The lyrics of "Highwayman" tell the tale of a man who has lived multiple lives as a highwayman, sailor, dam builder, and potentially a starship pilot, seemingly outliving death each time he is thought to have died.

Meaning of "Highwayman" by Jimmy Webb

"Highwayman" by Jimmy Webb represents the cyclical nature of life and the resilience of the human spirit. The protagonist's ability to reincarnate into different personas after each supposed death symbolizes the idea of constantly evolving and adapting to new circumstances. The repetition of the phrase "but I am still alive" emphasizes the enduring nature of the protagonist's essence, suggesting a form of immortality that transcends physical death. The notion of being "back again, and again" reinforces the idea of perpetual rebirth and renewal, highlighting the never-ending cycle of life and death.