From as early as his teenage years, it was plain that Warren Zevon was never going to be an ordinary person, or at the very least an ordinary writer. In the oral biography compiled by his first wife Crystal, I’ll Sleep When I’m Dead, it is written that upon hearing the death of John F. Kennedy being announced over the loudspeakers at his high school, Zevon turned to his friend Danny McFarland, who recalls his macabre candor:

…Warren took his right hand and stretched it behind his back; at the same time he looked over his right shoulder and said in his best JFK accent, “Jackie, I’ve got this real bad pain in my head.”

His tumultuously productive career as a songwriter only further demonstrates his unmitigated interest in the dark side of life, whether it be the Hyatt House S&M of “Poor Poor Pitiful Me” or the Uzi atop the ballerina shoes on the back of the sleeve art to his third LP, Bad Luck Streak in Dancing School. At the end of his career—both before and following being diagnosed with mesothelioma, a terminal form of lung cancer—he put out albums with titles including Life’ll Kill Ya and My Ride’s Here. It wasn’t just that Zevon was spitting in Death’s face—he pulled up a barstool next to the hooded reaper, ordered whiskeys for the both of them, and challenged him to a conversation. If Zevon’s lyrics are any indication, he greeted Death as an old friend, one who knew all of his stories long before the scythe bore down.

While Zevon’s signature darkness is indeed one of the characteristics that makes him so distinctive a songwriter, there’s a tender heart a few inches below the skull wearing aviator sunglasses. Songs like “Empty-Handed Heart” and “Hasten Down the Wind” early in his career and “Don’t Let Us Get Sick” as his time came to a close gave the public a portrait of a man who, while uniquely able to handle the harsh realities of life, hadn’t become desensitized to the pains of living — the self-deprecating “Numb as a Statue” notwithstanding. Part of what makes his morbid tracks so powerful are all the times where he’s unflinchingly honest; someone willing to face off with the bleakest aspects of humanity is bound to get a few tears sliced into his armor.

Those who counted Zevon as a close friend — Jackson Browne, Jorge Calderon, and Carl Hiaasen, amongst others — are familiar with his weaknesses, as is anyone who has read the gripping, painful tales in I’ll Sleep When I’m Dead. During his peak of popularity, following the “Werewolves of London”-backed LP Excitable Boy, he was frequently angry, reckless, and consumed by alcohol. Following 1982’s The Envoy, he publicly fell off the wagon, resulting in a five-year creative hiatus. To use the words of one of The Envoy‘s best tracks, much of his life “ain’t that pretty at all”.

But for all the wrongs Zevon etched into the world, he gave back an incredible amount of humor, wisdom, and grace. His death at 56, while perhaps fitting given his career-long banter with death, was undeniably tragic. Much like the rebels of “Frank and Jesse James”, he died too young. Ten years have passed since Warren’s demise, but his songs have yet to lose any of their acerbic vitality.

Narrowing down Zevon’s literate oeuvre into a ten-best list is a feat impossible; too much genius has to be left off. From the jilted, hilarious Hawaiian romance of “The Hula Hula Boys” to the paranoid spy thriller “You’re a Whole Different Person When You’re Scared”, from the embrace of second place in “Looking for the Next Best Thing” to the touching plea for forgiveness in “Reconsider Me” — Warren left his fans, friends, and family with a bevy of lyrics that span the inspired and the crass. To include him amongst the likes of Dylan, Mitchell, and Browne isn’t an exaggeration; if anything, it’s the cold, hard truth.

Tricky though a task this is, in paying tribute to a wordsmith as great as Warren Zevon, all one can do is make marginal choices of lyrics that reflect the musician’s caustically genuine view of life. The songs below are but a few of many measures of this great man’s incredible way of wringing words out of inkwells.

10. “For My Next Trick I’ll Need a Volunteer” (Life’ll Kill Ya, 2000)

Zevon’s two 1990s albums — Mr. Bad Example and Mutineer — were not received warmly by critics or by fans, at least judging by the paltry sales of each. (This fate was undeserved for the former and fairly justified for the latter, Zevon’s weakest career effort.) After signing to the small independent label Artemis, however, Zevon came back in full force with Life’ll Kill Ya just after the century had turned, producing some of his most gutsy and forward work yet. (See the title-says-it-all, “My Shit’s Fucked Up”.) The record’s strongest moment, a classic Zevon balance of vulnerability, hilarity, and mordant wit. He opens with a classic magic show refrain: “I can saw a woman in two.” He’s not a master illusionist, though, as he reveals his weakness a breath later: “But you won’t want to look in the box when I’m through.”

The portrait of Zevon as a droopy dog, unable to do anything to impress anyone, is pervasive throughout the song: “Put me in chains / And I will escape / Better not wait up / ‘Cause it might be late.” Yet his follies are not wrought out of a world unwilling to be entertained by his antics, but rather his own conniving. “It’s lonely out here when the tricks have been played”, he muses. He has gone too far in his deceiving, which he realizes upon admitting, “And there’s no magic spell / For a broken heart.” With only three years left to Zevon’s name — a fact unknown by him at this point — many of the songs on the aptly titled Life’ll Kill Ya read as something like parting words to those he’s wronged, though it would of course be out of character for his apology to be as sarcastic as it is genuine. Failed though he might have been as a magician, he never ceased to wow the crowds even when he stumbled.

9. “Nobody’s in Love This Year” (Transverse City, 1989)

Literate techno paranoia defines Transverse City, Zevon’s cyberpunk-inspired late 1980s release. The title track depicts the technological progression of the Reagan era as resulting in a society where “life is cheap and death is free”. Once the bulk of the album’s 11 tracks finishing their prophesying, Zevon takes to depicting the consequences of the increasingly digital world in “Nobody’s in Love This Year”, a song specific to Transverse City‘s time and place and yet universal in its take on people too occupied with ennui to stop drifting in and out of love.

“We keep walking away for no reason at all,” Zevon sings, “And no one says a word.” As the world’s servers continue to pile up data and data, he finds that people, when inundated with information, turn into catatonic phantoms. This trend society-wide: “And the rate of attrition for lovers like us / Is steadily on the rise / Nobody’s in love this year / Not even you and I.” The notion of love as limited by the time it’s in is one not commonly explored in many songwriters, but leave it to Zevon’s eye for the glass-half-empty to extrapolate his individual case of bad love to a universal phenomenon.

His insecurities rise to the surface as this happens: “I don’t want to be Mr. Vulnerable / I don’t want to get hurt.” The hurt of knowing what (something like) love is comes in knowing all that it costs, which he does all too well: “If you sit back and wait for our love to accrue / You’ll be waiting a long, long time.” Even though Zevon went on to write a few more love songs before his time ended — not all of them cynical — the detached lovers of “Nobody’s in Love this Year” remain some of the most vivid figures in his entire lyrical body.

8. “Trouble Waiting to Happen”(Sentimental Hygiene, 1987)

The celebrity condition necessarily produces a split personality for anyone searching for fame: the person one is to the public and the person one is in private. The paradoxes and contradictions that can arise from this situation are obvious and, in the case of “Trouble Waiting to Happen”, hilarious. This song, the highlight of Zevon’s post-binge comeback LP Sentimental Hygiene, documents many of his encounters with the version of him constructed by the tabloid media in his absence from the music business. “I woke up this morning and fell out of bed / Trouble waiting to happen / Should have quit while I was ahead,” Zevon sings, slyly referencing the critical and popular high that waned following his self-titled debut and Excitable Boy.

From this rough-and-tumble morning comes a slew of facts about Zevon no one had bothered to mention to him: “I’d read things I didn’t know I’d done / It sounded like a lot of fun,” he laments, before giving the listener a little nudge: “I guess I’ve been bad or something!” He references an issue of Rolling Stone where he read that he was stuck at home by himself — a fact unbeknownst to him. Perhaps he was occupied by the perpetual conflict around him: “I turn on the news to the third World War / Opened up the paper to World War Four / Just when I thought it was safe to be bored.” Or, perhaps, it’s just that Warren Zevon was anything but a conventional celebrity.

7. “Model Citizen” (Mr. Bad Example, 1991)

Out of print for the majority of its existence, Mr. Bad Example suffered the fate of being released during Zevon’s unprolific ’90s. It’s easily the darkest of his work, with blackly comic tales like “Finishing Touches” and “Angel Dressed in Black” rising to the top of the very underrated heap. (The former includes one of his best jabs: “But I’m sick and tired / And my cock is sore.”) But nothing on this LP better captures Zevon’s acid vision better than “Model Citizen”, a scathing take on the American nuclear family.

Here he slips into the role of the domesticated house husband who has found a way to channel out his dormant rage on the sterilized environment around him. It’s not an easy task: “It’s the white man’s burden / And it weighs a ton,” he sings, but he manages to cover up his malice with the guise of the eponymous figure. “I pay my taxes when I can / Model citizen.”

The motions of the daily routine are embedded in this song’s speaker. In the first stanza, he deals with the milk delivery and goes to the grocery store — all seemingly ordinary things. By the second stanza, however, it’s become clear he views suburbia as a prison. He starts to “Torment the milkman / Terrorize the maid,” as were they baton-wielding wardens. As if that weren’t terrifying enough, he then takes it out on his kids: “Down in the basement / I’ve got a Craftsman lathe / Show it to the children / When they misbehave.”

His wife, meanwhile, is “playing canasta / With everyone in town”, unable to see the bitterness being fomented in her husband. His only escape is a drastic one: “When I feel the pressure / And I need a break / Load up the Winnebago / Drive it in the lake.” At least when he emerges from the lake, he can look forward to revving up that lathe again.

6. “Excitable Boy” (Excitable Boy, 1978)

Male psychosis and its mistreatment is a subject that sends psychologists reeling. Unsurprisingly, then, it’s not a common topic of interest in the American songwriter pantheon. Leave it to Zevon to take it head-on with the title track off his platinum LP Excitable Boy, where he approaches this deeply sensitive issue with a dose of gallows humor so strong many might not be able to stomach it.

The primary refrain of the song is a variation on the “boys will be boys” trope: “Excitable boy, they all said.” Throughout the repetition of that line, Zevon sketches an increasingly deranged portrait of a boy for whom the title “disturbed” would be an understatement. It starts off in a way one might expect an exceptionally goofy child to act: “He went down to dinner in his Sunday best / And he rubbed the pot roast all over his chest.” The boy only appears eccentric at first; but, of course, with the adults around him chalking up his episodes to “excitability”, things take a turn for the murderous quick, as neglect lets the boy’s neuroses grow exponentially. “He took little Suzie to the Junior Prom / Excitable boy, they all said / Then he raped her, killed her, then he took her home.”

By themselves, these lyrics are chilling; Zevon’s choice to write “Excitable Boy” as a doo-wop-inspired piano rocker with bright-sounding backup vocalists makes it horrifying. The story ends on terms no less terrifying: “After ten long years they let him out of the home / And he dug up her grave and built a cage with her bones.” Despite being one of the most pop-sounding things Zevon ever recorded, it’s a difficult and sophisticated ditty that’s easy to overlook. That this track is featured alongside the immensely popular “Werewolves of London” is indicative of Zevon’s disregard for the whims of popular demand. For every dance craze he tried his hand at, he couldn’t help but indulge in the morbidly, mortifyingly insightful.

5. “The French Inhaler” (Warren Zevon, 1976)

Along with witty quips, poetic insight, and a love for all things doleful, one of Zevon’s greatest skills as a songwriter is his ability to craft a compelling narrative in the framework of the rock song. His self-titled “debut” (technically preceded by Wanted Dead or Alive, though the latter is largely forgotten) features a great many of these examples, including the titular outlaws of “Frank and Jesse James” and the drug-addled drifter looking for solace in “Carmelita”. Zevon adopts the viewpoint of a pimp for “The French Inhaler”, a devastating yet sympathetic look at a woman’s descent into prostitution in the squalid streets of Los Angeles.

The piano that begins the song — one of many vesitges of Zevon’s early interest in classical composition — creates a larger-than-life regality that frames this tale of the underworld. “How are you gonna make your way in the world, woman / When you weren’t cut out for working?” he asks the woman, who came to Hollywood in order to strike it big. Fame, unfortunately, has a price: “How are you gonna get around / In this sleazy bedroom town / If you don’t put yourself up for sale?”

Unsurprisingly, it’s all downhill from there, and not just for the woman. Not long after she tries to climb her way to the top by feeding off of the lowlifes at the bottom, the pimp realizes how much of a sham his existence is, resulting in the song’s spine-tingling climax: “So I drank up all the money / Yes, I drank up all the money / With these phonies in this Hollywood bar / These friends of mine in this Hollywood bar.” The physical ruin this leaves both participants in is captured in one of Zevon’s best observations, uttered by the pimp as he watches the woman leave a client at two in the morning: “And her face looked like something death brought with him in his suitcase.” The fatalism with which Zevon depicts Los Angeles is a hallmark of his view of the city that helped shape his sound in a huge way. Sometimes, all one can say — as the wasted woman at the end of “The French Inhaler” does — is “So long, Norman.”

4. “Dirty Life and Times” (The Wind, 2003)

“Keep Me in Your Heart”, the final track of both The Wind and Zevon’s story as a songwriter, is a beautiful, tear-inducing farewell that caps off that album with a love that can only come at the end of a life. It is a song that is typically — and deservedly — listed as one of his best compositions, and it’s a standout cut on The Wind. The song’s exclusion on this list, then, will likely be to many a crime. But if there’s one song on that record that tops “Keep Me in Your Heart” in serving as a summation of this man’s career and as a caustically sweet farewell, it’s “Dirty Life and Times”. Opening with the clever line, “Somedays I feel like my shadow’s casting me”, the sense of death that looms over The Wind is firmly in place. Zevon, who immediately began work on the album following his diagnosis with mesothelioma, is very much counting time here, and he’s making every second count.

In the four minutes that comprise “Dirty Life and Times”, he covers just about every publicized facet of his career. There’s his persistent desire to avoid the commercial: “One day I came to a fork in the road / Folks, I just couldn’t go where I was told.” He then reiterates his cynical-yet-affectionate view of human nature: “It’s hard to find a girl with a heart of gold / When you’re living in a four-letter world.” And, of course, he can’t help but lay out the difficulties of the game of love: “And if she won’t love me then her sister will / She’s from Say-one-thing-and-mean-another’s-ville” leads right in to “Gets a little lonely, folks, you know what I mean / I’m looking for a woman with low self-esteem.” Lots of grievances go on this list of “Dirty Life and Times”, but, in the end, just as he is on “Keep Me in Your Heart”, Zevon is looking to reach out to those he loves: “Who’ll lay me out and ease my worried mind / While I’m winding down my dirty life and times?”

3. “Desperados Under the Eaves”(Warren Zevon, 1976)

Los Angeles is a fundamental part of the Zevon sound. Warren Zevon, the strongest of all his studio LPs, echoes with the horns of rush hour traffic and exudes the illuminated billboards of Sunset Boulevard, which all reach their crescendo in the epic “Desperados Under the Eaves”. As he softly plays the piano, Zevon recalls: “I was sitting in the Hollywood Hawaiian Hotel / I was starting into my empty coffee cup.” Far from early morning ennui, this moment ushers in a near apocalyptic take on the fate of LA: “And if California slides into the ocean / Like the mystics and statistics say it will / I predict this motel will be standing / Until I pay my bill.” His solution? “I was thinking that the gypsy wasn’t lying,” he admits: “All the salty margaritas in Los Angeles / I’m gonna drink ’em up.”

Backed by a tastefully placed string section, he then waxes Biblical: “Don’t the sun look angry through the trees / Don’t the trees look like crucified thieves / Don’t you feel like desperados under the eaves / Heaven help the one who leaves.” Where the track jumps into the realm of the transcendent, however, is when he lets the words stumble into a wordless climax: “I was sitting in the Hollywood Hawaiian Hotel / I was listening to the air conditioner hum.”

Then, fittingly, he hums, then joined by matching strings. “Look away down Gower Avenue,” he cries amidst the air conditioner’s tune. Eloquent and loquacious though Zevon was, he also knew just when to let the words stop, and the coda to “Desperados Under the Eaves” is one such instance. It’s a simple point being made: as the tectonic plates shift the Golden State toward its watery demise, all one can do is hope he can dodge his hotel bill yet again.

2. “Searching for a Heart” (Mr. Bad Example, 1991)

“Searching for a Heart” suffered an unfortunate fate in its initial LP version. Lyrically, it’s not just Zevon’s best take on the topic of love; it’s one of the truest things ever said on the subject, ever. By contrast, its music is as bland and safe as ’90s soft rock can get — the lyrics are done better justice by Don Henley’s wonderful, jazzy cover on the posthumous Enjoy Every Sandwich tribute. Nevertheless, “Searching for a Heart” is an inimitably Zevonian take on looking for that special someone.

It opens with a setting of the scene, a sort of netherworld for the unrequited lover: “Darkness in the morning / Shadows on the land / Certain individuals aren’t sticking with the plan.” The speaker knows what it is he’s looking for, and more importantly he knows what it isn’t: “They say love conquers all / You can’t start it like a car / You can’t stop it with a gun.” (Those lines are favorites of David Letterman, who Zevon called “the greatest friend [his] music ever had.”)

“They tell you love requires a little standing in line,” he says to his shadowy object of affection, “And I’ve been waiting for you lover / For a long, long time.” For now, though, he remains on the outside, not quite ready to take the plunge: “Leaving in the evening / Traveling at night / Staying inconspicuous / I’m staying out of sight.” Zevon’s style has been called “song noir” before, a tag especially true of “Searching for a Heart”. Scarred though his heart may have been, love never ceased being a target on his radar. It was a desirable target whose difficulty to obtain made it necessary to lurk in the shadows, waiting for that right moment for his guard to be let down.

The end of “Searching for a Heart” suggest something to that effect: “I’ve been searching high and low for you / Trying to track you down / Certain individuals / Have finally come around.” Zevon may have tried to emphasize the blackened part of his heart — which he did quite successfully — but he was never afraid to admit the risks he was taking to maybe, just maybe, soften it up. “Searching for a Heart” is the noir detective toeing his way into the light, finding what he had convinced himself was the very reason to keep to the darkness in the first place.

1. “Genius” (My Ride’s Here, 2002)

“Modestly titled,” Zevon joked as David Letterman introduced “Genius” during the singer’s last public appearance. Once he concluded that performance of the song, one thing was plain: to hell with modesty. In an all-too-short lifetime rife with lyrical gems, “Genius” is a crowning achievement. Released just a year before his death, the song plays out like a novel in miniature, opening with the humorous intonation: “I’ve got a bitter pot of je ne sais quoi / Guess what? I’m stirring it with a monkey’s paw.”

Zevon here addresses an ex-flame — it’s unclear whether she’s real or fictional — who has an intellect that matches his but a cunning that left him undone. “Did you light the candles? / Did you put on Kind of Blue? / Did you use that Ivy League voodoo on him too?” he asks her after seeing her walk out of a barbershop, where she was working her moves on a barber there. “He thinks he’ll be alright but he doesn’t know for sure / Like any other unindicted co-conspirator,” he observes as she walks away.

Watching her skillfully deceive her mark brings his mind to other geniuses. Mata Hari, he reminds us, “Had a house in France / Where she worked on all her secret plans / Men were falling for her sight unseen.” Also in her company is Albert Einstein, who “was a ladies man / While he was working on his universal plan / He was making out like Charlie Sheen.” As Zevon lists more and more details about the methodology of his ex-beloved’s con games, he depicts himself as someone equally as smart — but not quite capable of being able to do all that is necessary to be as conniving. Zevon’s gift for narrative is at its peak here: literate without being talky and articulate without being dry, “Genius” crafts a bitterly funny story of a man who, even at 55, still had yet to work out all of the kinks of the romantic sleight of hand.

And, even more so than the material on The Wind, the final stanza of this cut gets right at what makes Zevon so unique a voice: “Everybody needs a place to stand / And a method for their schemes and scams / If I could only get my record clean / I’d be a genius.” All of the sunglass-sporting skeletons may not have been purged from his closet when he left the world in 2003, but songs like this are an indication that he is exactly that: a genius.