The name Waylon has its origins in the Old English language and can be traced back to the 9th century. It is derived from the Old English words "Wæl" meaning "foreigner" or "stranger" and "wyn" meaning "joy" or "pleasure." The name was initially used to refer to a joyful or pleasant stranger or foreigner.

One of the earliest recorded instances of the name Waylon appears in the Domesday Book, a manuscript record of a great survey of England completed in 1086 by order of King William the Conqueror. The name is mentioned as a personal name of several landholders in various parts of the country.

In the 12th century, the name Waylon was found in the medieval English romance "Amis and Amiloun," a narrative poem that tells the story of two friends whose loyalty and devotion to each other are tested. One of the main characters is named Amylion, which is believed to be a variant spelling of Waylon.

Throughout history, several notable individuals have borne the name Waylon. One of the earliest was Waylon Durvile (c. 1150-1215), an English nobleman and crusader who participated in the Third Crusade under King Richard I. Another was Waylon Wray (c. 1592-1669), an English clergyman and author who served as the chaplain to King Charles I.

In the 18th century, Waylon Jennings (1701-1772) was a prominent English architect known for his work on several churches and public buildings in London. Waylon Lamb (1835-1890) was a notable American Civil War veteran and politician who served as the 14th governor of Nevada from 1887 to 1891.

Perhaps the most famous bearer of the name Waylon was Waylon Jennings (1937-2002), the influential American country music singer and songwriter. He is widely regarded as one of the most influential and iconic figures in the history of country music, known for his distinctive bass-baritone voice and his outlaw country style.