Willie Nelson

Willie Nelson amassed over 70 studio albums, making him more prolific than #7 George Strait by 20 albums and still releasing new music at 90. A founder of outlaw country, his 1973 'Shotgun Willie' broke from Nashville sound conventions and generated over 200 widely performed songs, including 35 number-one hits—a figure 25 chart-toppers higher than the typical artist on this list.