The Highwaymen

Awards & Honours

Awards Won

Rankings

Covers

Records

The Highwaymen's achievements are measured not by the volume of awards but by the singularity of their collaboration. Their debut single "Highwayman" earned a Grammy, two CMA awards, and an ACM award, making it one of the most decorated country songs of the mid-1980s. The group's first two albums both achieved gold certification, a testament to their commercial appeal. All four members were individually inducted into the Country Music Hall of Fame, a distinction no other supergroup can claim. Their song "Highwayman" was ranked number one on CMT's 40 Greatest Songs of the Outlaw Country list in 2006, solidifying its place in the canon.

AwardsThe Highwaymen won eight major awards during their active period, including a Grammy for Best Country Performance by a Duo or Group with Vocal for "Highwayman" in 1986. They were named Vocal Group of the Year by both the Country Music Association (1985, 1986) and the Academy of Country Music (1986), and won Single of the Year at both ceremonies for "Highwayman." The group also received the American Music Award for Favorite Country Band, Duo or Group in 1986, and multiple TNN/Music City News Country Awards for Vocal Group of the Year.

Rankings & Lists

40 Greatest Songs of the Outlaw Country

CMT·2006

Magazine Covers

Country Music Magazine

May 1985

The Highwaymen: Outlaws Ride Again

People

June 1985

The Highwaymen: Country's Supergroup

Records & Feats

Only country supergroup with all members individually inducted into the Country Music Hall of Fame

Historic First·2004

Johnny Cash (1980), Willie Nelson (1993), Waylon Jennings (2001), and Kris Kristofferson (2004) were all inducted into the Country Music Hall of Fame, making the Highwaymen the only group whose entire membership has received that honor.

Most-streamed country supergroup song on Spotify

Streaming·2025

The Highwaymen's 'Highwayman' has accumulated over 200 million streams on Spotify, making it the most-streamed song by a country supergroup on the platform.