6. The Excitable Boy, “Excitable Boy” (from Excitable Boy, 1978)
By the time he released Excitable Boy in 1978, Zevon had already set the pattern for what his best songs would sound like: a classic rock ’n’ roll sound expertly played beneath freaky little character studies, delivered with a strong dose of black humor. The album’s title track was a perfect example: the music is bouncy, with an exuberant piano riff and an almost whimsical girl-group background vocal, but the lyrics describe an unsettling progression of incidents in the life of an unhinged psychopath. At first he’s harmless, dressing up for dinner and then smearing food all over himself, but later, he moves on to attacking theater employees, and finally becomes a grisly sex murderer. The incongruity between the happy little tune and the dark content is what makes “Excitable Boy” one of Zevon’s most memorable songs, but typically, there’s a final twist: The title is actually Zevon’s nickname. In his younger years, when he asked his bandmates why they never let him take guitar solos, one of them responded, “Warren, you have good ideas, but you’re just too excitable.”

7. Roland, “Roland The Headless Thompson Gunner” (from Excitable Boy, 1978)
One of Zevon’s most enduring songs, “Roland The Headless Thompson Gunner” was penned in collaboration with bartender/ex-mercenary David Lindell. It tells a twisted little ghost story about Roland, a Norwegian machine-gunner: Roland travels with mercenaries in Africa who, the song explains with a typically Zevonian cynicism, “killed to earn their living—and to help out the Congolese.” Roland’s skill with the Thompson gun attracts negative attention from the CIA, which convinces his comrade Van Owen to blow his head off, as the song’s chorus transitions from singing the praises of “Roland the Thompson gunner” to the titular monstrosity. Exacting a horrible revenge on the treacherous Van Owen, Roland goes on to become a sort of wandering spirit of violence, appearing in a travelogue of hot spots (Ireland, Lebanon, Palestine, and Berkeley). It’s an ode to bad-assery that makes tough-talking patriotic country songs seem like weak wannabes.

8. Bill Lee, “Bill Lee” (from Bad Luck Streak In Dancing School, 1980)
It’s no surprise that Zevon would lionize legendary Boston Red Sox pitcher Bill “Spaceman” Lee, a pitcher who became a counterculture hero for his hippie-dippy attitude during one of the Sox’s greatest eras. In this short piano ballad, Zevon gets inside the mind of Lee, standing in the middle of the diamond all alone, away from the guys in the dugout who expect him to “nod at stupid things.” The song is a salute to individualism, and to the understanding that when a group demands conformity, one man can still make his own way by controlling his own performance.

9. The Gorilla, “Gorilla, You’re A Desperado” (from Bad Luck Streak In Dancing School, 1980)
In one of Zevon’s most whimsical songs, a big ape snatches the glasses off the narrator’s face, then proceeds to take over his life: stealing his car, moving into his apartment, and making his wife miserable. Later, The Gorilla gets divorced, builds a big house, goes into therapy, and feels like he’s “shackled to a platinum chain.” Any resemblance between The Gorilla and a certain cranky rock star is purely intentional.



10. Philip Habib, “The Envoy” (from The Envoy, 1982)
Although the name of the hard-nosed, multi-talented diplomat in Zevon’s 1982 song “The Envoy” is never mentioned, it’s an open secret that it was written to honor the Arab-American statesman Philip Habib. Serving under seven presidents, Habib was known for his integrity (he stood up to Ronald Reagan when ordered to aid the Contras), his toughness (he personally helped a leading Korean politician escape attackers), and his willingness to take on any project, including the seemingly unsolvable Arab-Israeli conflict. In short, he was just the kind of character that appealed to Zevon: smart, unconventional, and attracted to danger. Over a pounding beat and howling guitars, Zevon sings about how “whenever there’s a crisis, the President sends his envoy in,” and pours out a laundry list of troubled regions—Israel, Syria, and Baghdad, who “does whatever she please”— that are, sadly, just as relevant almost 30 years later.


11. Charlie, “Charlie’s Medicine” (from The Envoy, 1982)
Charlie may or may not be based on a real person; more likely, given the fatality-strewn drug lifestyle that Zevon and his Hollywood cronies lived during the 1970s, he was a composite. Over a bluesy tune that alternates between rough electrics and gentle acoustics, Zevon tells the story of a man who “dealt in pharmaceuticals” and who was recently murdered: “Some respectable doctor from Beverly Hills shot him through the heart.” Though he seems to regret ever getting involved with Charlie (“I gave Charlie all my money; what the hell was I thinking of?”), the narrator nonetheless shows up at his funeral at the behest of the dealer’s sister, and says, in the song’s final ambiguous twist, “I came to finish paying my bill.” An underrated gem off 1982’s The Envoy, “Charlie’s Medicine” is one of Zevon’s best portraits of the L.A. low life.

12. Ray ‘Boom Boom’ Mancini, “Boom Boom Mancini” (from Sentimental Hygiene, 1987)
Suitably, Zevon’s most rocking song is this punishing, two-guitar crusher about hard-punching lightweight boxer Ray “Boom Boom” Mancini. Zevon and Mancini were friends, and for his 1987 LP Sentimental Hygiene, the singer penned a tune tracking the fighter’s career. By then, Mancini was less famous for his title bouts than for his match against Korean boxer Duk Koo Kim, who died of brain injuries a few days after the two fought. While in real life, Mancini was (though blameless) stricken with remorse for his opponent’s death, Zevon gave the song an unrepentant swagger: “They made hypocrite judgments after the fact,” he snarls, “but the name of the game is be hit and hit back.” In spite of the album’s title, Zevon’s view of the sweet science was decidedly unsentimental, and the song has lived on long past the infamy of its subject, who’s now retired and working as a producer and fight consultant in Hollywood.

13. Michael Jackson, “Splendid Isolation” (from Transverse City, 1989)
This paean to loneliness begins with the narrator wishing he were like Georgia O’Keefe, all “alone in the desert,” but in the second verse, the ideal of solitude starts to turn sour, as Zevon describes “Michael Jackson in Disneyland / Don’t have to share it with nobody else / Lock the gates Goofy take my hand / And lead me through the world of self.” By the end of the song, the singer’s putting tinfoil on his windows, shutting out the pain of the world outside. It’s a slippery slope from protecting privacy to outright madness, and in “Splendid Isolation,” Jackson is on his way to the latter, and likely whistling a happy tune as he goes.

14. Mr. Bad Example, “Mr. Bad Example” (from Mr. Bad Example, 1991)
Zevon wrote and sung about countless rogues, but none rogue-ier than the hero of “Mr. Bad Example,” who boasts about stealing money from the church, conning prostitutes, exploiting the poor, and swindling the bald (a job for which “very few are chosen, and fewer still are called”). Even in his early days working in his father’s carpet store, Mr. Bad Example busies himself “laying tackless stripping, and housewives by the score.” In the end, he wraps up his adventures “none the worse for wear.” No lessons have been learned. No retribution is coming. And the song is so jaunty that it makes shameless misbehavior sound like a lot of fun. That is, so long as you aren’t one of the helpless, gullible people that Mr. Bad Example leaves in the lurch—whom Zevon makes sure to cite.

15. Bruce Springsteen, “The Indifference Of Heaven” (from Learning To Flinch, 1993)
First introduced on the 1993 acoustic live album Learning To Flinch, then reprised on the elegiac 1995 album Mutineer, “The Indifference Of Heaven” is a beautiful song about the deep ugliness that defines human existence. Yet even while Zevon’s articulating his vision of a Godless, pointless, miserable universe, he needles his buddy Bruce Springsteen (and Billy Joel to boot), singing that while his friends say “better days are near,” the truth is that, “They don’t live around here… Billy and Christie don’t… Bruce and Patti don’t… They don’t live around here.” In Zevon’s universe, optimism can’t be willed into existence—not when pessimism is so deeply rooted.


16. Elvis Presley, “Porcelain Monkey” (from Life’ll Kill Ya, 1999)
Zevon’s lifelong distaste for Elvis Presley found its way into this stinging rocker about a guy who starts out with great promise and then trades it all in “for a night in Las Vegas and his face on velveteen.” The King surrounds himself with “regicidal friends,” scarfs fried chicken, and buys useless trinkets like the title object. In a 2000 interview with the JAM! Showbiz site, Zevon said, “I’m being a little cute about it. I just don't find him very interesting. It’s extraordinary how little impulse there is to define oneself as a human being in Elvis’s life.”

17. Buddy The Hockey Player, “Hit Somebody! (The Hockey Song)” (from My Ride’s Here, 2002)
Bestselling author and sportswriter Mitch Albom collaborated with Zevon on this late-period story-song (which also features background shouts by David Letterman), about a Canadian hockey freak named Buddy who grows up wanting to be Rocket Richard, but instead becomes his team’s go-to goon, put into the game to check his opponents into unconsciousness. Finally, one night, he gets a shot on goal and ignores his orders, skating away from the fray to take his scoring opportunity. The result? He gets knocked cold by a Finnish bruiser, but the puck goes in. Which just goes to show that even if people pay their money to see some antisocial idiot put on a show, said idiot still has the option to thrill them another way.


18. The Nameless Narrator
It’d be a mistake to consider all of Zevon’s first-person songs as autobiographical, but there does seem to be a connection between all the barflies and desperate characters who tell their stories through Zevon. Whether they’re gulping down “all the salty margaritas in Los Angeles” while confronting an angry sun in “Desperadoes Under The Eaves,” or they’re partying so hard that they need “Lawyers, Guns And Money” to get out of a jam, Zevon’s nameless narrators lead 24-hour lives, spurred on by violence, chemicals, and a fear they only occasionally pause to contemplate. Zevon wrote a lot of songs that could serve as his epitaph—including the nakedly personal “Keep Me In Your Heart,” his final song on his final album—but if you’re looking for a handy way to encapsulate The Zevon Doctrine, look to a song on his self-titled album. Put aptly: “I’ll Sleep When I’m Dead.”