He’s a native of Little Field, Texas.
Born Wayland Arnold Jennings on June 15, 1937, the country legend started strumming the guitar by the time he was eight – thanks to his mother, who taught him to play the instrument with the tune “Thirty Pieces of Silver.” When he was twelve years old, he was already a DJ for a local radio station, and soon after that, he formed his first band. His early influences included Bob Wills, Ernest Tubb, Hank Williams, and Elvis Presley.
He dropped out of high school.
At age 16, Jennings dropped out of Littlefield High School after several disciplinary infractions. He then took a series of odd jobs – including working with his father in the family store – while focusing on his music career.
He was roommates with Johnny Cash.
While living in Nashville in 1966, Jennings shared a one-bedroom apartment in the Madison Apartments with Johnny Cash. In an interview, Jennings even claimed that he did the cleaning at their shared apartment.
He escaped a fatal plane crash.
In 1959, a young Jennings – playing bass in Buddy Holly’s backing band for the “Winter Dance Party” tour – gave up his seat on the plane to a sick J.P. “Big Bopper” Richardson. Little did he know it would change his life forever! The plane went down, killing Holly, Richardson, and Richie Valens. It’s now known as “the day the music died.”
He almost gave up music after he contracted hepatitis.
Indeed, Jennings had his fair share of hard living. In 1972, the country legend was diagnosed with a bad case of hepatitis that needed time for hospitalization. Afflicted by disease and frustrated with the Nashville music industry, Jennings has considered retirement.
He had a major cocaine addiction.
Jennings’ heavy drug use was never a secret. His son Terry Jennings even wrote in his autobiography that his father would spend $1,500 every day on cocaine – and it wasn’t that way for a short period of time. His addiction became very public knowledge in 1977 when the authorities raided a Nashville recording studio after receiving a tip about a package that contained cocaine had been mailed to Jennings. He was arrested for cocaine possession with intent to distribute.
He once performed on the Sesame Street TV series.
Jennings showed his gentler side when he appeared in the Sesame Street musical comedy, Follow That Bird. He played the role of a turkey-truck driver and sang a duet “Ain’t No Road Too Long” as a duet with Big Bird.
There’s definitely no shortage of crazy stories in Waylon Jennings’ history.