Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson first performed as the Highwaymen in 1985, after which they became a going concern for the next decade. Hits didn't often arrive -- their 1985 debut reached the top of Billboard's Country Album charts and its title track achieved the same feat on the singles chart -- but they became a reliable concert attraction after the release of Highwayman 2 in 1990. The 2016 archival release of Live: American Outlaws is the first official document of this part of the supergroup's life, providing the first-ever CD release of the March 14, 1990 show recorded at Nassau Coliseum that was previously released on VHS in 1991 (the video portion has been remastered and released as a DVD in this set), along with a third CD featuring a six-song set from 1992's Farm Aid V, four songs from 1993's Farm Aid VI, and a spruced-up outtake of Bob Dylan's "One Too Many Mornings," where Nelson and Kristofferson added new vocal harmonies to a recording from Cash and Jennings' 1986 LP Heroes.
Although all three of the concerts here were events by some measure, the Farm Aid gigs were high-profile charity shows, while the Nassau gig was intended for home video release. Considering this, it's odd how none of the three live dates feel like major events. All are matter-of-fact performances, the four Highwaymen relying on some measure of seasoned chops and personal charm as they trade songs, or perhaps just lines, on a collection of greatest-hits and new tunes they're plugging. The latter served as an excuse to get the band out on the road and they fade into the woodwork here, overshadowed by a collection of tunes that amount to some of the greatest songs of the 20th century. None of the renditions here are anywhere close to definitive -- the Highwaymen wear their age on their sleeves a bit, plus the productions are slick and overblown in a manner standard to big-budget shows of the '80s and '90s -- but something that would've seemed as little more than an enjoyable night out in 1990 now seems like something modestly special. Hearing these four Titans interact on-stage, harmonizing and cracking wise, it's hard not to marvel at the fact that for a while, Jennings, Nelson, Cash, and Kristofferson actually roamed from town to town, singing their songs along the way. This is a simple document of that time that seems more momentous now that the era has passed.