On this day back in 1986, Willie Nelson, Waylon Jennings, Johnny Cash, and Kris Kristofferson were presented a Gold Album for The Highwaymen. Though they would end up being called The Highwaymen, the group did not have an official name when they released the album on Columbia Records.
The single “Highwayman” became a #1 country hit.
On this day in 1987, Waylon Jennings’ “Rose In Paradise” entered the Country Charts. The song was released as the first single from the album Hangin’ Tough.
“Rose in Paradise” was Waylon Jennings’ twelfth number one country single. It would be Waylon’s Last #1 record.
On this day in 1978, Waylon Jennings’ album I’ve Always Been Crazy was Certified Gold. The album featured a medley of Buddy Holly hits, including “Well All Right” “It’s So Easy” “Maybe Baby” & “Peggy sue”, as well as a cover of Johnny Cash’s “I Walk the Line.
The album was Jennings’ way to sum up his negative feelings towards the music industry, and how he felt about people who criticized his “Outlaw” lifestyle.
On this day in 2001, the CMA announced that Waylon Jennings, Webb Pierce and the Everly Brothers would be among the “Class of 2001” to be inducted into the Country Music Hall of Fame.
On this day in 2007, the Academy of Country Music presented the Cliffie Stone Pioneer Award to Dolly Parton, Waylon Jennings, Don Williams and songwriter Harlan Howard.
On this day back in 1986, the made-for-tv movie Stagecoach starring Willie Nelson, Johnny Cash, Kris Kristofferson, Waylon Jennings and John Schneider first aired. The movie is a remake of the 1939 classic of the same name. Kris Kristofferson plays the Ringo Kid, originally played by the legendary John Wayne. Willie Nelson portrays the infamous Doc Holliday, while Johnny Cash plays Marshal Curly Wilcox and Waylon Jennings plays Hatfield, the gambler.
On this day in 1985, Johnny Cash, Willie Nelson, Waylon Jennings and Kris Kristofferson’s album The Highway Man was released. The album was released after their collective single “Highway Man” went number one. “Highway Man” was followed up by the Top 20 hit “Desperados Waiting for a Train.” The album would top the U.S. Billboard Top Country Albums chart.
The foursome would go on to be called The Highway Men.
On this day in 1985, Wanted: The Outlaws, featuring Waylon Jennings, Willie Nelson, Jessi Colter and Tompall Glaser, was certified double-platinum, along with the album Waylon & Willie.
On this day in 1985, Waylon Jennings, Johnny Cash, Willie Nelson and Kris Kristofferson – collectively known as The Highwaymen- topped the chart with their song “Highway Man.” The song spent a total 20 weeks on the chart and finished 1985 as the 5th country song in terms of airplay. “Highway Man” also earned songwriter Jimmy Webb a Grammy Award for “Best Country Song.”
On this day in 1976, Waylon Jennings captured the top spot on the chart with “Amanda.” “Amanda” was Jenning’s eighth solo number one on the country charts. The song was first recorded and released by country singer Don Williams in 1973. Williams rendition of “Amanda” peaked at number 33 on the Billboard Hot Country Singles Chart.