5 Songs That Made The Highwaymen A Rock n’ Roll Success

The rakish glee of the country supergroup named Highwaymen seems too good to be true. The four titans of outlaw country music joined forces to create songs that are easily a country classic for the people to appreciate the genre better. For that reason alone, as well as the phenomenal tracks that they have produced in the span of their careers inside the group, the country genre will forever live inside our radio stations. We present to you the five songs that made the Highwaymen a success in the classic rock era.

“Highwayman” – Highwayman (1985)

“Highwayman” isn’t an original one from Highwaymen, but they were the ones who threw the song to its commercial success. The resulting favor also pulled their album of the same name to triumph, spending almost 20 weeks on top of the country charts. It’s their debut single and is arguably their best song.

“Desperados Waiting for a Train” – Highwayman (1985)

The second single is also a cover song from the group, originally recorded by Jerry Jeff Walker back in 1975. Though unlike the “Highwayman”, it didn’t chart in the top 10, yet it’s a fan favorite.

“Silver Stallion” – Highwayman 2 (1990)

The 2nd album of Highwaymen was a pressure for the group to regain its status much like its predecessor. By this time as well, the artists have released their songs individually but were not met with critical reception. Highwayman 2 was a product of their will to regain their status back. They have covered some songs including this Lee Clayton-penned song “Silver Stallion”.

“Born and Raised in Black and White” – Highwayman 2 (1990)

Highwaymen 2 did not top the country charts, but it did however placed at the 4th spot comfortably. As mentioned earlier, the rockers are desperate to regain their positions back, and they did so with their 2nd single “Born and Raised in Black and White”. It didn’t gain a spot on the billboards, but it peaked no. 1 at the Hot Country Radio Breakouts, so everything is worth it still.

“Against The Wind” – Highwayman (1985)

Another cover song that the Highwaymen fellas include to their magnificent first album. The song was a Bob Seger classic and helped the latter earned his fame onwards.