3 Outlaw Country Songs That Still Give Me Goosebumps Decades Later

On paper, outlaw country songs should be about breaking rules, throwing a middle finger to the establishment, and being lonesome, ornery, and mean. But even outlaws get their hearts broken—or leave behind a trail of broken hearts anyway. And no matter how many times I’ve listened to these outlaw country songs, they still give me goosebumps.

Videos by American Songwriter

“Mama Tried” by Merle Haggard

Merle Haggard, more than any singer associated with outlaw country, understood as a young man what it meant to live one’s life outside the law. The country legend had been in and out of incarceration countless times, which included, reportedly, 17 escapes. When he landed behind the inescapably tall walls of San Quentin Prison, Haggard settled in and ran a series of schemes as a prisoner. Then a Johnny Cash concert at the prison inspired Haggard, and in a few years, he began his own music career. “Mama Tried” details the pain his mother must have felt as Haggard became “The one and only rebel child / From a family meek and mild.”

“Hurt” by Johnny Cash

Trent Reznor hadn’t turned 30 by the time he released The Downward Spiral. As the title of Reznor’s masterpiece suggests, this is the work of an artist sinking into a hopeless abyss. To further make the point, Nine Inch Nails supported the album on the Self Destruct Tour. With Johnny Cash’s 2002 cover, Reznor’s bleak and glitching ballad becomes an eternal hymn. This is Cash at the end of his life, glimpsing memories, a flood of good and bad, regret, pain, love, joy, loss, sorrow, and grief.

Perhaps you don’t hear the good, the love, or the joy in “Hurt”. But it’s all right there in front of you. It’s why we feel the sting of their opposites.

“Blue Eyes Crying In The Rain” by Willie Nelson

Written by Fred Rose, “Blue Eyes Crying In The Rain” has been recorded by Roy Acuff, Hank Williams, Conway Twitty, and Elvis Presley. But Willie Nelson’s forlorn reading may be the most definitive. It appears on Nelson’s landmark album, Red Headed Stranger, which cemented his outlaw legacy after Columbia Records nearly rejected it due to its sparse production. “Blue Eyes Crying In The Rain” features Nelson as a heartbroken narrator whose love fades “like a dying ember.” Alone with his tattered and scarred guitar, Trigger, you can imagine Nelson repeating this tale as he and his sidekick amble down some lonesome dirt road.

Photo Scott Gries/Getty Images