One of my fondest memories of growing up is riding along with my dad in his green Ford pick-up truck, listening to Johnny Cash's Live at Folsom Prison on eight-track tape. (Yes, eight-track. I'm no spring chicken, my friend.) It's a little foggy, the memory, as I was still in the single digits back then, so maybe I'm wrong about the pick-up truck. Maybe that came later, and I was actually listening to Johnny while cruising along in a blue Maverick, or possibly an orange Datsun. But that caveat having been offered, it doesn't change the fact that, to this day, I can still sing "Dirty Old Egg Sucking Dog" and "Flushed from the Bathroom of Your Heart" word for word. I have equally warm recollections of listening to a cassette tape of Willie Nelson and Waylon Jennings crooning "Luckenbach, Texas (Back to the Basics of Love)" and "Mamas Don't Let Your Babies Grow Up to Be Cowboys".
So when I heard about the debut album by the Highwaymen being released in 1985, I thought, "Sweet! Johnny Cash, Waylon Jennings, and Willie Nelson all singing and playing together!" And, yet, when I actually looked at the country equivalent of Mount Rushmore staring out from the cover of the album, all I could think was, "Who's the guy on the far right and what the hell does he think he's doing up there with Johnny, Waylon, and Willie?" "The guy on the far right," of course, was Kris Kristofferson. And, with a bit more reflection, I'm sure I recognized him, but not from his music. Not really, anyway. No, if anything, I probably thought, "Hey, that guy was on The Muppet Show!" (Season Three, baby. He co-hosted with his then-wife Rita Coolidge. Check it out.)
Somehow, my education in country music had managed to omit poor Kris. What I would later come to realize, however, was that I had actually come to know some of his work without actually knowing it was his. I'd certainly heard Janis Joplin's version of "Me and Bobby McGee", probably Johnny Cash's interpretation of "Sunday Morning Coming Down", and, given how many times it's been covered, I can't imagine I hadn't at least heard someone's version of "Help Me Make It through the Night" (probably Glen Campbell's). Still, Kris Kristofferson is definitely the least-familiar member of the Highwaymen to mainstream America when it comes to his music (his face, of course, is easy identifiable from his film and television work).
Thanks to Legacy Recordings, there's now a stellar introduction to the man's material: the two-disc Essential Kris Kristofferson. It isn't the first best-of he's had released, and it might not even be the best, but it's no less a fine sampling of Kristofferson's career to date, or, at least, of his work on Monument and Columbia, anyway. Essential is more than a little top-heavy with material from Kristofferson's early years. Disc 1 contains ten songs from his 1970 debut (11 if you count "Come Sundown", a demo of which is tacked onto the 2001 CD re-release of Kristofferson), seven from 1971's The Silver-Tongued Devil and I, and a solo version of "From the Bottle to the Bottom", which he later recorded with Coolidge for '73's Full Moon. Disc two, meanwhile, is far more sprawling, essentially covering from 1972 to 1985.
Spending 18 tracks on two years' worth of material, then 19 tracks on 13 years' worth certainly makes the majority of Kristofferson's work post-1971 seem decidedly less than essential. While Disc 1 might well contain the work that made Kristofferson a legend in the country music community, Disc two certainly isn't without merit. For one, the Jimmy Webb-composed "theme song" for the Highwaymen is about as perfect a meeting of four country legends as you could hope for even if only Johnny Cash could get away with singing the line, "I fly a starship 'cross the universe divide." The John Prine-dedicated "Jesus Was A Capricorn" is certainly a classic, and you can't fault any duet with Willie Nelson ("How You Do Feel about Foolin' Around"). But the second disc is decidedly uneven and isn't nearly as representative of Kristofferson's later work as the first disc is of his earliest material. It might not be as memorable as the stuff from the early '70s, but it still doesn't deserve quite as short a shrift as this.
Missing in action altogether are such tracks as "You Show Me Yours and I'll Show You Mine", "I Got a Life of My Own", and "Who's to Bless and Who's to Blame", but perhaps that's done to give other Kristofferson best-of collections a reason to remain in print. It's arguable that The Essential Kris Kristofferson is inferior to 1991's two-disc compilation Singer/Songwriter, which takes the interesting tactic of offering a disc of Kristofferson's original versions alongside the often-more-successful cover versions by other artists, thereby offering a fuller picture of what he's accomplished as both a songwriter and a recording artist. Additionally, by not touching much of anything beyond 1985, this certainly isn't a definitive collection by any means.
Nonetheless, the material contained within these two discs is more than enough to clarify exactly how Kris Kristofferson earned his position within the Highwaymen.
Post-Script: In a moment of pure serendipity (thereby giving me the opportunity to use the word "serendipity" in a sentence for the first time in my career in journalism), less than three hours after writing this review, I attended the Williamsburg Film Festival and was introduced to Alan Rush, who worked at Monument with Kris Kristofferson and, among his many other studio and songwriting credits, played on Jesus Was a Capricorn. When I told him about the review I'd written that morning, he asked with amusement if his name made it into the credits of The Essential Kris Kristofferson. (It does.) He then admitted that the aforementioned Singer/Songwriter collection might actually be the better way to investigate Kristofferson's work. "He's a brilliant songwriter," Rush easily acknowledged, "but he isn't necessarily the best interpreter of his own songs." He then went on to offer up several anecdotes about Kristofferson's contemporaries that I'd love to regale you with, if it wasn't for the fact that virtually all of them are probably libelous. Damn.