The result was a collection of songs with psychedelic guitar parts and odd vocal effects that never saw the light of day.
Jennings set the project aside and forged ahead with his own career.
Now, almost seven years after his father's death, he's retooled the recordings and released them on a new CD, "Waylon Forever," billed as the late country star's final recordings.
"It's more mature," Jennings said recently of the new arrangements he added with his band, the .357s. "At the time, being 16, I think I didn't know how to embrace subtly as much."
His father sings on the eight tracks and plays guitar on two of them, "Jack of Diamonds" and "Lonesome On'ry and Mean."
The disc features remakes of Jennings classics such as "Waymore's Blues," a cover of Cream's "White Room" and a never-released Waylon Jennings composition called "I Found the Body."
The younger Jennings credits his girlfriend, Drea de Matteo, and his producer, Dave Cobb, with finally getting the CD released on Vagrant Records.
"They were pushing me, 'You know, you've got to do this,"' Jennings recalled. "It was always there, but it was always intimidating to me to go back and try to revamp it."
Until then, he said, "I wasn't in a place yet to do it. In my own music and in working with my band and with my producer, I had to get to a place where I really felt it was the right time."