Celebrate the Heart of Country, Americana, and Roots Music!

Drop Us A Line, Y'all

Y'all interested in advertising, partnering up, contributing stories, joining our team, or just got a question? Well, don't be shy, drop us a line!

Follow Us

Country Music’s Classic Supergroup, The Highwaymen Sings ‘Highwayman’

Country Music's original supergroup, The Highwaymen, sing their song "Highwaymen"
by
  • Riley is a Senior Country Music Journalist for Country Thang Daily, known for her engaging storytelling and insightful coverage of the genre.
  • Before joining Country Thang Daily, Riley developed her expertise at Billboard and People magazine, focusing on feature stories and music reviews.
  • Riley has a Bachelor of Arts in Journalism from Belmont University, with a minor in Cultural Studies.

Country music won’t be the same without the supergroup that made the greatest hits of all time. When the Highwaymen decided to make music together in 1985, they made history. Their combined talents pulled fans across the globe, making their songs some of the most enduring classic hits.

The Highwaymen had an interesting start. Their official name wasn’t coined yet even after the release of their first two albums. However, Jimmy Webb’s hit from 1977 gave them a hint. 

Later on, the four indisputable talents found their name that would later create a timeless mark in the country music industry. Their first album was the Number 1 platinum-selling album. Meanwhile, their song called “Highwayman” remained on the top spot on the Billboard Hot Country Songs chart for around five months.

RELATED: Before Boy Bands Were Cool, There Were The Highwaymen

Given their skills in music, fans always loved whenever they got together. Willie Nelson, Waylon Jennings, Johnny Cash, and Kris Kristofferson make it easy for fans to go wild. That’s what happened when they appeared at the 1993 Farm Aid concert. For their fans and country music lovers, this performance is worth a thousand replays.

Before they bewildered the spectators with their performance, Johnny Cash went upstage to say a few things to his friends and fellow group members. 

He thanked the rest of them and remembered their fantastic time together. Cash reminded fans about how they conquered the world together, playing wonderful country music. After he called the rest of the members, the Highwaymen started rocking the stage.

RELATED: The Highwaymen’s Performance Of “Me And Bobby McGee” Proves Why They’re The Best In Country Music

During the performance, they proved how they made more than music, but also a lasting friendship.

As the Highwaymen sang “Highwayman,” their unique vocals and amazing talent made all the fans love country music all the more.

See their performance for yourself. Watch The Highwaymen sing “Highwayman” below:

Latest Stories

Tina Knowles, Beyonce's mom watched the Grammys with Beyoncé’s kids, reacting with surprise as Beyoncé won Best Country Album.

Beyoncé’s Mom Was Shocked by Her Country Grammy Win: “I Couldn’t Believe It”

The 2025 Grammy Awards had their share of eyebrow-raising moments. Still, nothing felt more out of place than Beyoncé walking away with Best Country Album for “Cowboy Carter.” While her ...

Willie Nelson defied country music norms with outlaw spirit, genre-bending collaborations, and a fearless approach to his craft.

5 Times Willie Nelson Proved He Wasn’t Bound by the Rules of Country Music

Willie Nelson isn’t just a country music legend—he’s a rebel, a rule-breaker, and a pioneer who never let Nashville’s expectations define him. From his unconventional albums to genre-bending collaborations, Nelson ...

Martina McBride did not call Beyoncé a 'clown in a cowboy hat'; the viral claim is false and has no evidence to support it.

Martina McBride Never Called Beyoncé a “Clown in a Cowboy Hat”

Social media has a way of turning fiction into fact overnight, and the latest victim of misinformation is country legend Martina McBride. A viral claim has been circulating that McBride ...

Chris Stapleton did not object to Beyoncé’s country Grammy win, dismissing rumors of controversy over her Cowboy Carter victory.

No, Chris Stapleton Did Not Object to Beyoncé’s Grammy Win

Rumor has spread that Chris Stapleton filed an “official objection” after Beyoncé won Best Country Album at the 2025 Grammys for Cowboy Carter. A supposed quote attributed to him suggests ...

Blake Shelton to host the Grand Ole Opry's 100th celebration, honoring a century of country music with star-studded performances.

Blake Shelton Set to Host Grand Ole Opry’s 100th Celebration

Country music’s most legendary stage is set for a once-in-a-lifetime celebration. Blake Shelton is taking the reins. The Grand Ole Opry will mark its 100th anniversary with a star-studded NBC ...

Dolly Parton fights to save her Imagination Library in Indiana after budget cuts threaten its vital funding for children's literacy.

Dolly Parton Fights to Save Imagination Library in Indiana

Dolly Parton has always stood up for what she believes in—lifting people’s spirits with her music, funding major charitable efforts, and ensuring children have access to books, no matter their ...

Billy Currington maintains a private personal life, sparking speculation about his sexuality, though no public statement or evidence confirms the rumors.

Is Billy Currington Gay? What We Know About the Country Star

Billy Currington has spent decades serenading country music fans with hits like “People Are Cr𝐚zy” and “Must Be Doin’ Somethin’ Right.” His smooth vocals, laid-back charm, and undeniable talent have ...

Post Malone and Alan Jackson pose together, bridging generations of country music with their iconic styles and shared respect for the genre.

Post Malone’s Road to Country Music Started Long Ago

Post Malone didn’t just wake up one morning and decide to go country—he’s been headed down this dirt road for a long time. From his Texas roots to his early ...

Drake sparks speculation about a country music crossover, potentially releasing a country album and exploring a new genre.

Is Drake the Next Artist to Take Over Country Music?

Country music has been through a wave of change lately, and not everyone is convinced it’s for the better. Beyoncé’s Cowboy Carter shook the industry, bringing country into the mainstream ...

Riley Green's 'Worst Way' music video sparks a frenzy with steamy scenes and a touch of humor, making waves in the country music world.

Riley Green Turns Up the Heat in Worst Way Music Video

Riley Green isn’t holding back in his latest music video for “Worst Way,” and fans are feeling some kind of way about it. Known for his rugged country charm and ...