TDIH: "The Day the Music Died"

On this day in 1959, musicians Buddy Holly, Ritchie Valens, and J.P. Richardson (“the Big Bopper”) are killed in a plane crash. The terrible tragedy has come to be known as “the Day the Music Died.”

None of it would have occurred but for the “Tour from Hell.”

Holly, Valens, and Richardson were then on that 24-day concert tour, officially known as the Winter Dance Party Tour. Along with Dion and the Belmonts and Frankie Sardo, they would travel across Wisconsin, Minnesota, and Iowa, singing and dancing for teenage crowds, beginning on January 23, 1959, in Milwaukee.

Unfortunately, the General Artists Corporation had planned tour stops without any regard for efficiency. The musicians spent hours a day on a bus, traveling hundreds of miles to each new location, often backtracking across roads already traveled.

Making matters worse, there was no interstate as we would have today. Instead, the musicians traveled on rural roads in what was effectively an unreliable school bus.

The worst of these breakdowns came on February 1, as the bus traveled from Duluth to Green Bay. The musicians were stranded for hours in subzero temperatures, keeping themselves warm by drinking whiskey and burning newspapers in the bus aisle. They lost one drummer that day to frostbite: He had to be hospitalized after they were rescued.

By February 2, Holly was out of patience. They were then playing at the Surf Ballroom in Clear Lake, Iowa, but their next stop was hours away in Moorhead, Minnesota. He wanted to sleep. He wanted to do his laundry. He wanted a shower—all luxuries that had been hard to come by with the constant driving.

So he chartered a plane—a 1947 Beechcraft Bonanza with room for only 3 passengers. Which lucky musicians would get to go?

Dion remembers being offered a spot, but declining when he learned the $36 per passenger price tag. “[A] light went off in my head because my father paid that monthly for rent in the Bronx,” he later explained. “So I thought, ‘I’m not going to spend a whole month’s rent just for a flight.’”

Other accounts say that Holly had decided to take his band members, Allsup and Waylon Jennings, but each gave his seat away. Valens convinced Allsup to flip a coin for his seat. In the meantime, Jennings was approached by Richardson. “We were really good friends,” Jennings explained. “He said, ‘Man, I’ve been sick. I have the flu. I can’t get any rest at all. Would you mind if I take your place on the plane?’” Holly approved the plan but joked with Jennings, too.

“I hope your damned bus freezes up again,” Holly reportedly laughed. “Well, I hope your ol’ plane crashes,” Jennings teased back.

It took him years to get over the fact that he’d made that particular joke.

The weather was deteriorating, but no one seemed to realize it. The charter pilot was not certified to fly on instruments only. Worse, he received inaccurate weather reports and apparently did not realize that he should not be flying that night. 

The little plane departed Mason City at 12:55 a.m. The airport soon lost contact with the pilot, but the plane’s wreckage wasn’t found until the next morning. Everyone aboard had been killed instantly upon hitting the frozen ground.

The tragedy rocked the nation. As you know, Don McLean would even write about it in his song, American Pie, calling it the Day the Music Died.

“Those three guys affected my life on a lot of levels,” Dion later concluded. “Buddy told me once, ‘Dion, I don’t know how to succeed, but I know how to fail. Try to please everybody, and you’ll go nowhere.’ . . . I miss those guys. Thank God that in my faith, relationships never end. . . . I have three angels up there.”

Primary Sources:

• Alaina Bartel, The day the music died: How Don McLean’s ‘American Pie’ immortalized a tragedy (Case Western Reserve Newsroom; February 02, 2024)

• Eastern Iowa remembers 'The Day the Music Died' 66 years after 1959 plane crash (CBS2: Iowa’s News Now; February 2, 2026)

• Inductees: Buddy Holly (Rock & Roll Hall of Fame)

• Jack Irvin, Waylon Jennings’ Eerie Last Words to Buddy Holly Before His Death: ‘I Hope Your Ol' Plane Crashes’ (People; February 3, 2023)

• Jim Clash, Rock Icon Dion Recalls 1959 Plane Crash That Killed Buddy Holly, Ritchie Valens And The Big Bopper (Forbes; Feb. 14, 2019)

• Matthew Leimkuehler, What to know about ‘the day the music died’ and Buddy Holly’s plane crash in Iowa (Des Moines Register; Jan. 24, 2019)

• Michael Hall, The Night the Music Died: Searching for the ghost of Buddy Holly in Clear Lake, Iowa (Texas Monthly; February 2009)

• On This Day, 1959: Buddy Holly killed in air crash (BBC)

• Rob Haswell, Wisconsin's bitter cold led to crash that killed Buddy Holly on Feb. 3, 1959 (FOX6 Milwaukee; February 3, 2025)