Both Cash and Jennings have plenty of iconic pictures that were taken of them over the years, though I’d be willing to stick my neck out and say that this one from 1987 could be the best.
Does the picture show them hanging out backstage? Nope.
Does the photo feature Waylon and Johnny bringing the house down during a concert? It does not.
How about a still shot of the two country music legends lacing up some neon pink and green skates at a good old fashioned skating rink? Yep, that’s the one.
Now you might be asking why two of outlaw country’s biggest names would spend a night out on the town by visiting a skating rink, and I’ll confront that thought with another question: why not? It turns out that there is a pretty reasonable explanation as to why Waylon and Johnny were joining in on the skating rink fad of the 1980s, and it has to do with Waylon’s son Shooter Jennings.
Shooter said in an interview with Channel Guide Magazine that the skating rink was actually rented out for a party for him and his friends:
“When I was 4 or 5 is when The Highwaymen formed, so from a young age Cash’s family, Willie Nelson’s family, Kris’ family and our family were out on the road traveling together and doing these overseas tours, so our families bonded.
Cash threw a roller-skating party for me and my friends at the Hendersonville skating rink. There’s a picture of my dad and him lacing up their roller skates. It’s pretty funny, bright neon pink and green roller skates.”
You’ll have to use your imagination for the bright colored skates, since the picture of the two country legends lacing them up is in black and white. It looks to me like Johnny probably had the green ones, and Waylon laced up the neon pink pair.