The Highwaymen’s trip started in 1985 and wrapped up one decade later. The result was something rarely seen during the early days of country music’s climb into the mainstream: a group of elder statesmen who could still top the charts, speeding past the younger acts of the genre. Cash was part of that lineup too, teaming up with his old roommate Waylon Jennings and Texas titans Kris Kristofferson and Willie Nelson. Nearly 30 years after Elvis Presley, Jerry Lee Lewis, Carl Perkins and Johnny Cash all swapped gospel harmonies during the “Million Dollar Quartet” jam at Sun Studio in 1956, a different sort of supergroup - the Highwaymen - released their first album.