After its first release by songwriter Jimmy Webb in 1977, 'Highwayman' was re-recorded in 1985 by the supergroup of the same name, compromised of Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson. The tune ultimately reached No. 1 and landed on the year-end chart at No. 5 based on airplay and sales.

Although each of the four members found continued success in their iconic solo careers post-Highwaymen fame, the collective group was never able to match the success of our choice for No. 81 on the Top 100 Country Songs list.

Skip to: No. 80 | No. 60 | No. 40 | No. 20

 

 

Listen to 'Highwayman' by the Highwaymen