By the mid-sixties the counterculture was seeping into country music. To understand the strangeness of this convergence, one must realize that mid-sixties country music, to the typical Eastern intellectual, could not have seemed more retrograde. Most country singers supported the Vietnam War (Johnny Cash, always a musical and political renegade, was one exception), patriarchy (Tammy Wynette’s “Stand by Your Man”), truck drivers, and Richard Nixon. Hippie bashing was a favorite pastime of Nashville songwriters. But in 1966 Bob Dylan, attracted by the city’s top-notch musicians and desperately trying to exit publicity’s glare, began recording his folk-rock music in Nashville. Two years later he made Nashville Skyline : out-and-out country music (Dylan had always been a Hank Williams fan anyway). In the late sixties Dylan’s influence among musicians and the hip intelligentsia was immense. When he called George Jones’s “Small Time Laboring Man” his favorite song of 1968 in a Rolling Stone interview, left-wing intellectuals—though George Jones was as exotic to them as Balinese gamelan music—gamely started listening to the Possum. And hard as it was for them to get past Merle Haggard’s jingoistic veneer, if Bob dug him . . . and pot-smoking lefties discovered Haggard’s rough magic.

A dissolute Florida orange-grove heir and Harvard drop-out named Gram Parsons was the first member of the counterculture to play authentic country music. Parsons was just twenty-six when he died, but through his friends —the Byrds, the Eagles, the Rolling Stones (he inspired the Stones’ “Wild Horses,” “Dead Flowers,” and “Honky Tonk Women”)—he drew thousands of rock fans to country. A writer of heartbreaking, if often unfinished-sounding, songs, Parsons made two beautiful albums, GP and Grievous Angel , and died of drugs in the California desert in 1973. His brilliance notwithstanding, his biggest contribution may have been to convert a twenty-one-year-old Joni Mitchell-style folk singer named Emmylou Harris to country music.

Gram Parsons’s impact was on his fellow rockers; he had no immediate effect on Nashville. Yet by the late sixties, a group of young Nashvillians—songwriters, mostly—were starting to flout the city’s prim social conventions, growing their hair, smoking pot, questioning the Vietnam War. Under Dylan’s and the Beatles’ influence, they rebelled musically too. Tame as it sounds today, John Hartford’s “Gentle on My Mind,” a late sixties hit for Glen Campbell, had a Whitmanesque sweep that made it a big step in Nashville’s self-liberalization. In 1970 Kris Kristofferson, an amazing fellow (Rhodes scholar, West Point instructor, failed novelist, Army helicopter pilot, and eventual Hollywood star), started placing his loose, raw-boned songs with stars like Ray Price (“For the Good Times”) and Johnny Cash (“Sunday Morning Comin’ Down”). When the rock superstar Janis Joplin cut Kristofferson’s “Me and Bobby McGee,” he became the hottest songwriter in Nashville, an antiauthoritarian smack-dab in the belly of the establishment.

Kristofferson’s success lit a fuse that hissed and popped with Waylon Jennings’s brooding early-seventies country-rock and finally exploded into the utterly improbable superstardom of Willie Nelson. A successful songwriter (“Crazy,” “Night Life,” “Funny How Time Slips Away”), an unsuccessful performer, and a closet liberal, Nelson had abandoned Nashville around 1970 for Austin, Texas. He became the hub of an Austin-Nashville coterie that called itself Outlaws—Jennings, Tompall Glaser, Jerry Jeff Walker, and others. The Outlaws’ surly machismo (which publicists quickly turned into a marketing tool) masked a serious intent: wresting control of their music from Nashville’s powerful producers. In 1972 Jennings bulled his way to a contract with RCA that gave him unprecedented artistic freedom (Chet Atkins, bested in the negotiations, complained that his own contract was more restrictive). The result, Jennings’s 1973 Honky Tonk Heroes , was a huge hit. Two years later Nelson’s Red Headed Stranger , which Columbia didn’t want to release—it sounded unfinished, it griped—was an even bigger hit. The 1976 album Wanted: The Outlaws , a slapped-together pastiche featuring Nelson and Jennings, was the first country album to sell one million copies. Nuisances no longer, Willie and Waylon were suddenly country’s ambassadors to the outside world. Every self-respecting rock fan loved the Outlaws.

Though today’s industry would loudly dissent, it makes sense to consider the generation of George Jones, Willie Nelson, and Merle Haggard the last great infusion of country-music creativity.

His 1978 album Stardust , which would stay on Billboard ’s country chart for ten solid years, the pop chart for two, brought Willie beyond rock fans to their parents; with his grizzled ponytail, bandanna, and known fondness for pot and tequila, he was Middle America’s unlikeliest icon ever. Today the Outlaws are in-laws. Waylon’s music chugs along safely, and in 1993 the sixty-year-old Willie became the youngest member of the Country Music Hall of Fame.