it as one of the 54 Best Songs of the Year. 

The single ended up on McBryde's 2018 debut studio album 

. Thanks to the popularity and critical success of the album, McBryde was named Female Vocalist of the Year at the ACMs and New Artist of the Year at the CMAs in 2019. Her debut album also earned a Best Country Album nomination at the Grammys. 

In 2020, she released her sophomore album 

. Once again, it was nominated for Best Country Album at the Grammys.

Artist - Ashley McBryde 1

Country music star Blake Shelton learned to play the guitar as a young boy and took that talent to Nashville at age 17. He worked in and around the music industry, before eventually landing a record deal in 2001. 

Shelton released his first single 'Austin' that same year. It went to the top spot on 

's Hot Country Songs chart (formerly known as Hot Country Singles & Tracks). 

He released his self-titled debut that year as well, beginning a steady output of LPs that have accumulated to make him one of the most successful male country artists of his time. They include 2003's 

In between those albums, Shelton also released the 2012 Christmas album 

, Shelton accrued 17 consecutive number one country singles. 

Thanks to his impressive catalogue, Shelton was inducted into the Grand Ole Opry in 2010. The honor followed a serious number of industry accolades, including CMA, ACM and CMT Awards. Shelton won Male Vocalist of the Year at the CMAs five consecutive years, between 2010 and 2014. 

Since 2011, Shelton has served as a coach on NBC's 

. Thanks to his presence on the musical competition series as well as his music, Shelton made the cover of 

's Sexiest Man Alive issue in 2017. He became the first country music artist to achieve that title. 

Blake

Artist - Blake Shelton

Artist - Bob Dylan

Across an incredible catalogue of work, Americana singer/songwriter Brandi Carlile has written perceiving and perceptive songs. The Pacific Northwest native learned how to sing and play guitar and piano during her early years, translating those talents into a remarkable storytelling ability. 

Carlile released her self-titled debut album in 2006. But it was her 2007 sophomore album The Story — produced by T Bone Burnett — that began garnering more attention for her music. She turned to famed producer Rick Rubin for her 2009 album Give Up the Ghost.

Both her 2016 and 2019 albums – The Firewatcher’s Daughter and By the Way, I Forgive You – won Grammys for Best Americana Album. 

Outside of working on her own music, Carlile co-produced Tanya Tucker’s 2019 album While I’m Livin’ with Shooter Jennings. The moment was milestone, as Carlile had taught herself to sing by listening to Tucker and Patsy Cline.

She also performs as part of the supergroup The Highwomen, alongside Maren Morris, Amanda Shires and Natalie Hemby. Their song ‘Crowded Table’ won the 2020 Grammy for Best Country Song. In 2021, Carlile released her autobiography Broken Horses: A Memoir.

Carlile is out and proud. In 2008, she co-founded the Looking Out Foundation with the Hanseroth Twins, who she used to play in Seattle with as a young performer. It addresses multiple needs, and $1 from every concert ticket Carlile sells goes back to the non-profit. 

Brandi

Artist - Brandi Carlile 3

Brandy

Artist - Brandy Clark 2

Artist - Brandy Clark 1

Given that Breland grew up surrounded by gospel music — thanks to his minister parents — it would make sense that his career might trend in that direction. But instead he's developed a country sound that integrates elements of trap, hip-hop R&B and soul. Critics call it "country-trap", but Breland calls it "cross country". 

After growing up in New Jersey, Breland attended Georgetown University, where he performed in an a cappella group and worked on writing his own music. He moved to Atlanta after graduating and learned how to engineer, sharing the tracks he produced on social media. 

Those platforms helped Breland amass a following and a serious number of streams, all of which led to a record deal with Bad Realm Records/Atlantic Records. 

. His sound has garnered support from major country artists. Breland partnered with Mickey Guyton for his single 'Cross Country' and with Keith Urban on his single 'Throw It Back'. 

Breland

Artist - Breland 

Brett Eldredge may have grown up singing jazzy vocal numbers by the likes of Frank Sinatra and other iconic crooners, but it’s country where he’s found his home.

Eldredge released his debut album Bring You Back in 2013, introducing listeners to his soulful baritone voice and earning three big hits. The singles ‘Don’t Ya’, ‘Mean to Me’, and ‘Beat of the Music’ topped the Country Airplay charts. 

Those early commercial successes translated into a CMA Award for New Artist of the Year in 2014.

His sophomore album, named after his home state of Illinois, came in 2015, and Eldredge followed it with the Christmas album Glow one year later. 

But Eldredge hasn’t left his past behind entirely. He regularly covers Sinatra and even told Rolling Stone that he’d love to record a covers album one day.

Eldredge’s fifth studio album, Sunday Drive, was released in 2020.

Brett

Artist - Brett Eldredge 1

Baltimore-born singer/songwriter Brittney Spencer grew up singing in church choir, a gospel foundation that has leant itself to the country music she's since crafted. 

Although she studied classical voice as a young girl, in the hopes of attending George Washington Carver Center for Arts and Technology, it was ultimately country that most entranced her. At age 15, a friend introduced her to the genre.  

Spencer moved to Nashville in 2013, where she began singing backing vocals for Carrie Underwood and Christopher Cross, among other artists. All the while, though, she kept writing her own songs and in 2020 she released her debut EP 

Her music garnered praise and led to her Grand Ole Opry debut in May 2021. Spencer has also been named to CMT’s Next Women of Country class of 2021. 

Brittney

Artist - Brittney Spencer 3

The country duo Brothers Osborne – John (guitar) and T.J. (vocals) – grew up playing music with their family, but that almost didn’t translate to a professional career. 

They both landed in Nashville after graduating high school two years apart, but they pursued other projects in an attempt to develop solo careers. But their power ultimately lay in playing together, and eventually they began performing as a duo at some of Nashville’s smaller venues. 

That push drew the attention of EMI Records Nashville, which signed John and T.J. in 2012. With that opportunity, they continued performing, releasing singles and recording a self-titled EP in 2014, all of which lead to their debut album Pawn Shop in 2016 and two big accolades. Thanks to John’s electrifying guitar playing and T.J.’s growling baritone, Brothers Osborne was named Vocal Duo of the Year by the Academy of Country Music and the Country Music Association in 2016 and 2017.

Brothers Osborne followed their early critical success with 2018’s Port Saint Joe and 2020’s Skeletons, albums which showcased their penchant for blurring country with southern rock. 

In 2021, T.J. made headlines when he opened up to TIME Magazine about being gay. The announcement made him the first country artist signed to a major label to come out. 

Brothers Osborne

Artist - Brothers Osborne 1

Artist - Cam 6

Artist - Cam 7 

Artist - Cam 1 

Artist - Cam 4 

Artist - Cam 2 

Artist - Cam 3 

Album - Cam - The Otherside 

Carly 

Artist - Carly Pearce 1 

Carrie Underwood’s career might’ve started much earlier had things gone a different way. At age 14, she auditioned for Capitol Records in Nashville. The label was going to offer her a contract, but that deal fell through when they changed management.

Underwood returned to Oklahoma, finished high school and later graduated from Northeastern State University. Things took a turn for the singer in 2004, when she auditioned for American Idol. Despite a shy start on the show, she would go on to become the season four winner, with a powerful voice that enraptured audiences around the globe.

But not every American Idol winner goes on to make such a big splash. Underwood’s first official single ‘Inside Your Heaven’ landed at the top spot on Billboard’s Hot 100 list, making her the first country artist to debut at number one. 

She released her debut album Some Hearts in 2005 and by 2006 she’d earned the Top Female Vocalist of the Year at the CMAs and ACM Awards. Her second album Carnival Ride arrived in 2007, the same year she won Best New Artist at the Grammys. 

Given Underwood’s popularity in country music, she began co-hosting the CMA Awards with country singer Brad Paisley, serving that role for 12 years. As she continued releasing new music, Underwood also starred as Maria in NBC’s live version of The Sound of Music.

When she released her fifth studio album Storyteller in 2015, Underwood became the first country artist who debuted all of her albums at either the first or second spot on the Billboard 200. 

In addition to her commercial success, which includes major headlining tours, and ongoing critical acclaim, Underwood has won several Grammys for her music. In 2020, she published her first book, Find Your Path, and released her eighth studio album My Savior in 2021.

Head here for a definitive list of Carrie Underwood's best songs.

Carrie

Artist - Carrie Underwood 3

Carrie Underwood Features and Playlists from Holler

Charley Pride taught himself to play guitar as a young boy, but his heart seemed set on baseball. Pride pitched for various teams in the Negro League, in the 1950s, before being traded to the minors. 

Eventually, he ended up playing for a semipro team in Helena, Montana. That coach heard his singing ability and asked him to perform for a few minutes before each game in order to increase attendance. 

Pride cut a few demos at Sun Studios in Memphis, which ended up in the hands of RCA Records' Chet Atkins, who signed Pride, though publicizing him as a black artist singing country music remained a point of contention. 

Pride released a number of singles, but it was his third, "Just Between You and Me", that garnered him success. It reached the top ten on the Hot Country Songs chart in 1967 and was nominated for a Grammy. That same year, Pride became the second black artist to perform at the Grand Ole Opry - after DeFord Bailey. 

Pride's music continued charting, but it was his 1971 single "Kiss an Angel Good Mornin'" that became his biggest hit. It stayed at the top spot on the country charts for five weeks and even made it crossed over to the top-40 pop singles chart. 

In 1971, Pride was named Entertainer of the Year at the CMAs. 

Throughout the 1980s and 1990s, Pride continued touring and releasing hit singles. In 1994, he released his biography 

. In 1997, he had a tumor removed from his vocal cords, but he continued to sing and perform after the operation. 

Pride was eventually inducted into the Country Music Hall of Fame in 2000. He was also honored with the Willie Nelson Lifetime Achievement Award at the 2020 CMAs. Later that year, Pride passed away due to complications from COVID-19 in December. 

Charley

Artist - Charley Pride

Charley Crockett has an aura of myth about him. As the distant relative of American folk hero Davy Crockett, he's lived up to his ancestor's name, traveling all over the country and gathering its influences into what he describes as his 'Gulf + Western music', which blends traditional country, honky tonk, blues and soul.  

Crockett was born in 1984. He grew up in Texas, where he taught himself to play guitar and write songs without any formal training. He left home at 17, using music to support himself as he busked and played in New Orleans, New York, and across the U.S. 

His talents attracted attention from the music industry, including a two-year management deal with Sony Records, but that didn't pan out. Instead, he went to Northern California, where he worked on farms, before heading to France and Morocco. 

When he returned Stateside, Crockett self-released his debut album 

 in 2015. Over the next six years, he went on to release a total of ten albums. But it wasn't until the release of 2020's 

that he began attracting more national attention for his music.  

He followed that breakthrough with a tribute album in honor of James 'Slim' Hand called 

10 For Slim: Charley Crockett Sings James Hand, 

which he released in 2021. That same year, Crockett released his tenth studio album 

At the age of 37, he was named Emerging Artist of the Year at the Americana Music Awards in 2021. 

Charley 

Artist - Charley Crockett 4

Chris Stapleton grew up playing football in high school and studied engineering in college, before he left early and moved to Nashville to pursue music in 2001.

Stapleton wound up fronting the Nashville-based bluegrass band The SteelDrivers. Together, they released two albums, 2008’s self-titled debut and 2010’s Reckless. Shortly after the latter, he left and started a southern rock band called The Jompson Brothers, which he fronted until he was signed to Mercury Nashville in 2013 and began focusing on a solo career.

Stapleton released his debut album Traveller in 2015. It showcased his powerful vocals and equally powerful songwriting. He soon followed it with two back-to-back releases in 2017, From A Room: Volume 1 and From a Room: Volume 2.

Stapleton’s solo work has garnered Grammys, ACM Awards, CMA Awards, Billboard Music Awards and much more. Traveller swept the majors, taking home Best Country Album at the Grammys, Album of the Year at the CMAs, and Album of the Year at the ACMs.

In 2020, he released his fourth studio album Starting Over.

Chris

Artist - Chris Stapleton 1 

Courtney Marie

Album - Courtney Marie Andrews - Old Flowers

Dan Smyers didn’t cross paths with Shay Mooney until 2012 – well into their respective solo careers. But something between the two singers sparked when they met in Nashville, and soon they found themselves writing songs together. 

Despite coming from different backgrounds – Smyers from an emo band and Mooney from T-Pain's record label Nappy Boy – their first country single ‘19 You + Me’ arrived in 2014. The emotionally charged, country pop number showed off their powerful vocal duets.

Dan + Shay’s debut album Where It All Begin followed later in 2014, as did a nod from the Academy of Country Music, which nominated the duo for Vocal Duo of the Year. 

Two years later, Dan + Shay’s sophomore album Obsessed arrived, and they followed it with their third, self-titled album in 2018. 

The duo won back-to-back Grammys for Best Country Duo Group Performance, for their 2019 single ‘Tequila’ and 2020 single ‘Speechless’. Those were also banner years at the ACM Awards, where Dan + Shay took home the Duo of the Year award two years in a row. 

Dan + Shay

Country artist Darius Rucker's music career started off with a very different sound. As the lead singer for the popular '90s rock band Hootie and Blowfish, he released five best-selling albums. 

Post-Hootie, Rucker released an R&B album, 2002's

, before signing to Capitol Nashville six years later and releasing his debut country album 

The first single from the album, "Don't Think I Don't Think About It" went to number one on the Hot Country Songs chart, making Rucker the first black artist to achieve that accolade since Charley Pride in 1983. He also became the first black artist to win the New Artist Award at the CMAs.

Rucker released his second, third and fourth country albums in quick succession: 2010's 

. In between those, he released the Christmas album 

won the Grammy for Best Country Solo Performance.   

In 2012, Rucker was inducted into the Grand Ole Opry. 

came out in 2017. In 2018, Rucker was honored with the Gary Haber Lifting Lives Award at the ACM Awards.  

Darius

Artist - Darius Rucker

Singer/songwriter and folk rock pioneer David Crosby is not only a successful solo artist, but a founding member of the famed folk groups the Byrds; Crosby, Stills & Nash (CSN); and Crosby, Still, Nash & Young. 

As a result of his music with the former two musical groups, he’s been inducted into the Rock and Roll Hall of Fame twice. 

Crosby released four albums with the Byrds, beginning with the classic Mr. Tambourine Man in 1965, before he stepped away from the band in 1967. 

A chance meeting with songwriter Stephen Stills in 1968 led to the formation of a new project. When Graham Nash joined them, they began performing as folk supergroup Crosby, Stills & Nash. They released their self-titled debut album in 1969, and were named Best New Artist at the 12th Annual Grammys.

Canadian rocker Neil Young later joined CSN and they released Déjà Vu in 1969. But tensions in the band ran high and eventually the four began performing as separate duos, Crosby & Nash and Stills & Young in the mid-1970s. Crosby & Nash released four studio albums together.

CSN reunited as a trio for their second studio album, CSN, in 1977. Their third album Daylight Again followed in 1982.

In between his group projects, Crosby released his debut solo album, If Only I Could Remember My Name, in 1971. It would take another 18 years before he released his second studio album Oh Yes I Can in 1989. 

In recent years, he’s had a steady output of original solo music, including 2014’s Croz, 2016’s Lighthouse, 2017’s Skytrails and 2018’s Here If You Listen. In 2021, Crosby released his eighth studio album For Free.

Crosby was inducted into the Songwriters Hall of Fame in 2009.

David

Artist - David Crosby 1

Dierks Bentley heard Nashville calling from a young age. After visiting the city as a college student in the mid-90s, he transferred from the University of Vermont to Vanderbilt, but it would take several more years before his dream of playing music professionally became a reality.

The Best Sad Country Songs

A selection of country music's finest tearjerkers

Playlist

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The Best Willie Nelson Songs

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