6 Songs That Gave Us Willie Nelson’s “Outlaw” Persona

By personifying the outlaw country’s rebellious attitude, Willie Nelson has irrevocably changed the landscape of country music. From his legendary career spanning seven decades to his support of marijuana legalization, Nelson’s music portrays a life of rebellion and adventure. His outlaw country vibe is best captured in the following six songs:

1. “Me and Paul” (1971)
This song, recorded in 1971 but released in 1985, pays tribute to Nelson’s close friend, drummer Paul English. It vividly describes the wildlife on the road, filled with escapades, unforgettable moments, and brushes with the law. Paul English, who worked alongside Nelson throughout their careers, remains a legendary figure in country music history.

2. “Whiskey River” (1973)
While Willie Nelson didn’t pen this mournful tune, his rendition transformed it into an outlaw country classic. With gritty vocals, delicate guitar work, and elements of blues and jazz, Nelson’s “Whiskey River” delves into the darkness of drowning one’s sorrows after heartbreak. Its performance on the inaugural episode of Austin City Limits solidified its place in the outlaw country canon.

3. “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” (1978)
Collaborating with Waylon Jennings, Nelson breathed new life into this cautionary tale originally recorded by Ed Bruce. Their version, featuring electric guitars, underscores the loneliness and waywardness of the cowboy lifestyle. Their grizzled vocals served as a poignant warning, and the song earned them a Grammy Award.

4. “Highwayman” (1984)
As part of The Highwaymen supergroup with Johnny Cash and Kris Kristofferson, Nelson contributed to this Grammy-winning Jimmy Webb composition. “Highwayman” weaves tales of highwaymen throughout history, their deaths merely the beginning of their stories. Nelson’s verse portrays a roadside bandit hanged for his crimes.

5. “Bloody Mary Morning” (1974)
During a challenging period in the early ’70s, Nelson contemplated leaving music. However, he rebounded with “Bloody Mary Morning,” a track from the concept album Phases and Stages. The song captures heartbreak and vitality, depicting the aimless journey fueled by alcohol after a lover’s departure. It marked a comeback for Nelson, becoming one of his signature songs.

6. “On the Road Again” (1980)
Even non-fans of Willie Nelson recognize “On the Road Again,” his signature tune that celebrates the restless spirit and love of adventure. Penned for the album Honeysuckle Rose, the song joyfully describes life on tour, embodying the freedom and excitement of a musician’s life. It earned Nelson another Grammy Award and holds a special place as the quintessential outlaw country anthem.