Warren Zevon spent the late 1990s in a very strange purgatory. Like many of his singer-songwriter peers, he’d been enduring low sales and diminishing interest as his old fans aged and his new fans remained largely nonexistent. In 1995 he released what he considered to be his best album, Mutineer, and followed it up the next year with a career retrospective called I’ll Sleep When I’m Dead, both of which argued persuasively for his status as a singularly literary songwriter who hid a tender heart behind a sardonic front. And who else was writing about decapitated mercenaries and tireless diplomats in songs set in what Joan Didion once called “the far frontiers of the Monroe Doctrine”?

Those two releases reveal an idiosyncratic artist who loved a wicked turn of phrase and wrote about military juntas and broken hearts with the same gravity, but during the second half of the Clinton Administration, no one seemed to care. Zevon was unceremoniously dropped by his label, Giant Records, and for the first time in his career, he had to tour constantly just to stay afloat. The venues were growing smaller and smaller, the crowds older and older, Zevon more and more bitter. He grumbled constantly about his lot, finding himself at 50 in worse shape professionally than he’d been at 25.

And yet, he was arguably more visible than ever, thanks to a series of television appearances. Despite his disappointment on the road, he managed to turn his career troubles into sardonic comedy playing an exaggeratedly aggrieved version of himself on The Larry Sanders Show, Dream On, and Suddenly Susan. And in 1999 he did a two-week stint as David Letterman’s bandleader while Paul Schaeffer was away shooting Blues Brothers 2000 (so something good did come of that movie). That allowed him to put some of his classic songs like “Werewolves Of London” and “Lawyers, Guns & Money” in front of a whole new audience, with ample praise from Letterman himself each night.

And he was still writing songs during that time. Good ones, too. Songs about aging, songs that expressed the humiliation of pop-cultural obsolescence, songs that tackled the dire pitfalls of celebrity (others’, not his own), songs that managed to find some humor in his low state. Zevon signed a new record deal with Artemis Records — the new independent label co-founded by Danny Goldberg — and 20 years ago this Sunday he released his comeback record Life’ll Kill Ya, co-produced with Paul Q. Kolderie and Sean Slade (the team behind Hole’s Live Through This and Radiohead’s Pablo Honey). It launched something like a renaissance for Zevon, albeit one cut tragically short. Two years later he was diagnosed with pleural mesothelioma. He died in 2003.

His highly public battle with cancer — Letterman devoted an entire show to Zevon in 2002 — has since cast Life’ll Kill Ya in a grimmer light. Despite that title, it is not an album about facing down death. He was only just starting to feel his age. These are songs about getting to a point in life where you just start thinking about facing down death. “I may be old and I may be bent, but I had the money till it all got spent,” he sings on opener “I Was In The House When The House Burned Down.” It’s an offhand remark in a song about surviving great tribulations in the music industry, but now it carries a different kind of weight than he might have intended.

But he is taking stock of what was lost during those trials, and since this is Zevon we’re talking about — the guy who got the Eagles to harmonize on a song making fun of the Eagles — he approaches what he must have assumed was middle age with shit-eating grin intact. On one of the album’s standouts, pointedly titled “My Shit’s Fucked Up,” he considers mortality in the most vulgar language imaginable, recounting (or perhaps predicting) a doctor’s dire prognosis: “He said, ‘I’ll break it to you, son. Your shit’s fucked up.'” With each verse Zevon strips away the humor and rearranges those expletives until he’s left with an essential, animating sadness: “That amazing grace sort of passed you by/ You wake up every morning and you start to cry.” That’s some fucked-up shit.

Life’ll Kill Ya ends with “Don’t Let Us Get Sick,” which in retrospect sounds like Zevon tempting fate. But there’s something very generous in that title, specifically in that first-person-plural pronoun: This isn’t a prayer for his own body, but for those of his friends, his fans, everyone. “I thought of my friends and the troubles they’ve had,” Zevon sings, “to keep me from thinking of mine.” He finds some hard-won solace in that community of loved ones: “I’m lucky to be here with someone I like, who maketh my spirit to shine.” Especially after spending so many years on the road, that last line sounds like he wrote it explicitly for the stage: a sentiment intended for his audience, however many they number.

It’s easy to focus on songs like those, which seem to provide clues to an upcoming plot twist. What gets lost is how much fun Zevon seems to be having, both with his words and his music. “Porcelain Monkey” is his second jab at Elvis Presley, who is depicted as miserable in his success and its tacky spoils. “Hip-shakin’ shoutin’ in gold lamé, that’s how he earned his regal sobriquet,” he sings of the King of Rock & Roll, delivering that last word with a wink: Zevon knows he’s the only songwriter who could make “sobriquet” sound so good in a rock song.

As a teenager Zevon had been a student of Igor Stravinsky, and for decades he nursed ambitions to compose classical music. He only got as far as scoring a few films and television shows, but he managed to add some intriguing flourishes to his final albums, including Life’ll Kill Ya. Diagonal piano chords intersect the straight melodic lines of the title track, keeping the song off balance; it’s the musical equivalent of leaning too far back in your chair. Zevon also shows off his gift for rock and roll mimicry: “For My Next Trick I’ll Need A Volunteer” could be a lost Randy Newman song, and it’s followed by “I’ll Slow You Down,” which gets to the Byrds by way of Tom Petty. At times the man himself is obscured by such references, the parodist overshadowed by his targets, but Zevon is always present in these songs, even if he’s just lurking in the wings.

As an Artemis artist, Zevon would make two more albums before his death: My Ride’s Here in 2002 and The Wind in 2003. Together with Life’ll Kill Ya, they comprise a trilogy of sorts, and what’s remarkable about them is how front-and-center Zevon makes himself. A lifelong parodist whose albums are weighted down with famous cameos, he strips everything back and allows himself and his fears to become his truest subject. He becomes the object of his own wicked fascination. By turning inward, he managed to go out on top.