I Wish Buddy Holly Released More Bad Music
Chris Dalla Riva
65 years ago this week, Buddy Holly died in a plane crash that also took the lives of Richie Valens, The Big Bopper, and Roger Peterson. Today, we revisit that tragedy.
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Last week, was the 65th anniversary of Buddy Holly’s death. I want to talk a bit about the tragedy of dying young this week. But before I get to that, I want to remind everybody that each month we do a mailbag edition of this newsletter where I answer reader questions. The next mailbag is coming up in a few weeks. Click the button below to ask that nagging musical question. If your question is selected, you get free access to this newsletter’s paid content for a month.

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The Winter Dance Party Gone Awry

When you look at Buddy Holly’s discography, it’s hard not to be astounded. If you asked me to select a perfect rock n’ roll song, I’d happily point to his song “That’ll Be the Day”. If you asked me to select a perfect melody, I’d happily point to his song “Everyday”. If you asked me to select a perfect vocal, I’d happily point to his song “True Love Ways”. I could go on and on about Buddy Holly. But what’s crazy is that he created all of this perfection before he turned 23.

Buddy Holly died tragically in a plane crash on February 3, 1959 that also took the lives of two other burgeoning stars, The Big Bopper and Richie Valens, along with the pilot, Roger Peterson. The group was on a short midwestern tour called the Winter Dance Party. When you look at how this tour was organized, you’ll see why they quickly ran into issues.

The tour sought to play 24 shows in 24 days. That alone would make it taxing on the artists. But it’s almost like the promoters organized the tour in such a way to make it as chaotic as possible. For example, the tour was supposed to play in Dubuque, Iowa on February 10, Louisville, Kentucky on February 11, and Canton, Ohio on February 12. That’s over 800 miles in three days. When you consider that this was before the completion of the interstate highway system, that every musician shared a single bus, and that there was no road crew, so the artists had to load and unload their equipment each night, you’ll see how this tour was not set up for success. And it didn’t stop there.

The tour bus was ill-equipped, frequently breaking down in the freezing cold. After a few days on the road, The Big Bopper and Richie Valens were experiencing flu-like symptoms and Holly’s drummer Carl Brunch was hospitalized with frostbite. Everyone was fed up. Holly decided that they would charter a plane to the next show. This was the plane that would crash near Clear Lake, Iowa and kill everyone onboard.

The deaths of Buddy Holly, The Big Bopper, Richie Valens, and Roger Peterson were an undoubted tragedy. But there are details about the story — details about who else could have died — that always remind me of the seeming randomness of the universe.

Dion DiMucci and his backing group The Belmonts were also part of the Winter Dance Party. Had Dion been on the flight, he would have died a minor musician from the 1950s, not the Rock n’ Roll Hall of Famer that gave us such classics as “The Wanderer”, “Runaround Sue”, and “Abraham, Martin and John”.

The band that Holly assembled for the tour also included Waylon Jennings on bass. Had Jennings been on the plane, he would have died a nameless bassist rather than a country music legend who scored 51 top ten hits on Billboard’s country charts.