Waylon Jennings

One of country music's biggest stars in the 1970s and 1980s, singer-songwriter Waylon Jennings was a key figure in the outlaw country movement, which sought to break away from the polished Nashville sound to embrace a free-wheeling, counterculture sound that influenced generations of country and rock musicians. He began his career in the early 1950s, befriending fellow Texan Buddy Holly and narrowly missing the airplane crash that claimed the rock pioneer's life in 1959. Jennings struggled to gain a foothold in music during the 1960s, but gradually built his career on the strength of country-pop singles like "Only Daddy That'll Walk the Line." He broke free of the restrictive Nashville scene in the early '70s, adopting the hard rocking, hard-partying outlaw country sound personified by Willie Nelson, Tompall Glaser, and Jennings' wife, Jessi Colter. He enjoyed his greatest success in the ensuing decade, scoring No. 1 hits with "This Time" "I'm a Ramblin' Man" and the compilation album Wanted! The Outlaws, which reached the top of the pop album charts in 1976. Jennings' fiery songs and spirit inspired dozens of equally independent-minded musicians, from Dwight Yoakam and Travis Tritt to Kid Rock and his own son, Shooter Jennings. In doing so, he confirmed his status as one of country's greatest figures.