The Wisdom That Waylon Jennings Shared with Reba McEntire After Her Band Died in a Plane Crash

by Clayton Edwards

In the early morning hours of March 16th, 1991, Reba McEntire experienced a heartbreaking tragedy. A plane carrying seven of her band members as well as her tour manager crashed into the side of Otay Mountain in San Diego, California. All eight members of Reba’s team along with the pilot and co-pilot perished in the crash. Reba, her husband, and other members of her team decided not to travel that night. Not long after the news reached the public, Waylon Jennings reached out to Reba to share some words of wisdom to help her deal with the loss and any guilt she was feeling.

In a 1995 appearance on Ralph Emery on the Record, Waylon Jennings discussed what he told Reba McEntire and the tragedy he experienced that led him to reach out to the country music icon.

Waylon Jennings Understood Reba McEntire’s Pain

In February of 1959, Waylon Jennings was on the Winter Dance Party Tour with Buddy Holly, the Big Bopper, and other early rock & roll stars. Early in that tour, Holly, the Big Bopper, and Ritchie Valens died in a plane crash in what has come to be known as The Day the Music Died. Waylon was nearly on that ill-fated plane.

However, the Big Bopper had a case of the flu and the tour bus was cold. Additionally, he said that the bus would be uncomfortable for a man of his size. He offered to take Waylon Jennings’ laundry with him and clean it in exchange for his seat on the plane. Waylon agreed.

Before taking off, Buddy Holly asked Waylon to grab him a couple of hotdogs for the flight. Then, Holly asked, “You’re not coming with us?” Jennings said he wasn’t. Jokingly, the rocker told Waylon, “I hope your ol’ bus freezes up.” The future Outlaw Country pioneer replied with his own joke. During the interview with Ralph Emery, Waylon Jennings recalled, “I said to him, ‘I hope your ol’ plane crashes.’ That took me a long time to get over that.”

Some time later, a Lubbock, Texas disc jockey called Hi-Pockets sat Waylon Jennings down for a serious talk. Waylon recalled that the DJ asked him, “If you could bring Buddy back, would you?” Of course, Waylon said he would. Then, his friend and fellow Texan replied, “Well, do it. If you think you had anything to do with sending him away, you should be able to bring him back.”

Waylon Reaches Out to Reba

Waylon Jennings recalled, “He had to get it down on that level to work with me with it.”

 He went on to say that he called Reba McEntire when he heard about the plane crash. Waylon said he told her, “You’re going to go through something that there’s no way around. You’re going to blame yourself. You ain’t got nothing to do with it. You can’t bring them back and you didn’t send them out.”