Highwaymen and Highwomen - Historical Characters songs and worksheets

In 1985, an American music supergroup called The Highwaymen was created. The group consisted of four of country music's greatest legends: Willie Nelson, Kris Kristofferson, Waylon Jennings, and Johnny Cash. Their hit song the “Highwaymen,” written by Jimmy Webb pays homage to different men that have lost their lives throughout history, but they, and their stories, will live on. The group later performed a sequel song titled “American Remains.”

In 2019, after country singer Amanda Shires’s daughter asked her why there were so few female country singers on the radio, Amanda helped create a female country supergroup similar to The Highwaymen called the The Highwomen. Its current members are Amanda Shires, Brandi Carlile, Natalie Hemby, and Maren Morris, with guest appearances by Yola Carter, Sheryl Crow, and Dolly Parton. Their biggest hit has been a female version of “Highwayman” called “Highwomen” written by the same Jimmy Webb who wrote the male original. “Highwomen” pays homage to different women that have also lost their lives throughout history, but they, and their stories, will live on.

These three assignments has students use the videos, songs, and lyrics in order to analyze the 12 historical characters that are presented.