Waylon Jennings was one of the original outlaws. The country singer was larger than life in a lot of respects with plenty of wild stories to boot. For instance, Jennings once had the Hells Angels babysit his son.
Yes, I'm talking about the biker club, not some hip new daycare down the street. Apparently, Jennings impressed several members of the Hells Angels motorcycle gang. It got to the point where the Hells Angels would show up at his shows to watch Jennings perform. As his son Shooter tells it (via Whiskey Riff), Jennings was a bit apprehensive about the Hells Angels at first. He said, "We show up at a festival somewhere and Waylon would be like 'Oh God, here they go again.'"
However, his opinion of the gang softened over time. Jennings soon grew to trust members of the Hells Angels as much as they respected them. So he struck up a friendship with some of them. How much did Jennings trust them? Well, apparently enough to watch over the well being of his son. Waylon left Shooter in the care of some of the Hells Angels members while he went off touring. Shooter recalled what the experience was like
Waylon Jennings Let Hells Angels Babysit
He had found memories. He said, "I was literally being babysat by Hells Angels, they were very nice. This one guy Hotfoot, I remember him going to a putt putt course with me when I was a little kid."
Shooter found the experience to be fun, saying, "I remember from a very little age, I was like 'That guy was cool.' He had a cane with a skeleton on it. He gave me a Pez dispenser with a skull on it because he knew how much I loved that cane."
Meanwhile, Hells Angels also ended up performing security for Jennings at several of his shows. Jennings was something else.
"Hell's Angels used to do security for Waylon Jennings," Tommy Townsend said of meeting Jennings. "My mom and dad were telling one of the guys that I liked Waylon and he said, 'Bring Tommy down here to the gate after the show and we'll let him meet him.' I remember going on the bus and talking to him for 20-30 minutes. He was asking me questions about playing music and he was as nice as he could be, made me feel right at home."
