Graphic - The Best Country Songs About Flying

A playlist of the best country songs about flying

The Best Country Songs About Flying

“If you cannot teach me to fly, teach me to sing,” Peter Pan says in the enduring J.M Barrie classic, and ever since Wilbur and Oliver Wright invented and flew the first airplane, singers and songwriters have been taking that to heart and looking up to the skies for inspiration.

Country singers are no exception. Everyone from John Denver to Drive-By Truckers has got a song about flying of some description, and when it comes to airports and airplanes everyone has a different approach.

While Dierks Bentley is jetting off to Cancun and getting drunk on his Boeing 737, Cassadee Pope is still back at the airport lurking about and mooning over everyone kissing each other.

Of course, there has been tragedy too, and country music has lost some of its greatest voices to plane crashes over the years. Patsy Cline, John Denver and Jim Reeves are just a few of the country legends that have been taken from us too soon.

It’s like Miranda Lambert once sang: “If you don’t jump, you’ll never know if you can fly.” So, what are you waiting for? Take a leap into the unknown with our playlist of the Best Country Songs About Flying. Yes, ‘Free Bird’ is on it.

Listen to our Holler playlist of the Best Country Songs About Flying below:

Drunk On A Plane

Leaving On A Jet Plane

Let Him Fly

Flying or Crying

Kisses at Aiports

Time For Me To Fly

Flyin' Shoes

The Cape

Wings

Flying Visit

Fly Over States

If Love Was A Plane

Free Bird

Born To Fly

Silver Wings

If You're Gonna Fly Away

Outbound Plane

Baggage Claim

L.A. International Aiport

Flying over Water

Eagle When She Flies

Expecting To Fly

Watching Airplanes

All the Time in Airports

Boeing Boeing 707

Let Her Fly

To The Aiport

I'll Fly Away

Fly Me to the Moon

If I Could Only Fly

Up and Flying

Faster than My Angels Can Fly

God Made Airplanes

Fly Trouble

Airplane

Paper Airplane

Shut Up and Get on the Plane

To Live is to Fly

Tired of Flying

Flying Out Of London

Falling and Flying

Flying Colors

Flying Cowboys

Flying Silver Eagle

This Plane Don't Go There

If My Heart Had Wings

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50 of The Best Country Songs About Flying on Holler

Ever since Wilbur and Oliver Wright invented the airplane, country singers and songwriters have been looking up to the skies for inspiration. Listen to our Holler playlist of the Best Country Songs About Flying.

The Best Country Songs About Flying playlist | Holler

Writer on country music and fear for Holler, The Line Of Best Fit, Rough Trade Magazine and Riposte. Also a singer and songwriter with The Boy Least Likely To and Legends Of Country. Born and raised in the countryside but lives in London.

Contributor - Jof Owen

Hailing from Castlewood, Virginia, 49 Winchester have always sought to incorporate the conflicting impulses of both longing for home and longing for the road into their music. Over the course of their four studio albums, the eight-piece band’s Appalachian folk has gradually blossomed into a rockier and more rough-around-the-edges sound.

49 Winchester have patiently built a loyal following over the course of their three independently released albums, which began back in 2014 with their self-titled debut release. This was followed by 

 in 2018, before the trio was completed by 

The band’s mercurial, definition-defying style caught the attention of Nashville’s go-to label for Americana and alt-country music, New West Records.

In 2022, 49 Winchester released their first album with New West, 

. the project received far-reaching acclaim, and served as a celebration of the band’s roots in Virginia.

The playful artwork depicts a coal miner, embodying 49 Winchester’s continued determination to pay homage to the blue collar traditions that have long formed the backbone of country music, as epitomised on ‘Hillbilly Daydream’.

elevated 49 Winchester from regional heroes to national prodigies. Various outlets championed the group for their eclectic mix of influences, with Holler naming the 2022 album as one of its Albums of the Year.

In 2023, 49 Winchester are set to embark on a hotly anticipated tour across the US, which will see them playing in Tennessee, Arizona and more.

Home of all the latest news, information and coverage of 49 Winchester on Holler.

49 Winchester

Artist - 49 Winchester

49 Winchester have always sought to incorporate the conflicting impulses of both longing for home and longing for the road into their music.

49 Winchester: News, Songs & Reviews | Holler

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, 

Home of all the latest news, information and coverage of Allison Russell on Holler.

Allison

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For Allison, music became an outlet to escape her troubled home. 

Allison Russell: News, Songs & Reviews | Holler

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Amanda

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Artist - Amanda Shires 1

Amanda Shires: News, Songs & Reviews | Holler

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Amythyst Kiah: News, Songs & Reviews | Holler

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 

Home of all the latest news, information and coverage of Ashley Monroe on Holler.

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Monroe's music is emotionally driven pop-country, she continues to soar to the top of her career after facing her artistic arc.  

Ashley Monroe: News, Songs & Reviews | Holler

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.

Home of all the latest news, information and coverage of Ashley McBryde on Holler.

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McBryde' popular song 'A Little Dive Bar in Dahlonega' is about having the worst day but making the best of it. 

Ashley McBryde: News, Songs & Reviews | Holler

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. 

Following an eclectic self-titled EP in 2020, BRELAND put out the sobering and emotionally raw 

 EP, which he released in response to the Black Lives Matter protests that spread across the US that summer. 

In 2022, BRELAND released his debut album, 

, which featured collaborations with Thomas Rhett, Keith Urban, Ingrid Andress and more. The project's name captured the sonic mercuriality that has made BRELAND one of the most exciting new voices in country music. 

Home of all the latest news, information and coverage of BRELAND on Holler.

BRELAND

Artist - Breland 

BRELAND is a cross country artist with a sound that integrates elements trap, hip-hop, R&B and soul.

Breland: News, Songs & Reviews | Holler

 EP in June 2022, it became the biggest streaming country debut of all time. Zimmerman also became one of just three country artists to earn over a million streams on each track during street week alone. The other two artists? None other than Luke Combs and Zach Bryan.

It’s sometimes difficult to believe that Bailey Zimmerman is still in his early twenties, and that he’s only been releasing music since 2021. In the space of just over a year, Zimmerman has enjoyed an ascent that has felt so meteoric, that he seems to have already transcended the labels of ‘prodigy’ and ‘prospect’.

‘Fall in Love’, one of the highlights from his 2022 EP, became his first Country Radio No. 1 in December. The single serves as the perfect encapsulation of what makes Zimmerman such a threat. It has the signature rasp and heart-wrenching intensity that pervades much of the project, but - crucially - it is packaged up with a pop-leaning production style that makes it ideal for Country Radio.

The result is a sound that simultaneously straddles both the mainstream and the outer edges of the modern country landscape. Part of Zimmerman’s ability to infiltrate both markets can be traced back to his blue collar roots, having grown up working on a gas pipeline.

In 2023, Zimmerman is joining Morgan Wallen on his blockbuster 

world tour. Zimmerman has previously cited Wallen as a mentor, with the Sneedville native having even co-written ‘Trainwreck’ from the 

When he heads out on the road with Morgan Wallen, Zimmerman will receive a first-hand glimpse into what it takes to become one of the biggest country stars on the planet. Given how emphatic Zimmerman’s emergence has been so far, few would be surprised to see him unveil his own world tour this time next year.

Home of all the latest news, information and coverage of Bailey Zimmerman on Holler.

Bailey

Artist - Bailey Zimmerman 5

Zimmerman has enjoyed an ascent that has felt so meteoric, that he seems to have already transcended the labels of ‘prodigy’ and ‘prospect’.

Bailey Zimmerman: News, Songs & Reviews | Holler

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. 

Home of all the latest news, information and coverage of Blake Shelton on Holler

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Artist - Blake Shelton

Blake Shelton served as a coach on NBC's The Voice, 2017's People's Sexiest Man Alive and is a legendary country music artist with either Grammy nominations.

Blake Shelton: News, Songs & Reviews | Holler

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Bob Dylan: News, Songs & Reviews | Holler

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. 

Home of all the latest news, information and coverage of Brandi Carlile on Holler.

Brandi

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Carlile learned how to sing and play guitar and piano during her early years, translating those talents into a remarkable storytelling ability and perception.

Brandi Carlile: News, Songs & Reviews | Holler

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Brandy Clark: News, Songs & Reviews | Holler

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.

Home of all the latest news, information and coverage of Brett Eldredge on Holler.

Brett

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Eldredge is a country singer with a soulful voice that radiates from his jazzy vocal numbers growing up.

Brett Eldredge: News, Songs & Reviews | Holler

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. 

Home of all the latest news, information and coverage of Brittney Spencer on Holler.

Brittney

Artist - Brittney Spencer 3

Spencer grew up in a gospel environment early on but with a little nudge from a friend, she found her calling in country music.

Playlist

The Best Country Songs About Flying

Dierks Bentley

John Denver

The Chicks

Zach Bryan

Cassadee Pope

Dolly Parton

Maddie and Tae

Townes Van Zandt

Guy Clark

Jackson Dean

Ferris & Sylvester

Jason Aldean

Brad Paisley

Lynyrd Skynyrd

Sara Evans

Merle Haggard

Faith Hill

Nanci Griffith

Miranda Lambert

Susan Raye

Jason Isbell

Dolly Parton

Buffalo Springfield

Gary Allan

The Handsome Family

Roger Miller

Dolly Parton, Loretta Lynn and Tammy Wynette

Nickel Creek

Johnny Cash

Willie Nelson

Merle Haggard and Willie Nelson

Reba McEntire

Eric Church

Jason Aldean

Hank Williams

Suzy Boggus

Lady A

Indigo Girls

Alison Krauss and Union Station

Drive-By Truckers

Steve Earle

Ryan Kinder, Brandy Clark and Jerry Douglas

The Long Ryders

Hunter Hayes

Keith Whitley

Rickie Lee Jones

Jamey Johnson

Kezia Gill

Jason Aldean

Faith Hill

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