Johnny Cash often clashed with the police, and he was arrested seven different times for misdemeanor incidents such as public drunkenness, reckless driving, and drug possession between the years 1959 and 1968.
In 1965, he was arrested in Mississippi for trespassing onto private property at 2 a.m., apparently to pick flowers, and kicked his cell door so hard that he broke his toe. According to Rolling Stone, Cash based his song "Starkville City Jail" on the encounter. That same year, he was arrested for smuggling prescription drugs (stimulants) in his guitar case while crossing the border to Mexico. The famous photograph of him being led away in handcuffs further instilled his rebellious persona into the American zeitgeist (via Biography).
However, despite his romanticized outlaw image, Cash only spent a few nights in jail for his arrests and never saw prison himself (via Prison Insight). In his autobiography, the legendary country singer recalls another arrest and subsequent night in a jail cell in Nevada, where he was roomed with an intimidating lumberjack who refused to believe he was sharing a cell with Cash. The "Ring of Fire" singer attempted to calm his roommate down by singing his biggest hits, although the lumberjack never changed his mind (via Biography).
Although Cash was never a convicted felon, his tumultuous arrest record led to an appeal to prison culture that is largely responsible for his success as an artist in today's history.
If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).