In the years since the first Highwaymen album, a new crop of younger stars, such as Randy Travis, Steve Earle, and Dwight Yoakam had emerged, and country radio shifted its focus accordingly.

Kristofferson biographer Stephen Miller notes, "Moman produced in such a fashion – prominent drums, electric guitars, and organs – as to bring rock values to songs that, with a different approach, could just as easily have been pure country.

[2] There were rumours of clashing egos and flare-ups, in part fuelled by Kristofferson's penchant for sounding off on his political views and opposition to American foreign policy.

We saw it as one nonstop transcontinental party…I don’t mean that we didn’t get a little cranky from time to time…For the most part, though, it was smooth sailing.”[3] Highwayman 2 spent 40 weeks on the country chart, peaking at number 4.

Sadly, of the ten tracks, only six were penned by any of the members…Overall, Highwayman 2 features a decent set of rather uneventful songs, but only the most dedicated fan will find this album a necessity.”