Austin: Willie Nelson and the American Outlaw

Essential Question

What does it mean to be an “outlaw” in the American imagination, and how did Willie Nelson represent that image?


What do deadly gunfighters, notorious bank robbers, rogue sheriffs, secret spies, polarizing activists, nonconforming artists, and the Founding Fathers of the United States have in common? All could be considered outlaws, despised by some for breaking with established rules and norms, yet admired by others for the same reason.

The outlaw is an essential character in the American story. From the earliest settlers, to the leaders of the Revolution, to the fortune-seeking adventurers who pushed America’s boundaries westward, the American allegiance to Constitution and democratic governance has often been juxtaposed with the love of a rebel’s individualistic spirit. Many Americans are proud of the systematic checks and balances within their well-ordered government, but romanticize the notion of breaking away to live life on one’s own terms regardless of the consequences.

In American popular culture, the most notorious outlaws come mostly from the “Wild West,” the lands west of the Mississippi River that were just becoming settled in the mid-19th century. From Kansas to California, communities sprung up without the structure, or protections, civil institutions provide. There, archetypal “Wild West” rogues like Jesse James and “Wild” Bill Hickok, who are among the several outlaws featured in this lesson, pursued financial gain and self-preservation by any means necessary. Though they often acted selfishly and died violently, the outlaws of the “Wild West” era retain popularity as a symbol of the liberated individual.

The West is no longer so wild. Yet, the mystique of the outlaw persists in popular culture, and musicians across genres continue to adopt the image of the outlaw as part of their personae. 

Willie Nelson tried to live within the mold of Country music and Southern life. He spent the late 1950s and entire 1960s mostly in Nashville, where he wrote and recorded songs. Nelson achieved a modicum of success, but by 1970, his career was in a rut. Looking for inspiration, he left Nashville and returned to his home state of Texas, settling in Austin. Nelson found his niche in the diverse Austin music scene, uniquely positioning himself between Country music and hippy-influenced Rock. By embracing these seemingly disparate genres Nelson created a new subgenre: Outlaw Country.

Outlaw Country is not only defined by its sound–its mere location outside of the Country music capital Nashville marked it as rogue as well. Nelson later formed The Highwaymen, a supergroup that included other country music artists associated with an “outlaw” approach to their craft and careers: Kris Kristofferson, Johnny Cash, and Waylon Jennings. Nelson’s songs and freewheeling live performances veered far from the conservative aesthetic of much of the Country music being created in Nashville. Nelson, in a sense, became an outlaw, making music that seemed to buck the rules and regulations of his industry. And his popularity only increased. 

In this lesson, students explore the concept of the outlaw through clips from Sonic Highways and images of Nelson’s work during the early outlaw period. Students will consider the idea of the outlaw as part of American identity more broadly, learning about a series of famous individuals that lived outside of the law, for either good or bad reasons.   

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Upon completion of this lesson, students will:

  1. Know (knowledge):
    • About the role the outlaw figure plays in American identity, and how the term’s use depends on context and perception
    • About several famous American outlaws
    • About Willie Nelson’s unique career as a country music artist
    • How Willie Nelson’s outlaw approach to his career had a profound influence on the Country music industry
  2. Mastery Objective:
    • Through analysis of text and images, students will be able to position the concept of the outlaw within American culture, and explain how Willie Nelson used the outlaw image to further his career.


Motivational Activity:

  1. Use a whiparound technique to ask each student to name someone they think of as an ‘outlaw.’ Record their answers on the board

  2. Show Slide 1, “Definitions of Outlaw.” Ask students:
    • Which one of the two definitions do you think defines the person you named?
    • Is the individual you chose typically revered or despised?
    • Do you think everyone agrees about the person, or different people might view your “outlaw” in varied ways? Why might that be the case?


  1. Organize the classroom into small groups for a research activity utilizing the – Resources page. (Depending on classroom internet access and the availability of electronic devices, the activity may require printing all images and research content.)
  2. Break the class into six groups. Either print and distribute, or have each group access Handout 1: Outlaws – Heroic Figures or Despised Villains?. Have each group research one of the six outlaws, respond to the Handout questions, and present their responses to the class.
  3. Tell students that you’ll now explore the career of a Country musician who has embraced the image of an “outlaw.” Display Slide 1, “Willie Nelson USA.” Ask students:
    • What symbols do you see in this image? What do these symbol “say” to you? Why? (Students will mention the flag, encourage them to also consider the artist’s hair, instrument, etc.)
    • What kind of music do you think this person might perform? Why? (Explain to students that the person pictured is Country music songwriter Willie Nelson)
    • In what ways do you think Willie Nelson might represent or transcend stereotypes of Country music in this image?
    • Do you think the image is trying to express a point of view or make a statement? Why?
  4. Play Clip 1, “Austin Music Scene Takes Shape.” Ask students:
    • Recalling the definitions of “outlaw,” in what ways might Willie Nelson have behaved like one? (Encourage students to reference the definition and consider his move away from the center of the Nashville recording industry, his decision to wear his hair long, his embrace of the seemingly separate categories of “rednecks” and “hippies.”)
    • Why do you think people might have responded more positively to Nelson’s new “outlaw” persona and sound than they did to his previous Nashville work?
    • Why do you think an “outlaw” like Nelson might choose to wrap himself in the American flag? What might it represent to him? How do you feel about connections between the dominant symbol of the U.S. and “outlaw” music being combined?
  5. Display Slide 2, “The Outlaws,” the cover of the 1976 compilation album “The Outlaws” that was specifically curated and released by RCA records to capitalize on what had become the financially lucrative Outlaw Country music trend. Ask students:
    • What visual symbols of the “outlaw” do you see on this album cover?
    • Why do you think the musicians and record label might have chosen to brand themselves as “The Outlaws”?
    • What similarities might exist between a touring musician and the idealized notion of the American outlaw?

Summary Activity:

  1. Ask students:
    • Do you think there are actual similarities between Willie Nelson and any of the six “outlaws” from your earlier research?
    • In what ways do you think the legend of an “outlaw” is woven into the fabric and history of American culture?
    • Can you think of any current artists that embrace an “outlaw” image? Who? How? Why do you think artists choose to do so?

Extension Activity:

  1. Counterculture Country Outlaw: Ask students to write a one page essay explaining the possible contradictions between the definition of an “outlaw” and Willie Nelson’s persona as the founder of “Outlaw Country” music. Students will need to research Nelson’s background and history with the Country music industry. Students must provide specific examples regarding the definition of an outlaw, Nelson’s career, and the Country music industry in their essays.


Common Core State Standards

College and Career Readiness Anchor Standards for Reading (K-12)

Reading 1: Read closely to determine what the text says explicitly and to make logical inferences from it; cite specific textual evidence when writing or speaking to support conclusions drawn from the text.

Reading 6: Assess how point of view or purpose shapes the content and style of a text.

Reading 8: Delineate and evaluate the argument and specific claims in a text, including the validity of the reasoning as well as the relevance and sufficiency of the evidence.

Reading 9: Analyze how two or more texts address similar themes or topics in order to build knowledge or to compare the approaches the authors take.

College and Career Readiness Anchor Standards for Writing (K-12)

Writing 1: Write arguments to support claims in an analysis of substantive topics or texts using valid reasoning and relevant and sufficient evidence.

Writing 7: Conduct short as well as more sustained research projects based on focused questions, demonstrating understanding of the subject under investigation.

Writing 9: Draw evidence from literary or informational texts to support analysis, reflection, and research.

College and Career Readiness Anchor Standards for Speaking and Listening (K-12)

Speaking and Listening 1: Prepare for and participate effectively in a range of conversations and collaborations with diverse partners, building on others’ ideas and expressing their own clearly and persuasively.

Speaking and Listening 2: Integrate and evaluate information presented in diverse media and formats, including visually, quantitatively, and orally.

National Curriculum Standards for Social Studies – National Council for the Social Studies (NCSS)

  • Theme 1: Culture
  • Theme 2: Time, Continuity, and Change
  • Theme 4: Individual Development and Identity
  • Theme 5: Individuals, Groups, and Institutions
  • Theme 9: Global Connections

National Standards for Music Education – National Association for Music Education (NAfME)

Core Music Standard: Responding

  • Analyze: Analyze how the structure and context of varied musical works inform the response.
  • Interpret: Support interpretations of musical works that reflect creators’ and/or performers’ expressive intent.
  • Evaluate: Support evaluations of musical works and performances based on analysis, interpretation, and established criteria.

Core Music Standard: Connecting

  • Connecting 11: Relate musical ideas and works to varied contexts and daily life to deepen understanding.