88. Willie Nelson
April 30th, 1933
Key Tracks "Blue EYes Crying in the Rain," "On the Road Again," "Whiskey River," "Blue Skies"
Influenced Jimmie Dale Gilmore, Ryan Adams, Lucinda Williams
Willie Nelson's secret ingredient is his unconventional phrasing — something jazz trumpeter Wynton Marsalis has described as "very unpredictable, but it comes out poetic and very logical." Dwight Yoakam calls Nelson "the most avant-garde country singer of all time." You can hear his odd phrasing and experimental use of syntax in songs ranging from early hits that he wrote for other singers such as "Hello Walls" to signature Nelson tunes like "Bloody Mary Morning." Yoakam was a teenager the first time he heard "Blue Eyes Crying in the Rain" on Casey Kasem's Top 40 countdown: "I'd never heard anything like it," Yoakam says, referring to Nelson's warm, laid-back whine and impeccably casual tone. "He's not singing to you, he's talking to you."