If you pay attention to the Optical Files annals, you'll certainly notice a pattern in the type of singer-songwriters I grew up on: sentimental but not too cheesy; rootsy but not too country; humbly poetic, slightly sardonic, with unconventional singing voices; exclusively white & exclusively male. One trope that appears over & over is the "wounded man." All of the above-linked songwriters use this archetype (though Kristofferson's friend Prine largely sidesteps it), but it's particularly ubiquitous in Kris's work. Whether he's speaking in 1st person ("Sunday Mornin' Comin' Down," "The Best of All Possible Worlds") or 3rd person ("Billy Dee," "The Pilgrim: Chapter 33"), his songs are heavily populated by down & out drunks with hearts of gold, damaged souls who talk a slick game but keep getting in their own way, & who just need the patient love of a good woman to make them whole again. "The Pilgrim" is probably the apotheosis of Kris's work in this mode: "He's a poet, he's a picker, he's a prophet, he's a pusher, he's a pilgrim & a preacher & a problem when he's stoned." Unfortunately, the prominence of the "lovable fuckup" in popular culture has given a lot of guys permission to fuck up with the assurance that they'll still be lovable. Kris's hero might be "running from his devils & reaching for the stars," but in real life a lot of these dudes forgot about the reaching for the stars part, & decided to skip the running & just embrace their devils instead, & if you get exasperated with them it's because you lack the compassion to see them as picaresque cowboys in a country song. It's one of the many ways our culture (for a long time now) reinforces the "boys will be boys" narrative, not only excusing but actually rewarding shitty male behavior. Perhaps the most barefaced example is "The Silver Tongued Devil and I," where Kris claims a split personality: the nice guy who just wants to get to know a lady, & the smooth-talking "devil" who'll say whatever he needs to get her in bed. Guess which side wins this battle of wills every time, allowing Kris to hold himself blameless because it's not actually him doing it?
While they are superficially less screwed up than the men, the women Kris writes about don't get the benefit of the same depth. The men are flawed but at least dynamic, complete humans. The women in these songs (when they appear at all) are one-dimensional, idealized angels & saints: either tragic memories ("Jody and the Kid," "Me and Bobby McGee"), innocent victims of manipulation and heartbreak ("The Silver Tongued Devil and I"), or long-suffering nurturers who are always there to pick up the pieces ("Help Me Make It Through the Night"). Whatever the particular flavor, women in these songs are always objects of love and/or lust, always exist to move the wounded man further along in his journey. No, it's not Kristofferson's fault. He didn't invent these tropes (once you tune into them you realize they are FUCKING EVERYWHERE in our mass media), but he is pretty consistent in his employment of them, & given his intelligence & leftist political perspective, you kind of hope he would break or at least challenge these patterns.
Speaking of challenging patterns: while leftist Americana fans tend to think that Republicans invaded & colonized our Workers of the World music tradition, the reality is that country music holds a pretty obvious appeal for conservatives, & even fascists, with its romanticizing of the past. Is there even such a thing as futurist country music? (Maybe Johnny Cash's verse on "Highwayman," but we'll get to that.) Kris's oeuvre is full of songs that idealize bygone times, whether it be gutter drunks longing for the simple days of childhood ("Sunday Mornin' Comin' Down," "Just the Other Side of Nowhere"), or parting couples wanting to return to when their relationship was strong ("For the Good Times," "Once More With Feeling"). Kris does challenge this trope a few times, the most interesting being "Casey's Last Ride." In a similar way to Guy Clark's "The Last Gunfighter Ballad," the song uses form to interrogate both modernity & the genre's obsession with mythologizing the past. Both the title & the musical arrangement lead us to believe we're getting an old-fashioned cowboy ballad, when in fact we are treated to a vaguely-worded story about a modern man with a lonely, unfulfilled life--the sad fallout of all that romanticized ramblin' & gamblin'.
If you've noticed that most of the songs I'm referencing are from Kris's first 2 albums, that's because this compilation, while purporting to be a career retrospective covering everything up to the late 1990s, focuses heavily on 1970 & 1971. Those first 2 albums are reproduced almost in their entirety, while later albums only get represented by a track or 2, & some albums, like 1990's brashly leftist Third World Warrior, are skipped entirely. I've made my thoughts on best-ofs known in this series, but I will say that when it comes to country music, compilations make a little more sense. The genre tends to be more song-driven than album-driven, singles have historically been more important than LPs, & artists tend to play a lot of covers & even self-covers. Still, this collection, being so disproportionately focused on a narrow slice of time, can't really claim to be a career summation. You could just listen to the Kristofferson & The Silver Tongued Devil and I albums back to back, get all the same songs as Disc 1 of this compilation, & it would only take 10 minutes longer. Okay, let's say for the sake of argument that those first 2 albums contain the bulk of Kris's best songs, & there are only a few gems scattered here & there among subsequent records. In that case, why include "Highwayman," which Kris didn't even write? Just because it was a hit? The production, lyrical perspective & group dynamic makes it vastly different from the other, rootsier, solo songs on this compilation. Even if you like that song (I do), it sticks out like a sore thumb.
It may sound like I'm coming down a little hard on old Kris here, but in reality he has a whole raft of classics under his belt. The songs can be deceptively musical, too: witness the jazzy vibraphone chords & offbeat, Willie Nelson-style phrasing of "Just the Other Side of Nowhere" & the big bold key change in the middle of "Me and Bobby McGee." Kris's reputation as a songwriter is unchallenged, but I think he's underrated as a performer. While there are dozens of high-profile covers of his songs by other artists, I tend to think that Kris's recordings of his own songs are almost always better. (The major exception, of course, is Janis Joplin's "Me and Bobby McGee.") Kris's gentle, inexorably building arrangement of "Sunday Mornin' Comin' Down" is more moving than Johnny Cash's strident version built atop that old Cash 2-step. The raw sadness & resignation of "For the Good Times" are grittier in Kris's hands than in the swooning, polished Ray Price chart-topper.
I used to love strumming & singing my simplified version of "Just the Other Side of Nowhere" when I was living overseas, an hour's drive down a dirt road on what many people would consider quite literally the other side of nowhere, thinking about home. Once I returned to the land of fast-food billboards & supermarket bread aisles the size of an entire developing-world grocery store, I still played the song, but now the other side of nowhere meant something different. Back then I fancied myself one of Kris's lovable fuckups, the ones who keep rolling those dice for a chance to clean up their act. Later on, Kris found sobriety & sharpened his political consciousness, started writing songs about inequality & speaking truth to power. It seems Kris & I grew up in the same way, so it's no surprise I feel some kinship with him. His early work gives us beautifully written but unexamined assumptions about artistic masculinity, & his later work shows us a more nuanced way forward. I just wish this compilation--like country music as a whole--weren't so stuck in the past.
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