Waylon and Willie spearheaded the outlaw movement in country music, but if you separate their stylistic felonies like fiddle shunning and pigtail wearing from the real ones, what's mostly there is pill popping and tax cheating. Johnny Cash did a few nights in the cooler for drunk and disorderly, and he once started a forest fire. But he spent more time entertaining inmates than actually being one.
When Cash performed at San Quentin in the early '60s, Merle Haggard was actually there serving a 15-year sentence for a botched robbery. In fact, his whole young life was a series of juvenile detention halls, jailbreaks and robberies that make 50 Cent look like a Boy Scout. Consequently, his checkered past made his singer-songwriter approach far more compelling than the "my baby left me guess I'll drink her memory away" school, although he could excel at those, too. It's hard, after all, to separate the struggles of "If We Make It Through December" with the smoldering turmoil of "I'm a Lonesome Fugitive."
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While the trajectory of Haggard's career hardly falters, some argue his tribute albums to Western swing pioneer Bob Wills, Dixie blues and Jimmie Rodgers, which were probably holding actions while he accumulated more original songs, are among his best albums. And while his 1969 attack on hippie liberals "Okie From Muskogee" might make you think he'd have a knee-jerk reaction to the Iraqi war, he's one of the few country artists to blast the public's roasting of Dixie Chick Natalie Maines for merely speaking her mind.