The tale of Roland is a horror movie compressed into one three-and-a-half minute song.
It tells the story of Roland, a Norwegian mercenary fighting in the Kisangani Mutinies that followed the civil war in the Congo. He's betrayed and killed by another mercenary named Van Owen but becomes a phantom who sets out to avenge his death. After gunning Van Owen down in a barroom in Mombasa, Roland continues stalking through the night, taking part in, or perhaps precipitating, armed conflicts throughout the 20th century, including Ireland, Lebanon, Palestine, and Berkeley.
In the song's final line, it's suggested that the titular vengeful wandering phantom inspired inspired heiress Patty Hearst to take up arms in support of the terrorist organisation that kidnapped her.
To suggest that the bloodshed of the mid-twentieth century was the work of a malevolent supernatural force is the kind of satire that defines some of the nest horror stories. But then, Warren Zevon was one of the smartest songwriters there ever was. Several of his songs were stories that were cinematic in scope, including "Desperados Under The Eaves," "Lawyers, Guns, and Money," and "Mama Couldn't Be Persuaded." Zevon's big hit, "Werewolves of London" is a surrealistic tale riffing on a classic horror movie.
"Roland The Headless Thompson Gunner" is a chilling story song
Bob Dylan, a man also considered among history's greatest songwriters has nothing but praise for Zevon. Dylan devoted an entire chapter of his new book, The Philosophy of Modern Song to Zevon's 2003 tune “Dirty Life and Times.”
Incredibly, "Roland" was co-written by David Lindell, an actual former mercenary who carried a business card listing him as a "guerrilla soldier and mercenary" ...among other occupations. Lindell had apparently fought in Africa, but when Zevon came across him, he was running an Irish bar in Spain.
Another of Zevon's admirers was talk show host David Letterman. In 2002, shortly after Zevon was diagnosed with terminal lung cancer, he appeared on Letterman's show and revealed his diagnosis to the world. He closed out the show by performing "Roland." It was Zevon's last ever public appearance, thus the gory tale was the last song Zevon ever played before an audience.