Jennings was born in Littlefield, Texas, and began playing guitar at an early age. He was influenced by a variety of musical styles, including country, rock and roll, and blues. Jennings moved to Phoenix, Arizona, in the 1950s, where he began performing in local nightclubs. He eventually formed a band called the Waylors, and they released their first album in 1966.
Jennings' breakthrough album came in 1968, with the release of "Just to Satisfy You". The album was a commercial success, and it helped to establish Jennings as one of the leading figures in outlaw country music. Jennings continued to release successful albums throughout the 1970s and 1980s, including "Ladies Love Outlaws" (1972), "Wanted: The Outlaws" (1976), and "Honky Tonk Heroes" (1983).
In addition to his music, Jennings was also known for his wild and rebellious lifestyle. He was often arrested for drug possession and other offenses, and he was once sentenced to prison. However, Jennings never let his troubles keep him from making music. He continued to record and perform until his death in 2002.
Jennings was inducted into the Country Music Hall of Fame in 2001, and he has also been honored with a star on the Hollywood Walk of Fame. He is considered one of the most influential figures in country music, and his music continues to be enjoyed by fans around the world.