11. Waylon Jennings
Image Source: Clayton Call/GETTY Images
There’s no mistaking the soulful vocals of the all-time great Jennings. The rockabilly stud left high school at the age of 16, embarking on one of the more interesting journeys for a musical star of his time. In 1976, Jennings – along with country stars Willie Nelson, Tompall Glaser, and Jessi Coulter – recorded an album titled Wanted! The Outlaws which became country music’s first ever Platinum record.