1- Musical beginnings. Jennings showed a talent for music from a very young age. He began playing the guitar when he was eight years old after his mother taught him to play “Thirty Pieces of Silver.” By the time he was 12 years old, he was performing on the local radio station. Jennings later went on to become a DJ at that same station.
2- Jennings began singing and playing on a nylon string guitar at the age of ten. At 12 years of age
3- While living in Nashville, Waylon rented an apartment with Johnny Cash.
4- Jennings was inducted into the Country Music Hall of Fame in 2001
5- In 1985, Jennings joined with USA for Africa to record “We Are the World” but he left the session due a dispute over the song’s lyrics that were to be sung in Swahili. (Ethiopians do not speak Swahili…)
6- In 1959, Waylon Jennings gave up his seat to J. P. “The Big Bopper” Richardson, who was suffering from the flu, on the ill-fated flight that crashed and killed musicians Richardson, Buddy Holly, and Ritchie Valens. He was haunted by the tragedy and the loss of his close friend, Holly.
7- After several disciplinary issues, 16-year-old Jennings dropped out of high school— oddly enough at the insistence of the superintendent.
8- Jennings’s music was characterized by his “powerful” singing voice, noted by his “rough-edged quality”, as well as his phrasing and texture
9- Escaping death. Jennings was supposed to be on the 1959 airplane flight that crashed and killed Buddy Holly, but Jennings gave up his seat. Jennings had previously worked with Holly on “Jole Blon” and “When Sin Stops.” He played bass on the songs.
10- In 1993, Jennings issued a children’s album, Cowboys, Sisters, Rascals and Dirt, featuring the song “Shooter’s Theme.” The song was a tribute to his 14 year-old son, Shooter, who went on to develop his own career in country-rock. Shooter played the role of his father in the 2005 movie, Walk the Line, the story of Johnny Cash.
11- The country singer-songwriter made a cameo in the 1985 live-action film Sesame Street Presents: Follow That Bird. He played a turkey farm truck driver who gives character Big Bird a ride. He also sings “Ain’t No Road Too Long” on the soundtrack.
12- At age 16, after several disciplinary infractions, tenth-grader Jennings was convinced to drop out of high school by the superintendent
13- Name change. Waylon Jennings was born Wayland Jennings, but his mother changed the spelling on his birth certificate to Waylon when he was young. Jennings did not like the name Waylon, he said in his autobiography, calling it “corny and hillbilly.” Despite his feelings on his name, Jennings eventually gave the same name to his son.
14- Waylon was the narrator of The Dukes of Hazzard and also composed/sang the show’s theme song “Good Ol’ Boys.”
15- Jennings performed some of the hand claps on Buddy Holly’s tune “You’re the One.”
16- he was posthumously awarded the Cliffie Stone Pioneer Award by the Academy of Country Music.
17- He was the balladeer for The Dukes of Hazzard, composing and singing the show’s theme song and providing narration for the show
18- Country success. In 1976, Jennings worked with Willie Nelson, his wife Jessi Colter, and Tompall Glaser to release Wanted: The Outlaws. The record became the first country album to go platinum.
19- During his hospitalization, Waylon grew a beard and was convinced to keep it to match the image of Outlaw Country.
20- Waylon was fired as a radio DJ after he played two Little Richard records in a row during his program
21- In 1972, Jennings was hospitalized with hepatitis and considered retiring from music permanently since he was also fed up with the music industry.
22- He was also recognized for his “spanky-twang” guitar style. To create his sound, he used a pronounced ‘phaser’ effect (see ‘Modulation Effects’: below) plus a mixture of thumb and fingers during the rhythmic parts, while using picks for the lead runs
23- In the mid-1980s, Johnny Cash, Kris Kristofferson, Nelson, and Jennings formed a successful group called The Highwaymen.
24- Jennings was married four times, and had six children
25- It’s impossible to think about country music outlaws without thinking of Waylon Jennings.
Sources:
“https://countryfancast.com/waylon-jennings-facts-trivia/”
https://www.axs.com/5-things-you-didn-t-know-about-waylon-jennings-52801
http://www.wiki-zero.com/index.php?q=aHR0cHM6Ly9lbi53aWtpcGVkaWEub3JnL3dpa2kvV2F5bG9uX0plbm5pbmdz