“If it sounds country, man, that’s what it is. It’s a country song.” One of the more iconic openings to one of the 20th century’s more iconic songs, Kris Kristofferson’s eye-roll is nearly audible in the first seconds of “Me and Bobby McGee”. His songs, after all, travelled far beyond the narrow confines of Nashville. “Me and Bobby McGee” would shortly become fellow Texan Janis Joplin’s posthumous signature, and this album’s three other canonical entries—the stunning ballads “Help Me Make It Through the Night”, “For the Good Times” and “Sunday Mornin’ Comin’ Down”—were brought to the charts by artists as diverse as Gladys Knight, Perry Como and Johnny Cash. A fitting introduction, then, for perhaps the most idiosyncratic of the outlaws: having already proven himself as a Rhodes Scholar, boxer, soldier and helicopter pilot (among other occupations), Kristofferson had turned to songwriting, selling most of these songs to other artists before he finally got his own record deal. That deal came courtesy of Cash, who invited Kristofferson onstage during his set at the 1969 Newport Folk Festival; stardom as a singer and actor followed soon after. This album was not a hit, but its songs are seminal and the release endures as a pivotal entry in the songwriter-first, singer-second catalogue that forced Music Row to slowly turn its head towards the outlaws. That term “outlaw” hadn’t yet been attached to Kristofferson and his peers—hippie, mostly Texan songwriters who were resistant to the Nashville Sound—when this album was released, but his countercultural defiance is centered from this album’s first line, an indictment of “Mr Marvin Middle Class”. “The Law Is for Protection of the People” and “Best Of All Possible Worlds” chronicle wrongful arrests; “Casey’s Last Ride” and “Darby’s Castle” are as much indictments of bourgeois values as “Bobby McGee” is a haunting ode to fading ’60s idealism. Kristofferson marked the dawn of one of the 20th century’s signature talents, and the expansion of a still-new archetype: the songwriter’s songwriter, principled and uncompromising in their belief in the power of three chords and the truth.