Zevon met co-writer Lindell in Spain, where the latter was running a bar after a stint working as a mercenary in Africa. Always interested in the darker side of life, Zevon decided to collaborate with Lindell on a song about a mercenary.
The fictional character Roland is a Norwegian who becomes embroiled in the aftermath of the Nigerian Civil War and Congo Crisis of the 1960s - the lyrics mention the years 1966 and 1967, which correspond to the mercenary-led Kisangani Mutinies after the Congo Crisis. He earns a reputation as the greatest Thompson gunner, a reputation that attracts the attention of the CIA. Roland is betrayed and murdered by a fellow mercenary, Van Owen, who blows off his head. Roland becomes the phantom "headless Thompson gunner" and eventually has his revenge, when he catches Van Owen in a Mombasa bar and guns him down. Afterward, he continues "wandering through the night." Other violent conflicts of the succeeding decade are said to be haunted by Roland, including Ireland, Lebanon, Palestine, and Berkeley, California. At the end of the song, Patty Hearst, and her stint as Tania of the Symbionese Liberation Army (as memorialized by several photos published nationally of Hearst holding an automatic weapon) is said to have "heard the burst of Roland's Thompson gun and bought it."