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The word highwayman is first known to be used in the year 1617; other euphemisms included "knights of the road" and "gentlemen of the road." In the 19th-century American West, highwaymen were known as road agents. In the same time period in Australia, they were known as bushrangers.

Some robbed individually, but others operated in pairs or in small gangs. They often attacked coaches for their lack of protection, including public stagecoaches; the postboys who carried the mail were also frequently held up. The famous demand to "Stand and deliver!" (sometimes in forms such as "Stand and deliver your purse!" "Stand and deliver your money!" or "give me either your money or your life!") was in use from the 17th century.

The phrase "Your money or your life" is mentioned in trial reports from the mid-18th century:

There is a long history of treating highway robbers as heroes. Originally they were admired by many as bold men who confronted their victims face-to-face and were ready to fight for what they wanted. The most famous English robber hero is the legendary medieval outlaw Robin Hood. Later robber heroes included the Cavalier highwayman James Hind, the French-born gentleman highwayman Claude Du Vall, John Nevison, Dick Turpin, Sixteen String Jack, the Slovak Juraj Jánošík, and quite a few Indians including Kayamkulam Kochunni, Veerappan and Phoolan Devi.

Kristoffer Kristian "Kris" Kristofferson (born June 22, 1936) is an American musician, actor, and writer. He is known for such hits as "Me and Bobby McGee", "For the Good Times", "Sunday Mornin' Comin' Down", and "Help Me Make It Through the Night". Kristofferson is the sole writer of most of his songs, and he has collaborated with various other figures of the Nashville scene such as Shel Silverstein.

Kristoffer Kristofferson was born in Brownsville, Texas, to Mary Ann (née Ashbrook) and Lars Henry Kristofferson, a U.S. Army Air Corps officer (later a U.S. Air Force Major General). His paternal grandparents immigrated from Sweden, and Kristofferson's paternal grandfather was an officer in the Swedish Army. When Kristofferson was a child, his father pushed him toward a military career. Like most "military brats", Kristofferson moved around frequently as a youth, finally settling down in San Mateo, California, where he graduated from San Mateo High School. An aspiring writer, Kristofferson enrolled in Pomona College in 1954. He experienced his first dose of fame when he appeared in Sports Illustrated's "Faces in the Crowd" for his achievements in collegiate rugby union, football, and track and field. He and fellow classmates revived the Claremont Colleges Rugby Club in 1958, which has remained a Southern California rugby dynasty.^{[clarification needed]} Kristofferson became a member of Kappa Delta at Pomona College, graduating in 1958 with a BA, summa cum laude in Literature. In a 2004 interview with Pomona College Magazine Kristofferson mentioned philosophy professor Frederick Sontag as an important influence in his life.

Karen Mal (born 1967 in Bristol, Connecticut) is an American singer-songwriter based in Austin, Texas. She is best known for her strikingly open, child-like voice and her poetic and somewhat didactic songwriting. She is also known in the industry as a first-call session singer with a gift for harmony. Trained in theater and voice at Long Island University, Karen worked in regional theatre in Wisconsin for several years as an actor and musical director/composer before settling in Austin, Texas to play music full-time and focus on songwriting. She has been recognized professionally for her songwriting, including Portland Songwriters Association (2002) and has been a finalist in the prestigious Kerrville New Folk competition in Kerrville, Texas (2001 and 2002). She primarily performs solo and accompanies herself in a variety of traditional acoustic guitar and mandolin styles. Her recordings have featured her own songwriting, as well as material from the traditional Irish folk canon. She also often appears on stage with other artists as a session player on mandolin, bass, guitar, and/or backing vocals.

Willie Hugh Nelson (pronounced /wɪli nɛlsən /; born April 30, 1933) is an American country music singer-songwriter, as well as an author, poet, actor, and activist. The critical success of the album Shotgun Willie (1973), combined with the critical and commercial success of Red Headed Stranger (1975) and Stardust (1978), made Nelson one of the most recognized artists in country music. He was one of the main figures of outlaw country, a subgenre of country music that developed at the end of the 1960s as a reaction to the conservative restrictions of the Nashville sound. Nelson has acted in over 30 films, co-authored several books, and has been involved in activism for the use of biofuels and the legalization of marijuana.