Raisin‘ Hell

Like rappers, country artists seem to sometimes benefit from a reputation for wild, even illegal, antics. Maybe such drama inspires great songwriting—or perhaps country fans, despite their reputation as a conservative crowd, just love them an outlaw. Whatever the synergy between country music and raisin‘ hell, these 10 genre luminaries have embraced both to spectacular effect.

Hank Williams

Due in part to his constant discomfort from mild (and un-diagnosed) spina bifida, Hank Williams battled alcohol and painkiller addiction for much of his 29 years. It cost him a marriage, his early gig with Grand Ole Opry and, in 1953, his life (to a heart attack caused by a combination of morphine, chloral hydrate and booze). Yet Williams played on through (or perhaps because of) the pain, scoring 11 No. 1 hits.

Johnny Cash

“The Man in Black” never actually served a prison sentence, but his seven overnight jail stays, heavy drinking and addiction to barbiturates and amphetamines were enough to earn him an outlaw image (which he carefully cultured). Causing a 500-acre forest fire in 1965 (in fact an accident caused by his over-heated truck)—and the resulting lawsuit by the federal government—only boosted his bad boy rep.

Willie Nelson

A longtime marijuana legalization activist (a co-chair of NORML—the National Organization for the Reform of Marijuana Laws), Willie Nelson has been arrested numerous times for pot (and, on one occasion, hallucinogenic mushroom) possession. Consciously embracing outlaw country in the 1970s (as confirmed by his ’76 album Wanted! The Outlaws), Nelson maintains, even at age 78, a subversive glint in his eye.

Merle Haggard

Shoplifting from a lingerie store at age 13 set the tone for a decade of on-and-off incarceration (including a stint in San Quentin) for this pillar of the Bakersfield Sound. By the 1960s he was straightening himself out, and was even pardoned by then-California Gov. Ronald Reagan in 1972, yet Haggard will always be associated with “outlaw country.”

Loretta Lynn

Shaking up conservative country in the 1970s with songs about birth control (“The Pill”), the double standards faced by divorced women (“Rated X”) and repeated motherhood (“One’s on the Way”), Loretta Lynn may have had more records banned from radio than any other artist in the genre. But this Kentucky crooner seeks to influence rather than shun the establishment—she calls more than one former U.S. President a friend and has been a repeat guest at the White House.

Steve Earle

A high school dropout who’s been married seven times (including twice to the same woman), Steve Earle is almost as well known for his sometimes controversial activism as he is for his rock-tinged country songs. Earle has been avidly anti-war and against the death penalty for decades, and his song “John Walker’s Blues”—written from the point of view of American Taliban member John Walker Lindh—had fingers pointing and jaws jabbering.

David Allen Coe

In-and-out of correctional institutions since age 9; a one-time member of the Outlaws motorcycle club; and capable of penning disgustingly racist and misogynistic lyrics, David Allen Coe is amongst the best-qualified of outlaw country artists (though his claims of having been on Ohio’s death row appear unfounded). His hit single “Long Haired Redneck” can be assumed to be at least partly—and proudly—autobiographical.

Waylon Jennings

One of the so-called “outlaw” country musicians who shunned the corporate Nashville scene of the 1970s, Waylon Jennings was a full-blown cocaine addict by the turn of the 1980s. His famously debauched tours at the time were, ironically, sometimes performed specifically to pay off debts due in part to his drug use. Arrested for coke possession in 1977, DEA bungling spared Jennings when the agency was forced to drop the charges.

Gram Parsons

This former Byrd and Flying Burrito Brother had a taste for booze, cocaine and opiates which seems to have stunted his mid-career musical output. It was an overdose of morphine that killed him in 1973 during one of many drug-fueled excursions into Joshua Tree National Monument. His Topanga Canyon home burning down earlier that same year (thanks to a discarded cigarette) has only furthered Parsons’ wild rep.

Lucinda Williams

Kicked out of high school in 1969 for refusing to recite the Pledge of Allegiance, Lucinda Williams has for much of her career (except for the period around her gold-certified Car Wheels on a Gravel Road album in 1998) been a somewhat tortured cult artist. Destructive relationships and a famously drifting lifestyle (not to mention hard alcohol) were left in the rearview mirror when she married former music executive Tom Overby on stage in 2009. (Paul Rogers)