Tag: Ritchie Valens

Rolling Stone photo

Twist of fate gave Waylon Jennings life — and guilt

Remembering Waylon “Hoss” Jennings, who died on February 13, 2002. He was 64.

In 1959, Waylon was a member of Buddy Holly’s band that was on a “Winter Dance Party” tour of the Midwest. Waylon and Buddy, both 22, were teen-age friends from Lubbock, Texas.

The weather in Minnesota that February night was rotten and Buddy decided to leave the tour bus and charter a small plane to get to the next venue in Moorhead, Minnesota.


The plane had room for only three passengers. It was decided that Buddy, Waylon and band member Tommy Allsup would take take the plane, but band member The Big Bopper (J.P. Richardson) had the flu and wanted to get to Moorhead as soon as he could and asked Waylon for his seat on the plane.

When Buddy was told that Waylon was not going on the plane he said to his friend in jest, “Well, I hope your ol’ bus freezes up.” And Waylon replied in jest, “Well, I hope your ol’ plane crashes.”

About an hour and a half later, around 1 a.m., the plane crashed into a cornfield outside Mason City, Iowa, killing the three musicians and the pilot.

Crash site

The casual joke haunted Waylon for the rest of his life and led to years of cocaine addiction.

In another twist of fate that night, 17-year-old band member Ritchie Valens asked Tommy Allsup for his seat on the plane. They tossed a coin to decide and Ritchie won the toss — and lost his life.

*[Backstory below]


Waylon lived another 42 years and recorded 60 albums, including sixteen country singles that topped the charts.

In the mid-1980s, he teamed up with Willie Nelson, Johnny Cash and Kris Kristofferson to form the quartet ‘The Highwaymen,’ making records and doing concert tours.

Waylon Jennings was inducted into the Country Music Hall of Fame in October 2001.


Crash site

February 3, 1959 — The Tour From Hell

Tragic plane crash

They were so young. Buddy Holly was 22, the Big Bopper was 28, and Ritchie Valens was only 17. And the pilot, Roger Peterson, whose name is forgotten, was 21.


Buddy Holly and his new band — Waylon Jennings, Tommy Allsup and Carl Bunch — were on a “Winter Dance Party” tour across the Midwest. Up-and-coming artists Ritchie Valens, the Big Bopper (J.P. Richardson) and Dion (DiMucci) and the Belmonts also joined the tour.

The musicians traveled by bus, which turned out to be five different buses because they kept breaking down and had to be replaced. The buses were not equipped for the weather, which consisted of temperatures as low as minus 36 degrees F (minus 38 degrees C) and waist-deep snow in several areas.

Because of the bitter cold, some of the musicians got the flu. Carl Bunch was even hospitalized with frostbite.


After the group had performed at Clear Lake, Iowa, Buddy Holly decided to charter a light plane, a Beechcraft Bonanza, to reach their next venue in Moorhead, Minnesota.

The plane had room for only three passengers and since the Big Bopper had the flu and wanted to get there as quickly as possible he took Waylon Jennings’ seat on the plane and Waylon stayed on the bus.

In another twist of fate, Richie Valens and Tommy Allsup tossed a coin for the remaining seat. Valens won the coin toss, saying, “This is the first time I’ve ever won anything.”

News headline

The organization that booked the tour, General Artists Corporation, reportedly showed “a total disregard for the conditions” in which the musicians travelled.

They didn’t care. The tour from hell — that’s what they named it.

— Buddy Holly historian Bill Griggs