| Subject: February 2, 1959 |
Author:
Randy Steele
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Date Posted: Mon February 02, 2026 23:23:58
By the time February 2nd had turned on the calendar, the 1959 Winter Dance Party Tour was on its 10th day. On paper, the tour had looked like a great idea. It would be a rock-n-roll traveling show across the Midwest, giving many teenagers their first opportunity to see some of their music idols perform in person.
The tour would feature newcomers J. P. The Big Bopper” Richardson and Frankie Sardo, a rising star in Ritchie Valens, along with a couple of well-established acts in Dion and The Belmonts and the remarkable Buddy Holly. But in any given year, January and February in the Midwest means almost everything is frozen solid. The planners for the Winter Dance Party had failed miserably in taking this fact into account.
The transportation arrangements made for the tour were not only ridiculous, but they were also downright dangerous. The artists had quickly found themselves traveling in nothing more than converted school buses in sub-zero temperatures. The hard temperatures proved to be too much strain on the buses, causing them to break down repeatedly. The breakdowns caused the boys to change buses multiple times in the first days of the tour. Tensions were running high. After a show in Duluth, Minnesota on January 31st, the guys loaded back into the bus around 11:00 p.m. to make an all-night trip into Wisconsin but the bus broke down again.
An afternoon show scheduled in Appleton, Wisconsin on February 1st had to be cancelled. Carl Bunch, Buddy Holly’s drummer on the WDP tour, had to be hospitalized with frostbite. The second show of the day, scheduled for the evening of February 1st, was to be in Green Bay, Wisconsin. By the time the stars arrived in Green Bay, the patience of everyone on the bus was either razor thin or completely gone.
Around this time, 17-year-old Ritchie Valens, the youngest act on the WDP tour, called back home to his manager Bob Keane, telling him all about the awful weather and terrible tour conditions. Keane suggested that Ritchie get on the first plane out the following day and return to California.
Buddy Holly had reportedly been on the telephone to his attorney about getting the money he believed his former manager Norman Petty owed to him. The Big Bopper had called home to speak with his wife Teetsie, who was at home pregnant with their second child. There’s something worth noting here: The Big Bopper and Buddy Holly were raised in the South. Ritchie Valens had been raised in the West. Both are warm climates and not used to blizzard-like conditions.
After the latest problem with the bus, the boys arrived in Green Bay for a show at the Riverside Ballroom. Among the kids attending the show that night was a group of four friends who were big time Buddy Holly fans…Larry Matti, his buddy Bob Oestreich, and twins Joan and Judy Bender. They traveled from Wausau, Wisconsin to Green Bay to see the show and arrived around 6:30 p.m. and caught the guys getting set up for the show. Bob had asked Buddy if they could remain backstage during the show and Buddy Holly said yes. Larry Matti had brought along his camera and captured brilliant-colored photographs of the artists backstage.
One of the Larry Matti photos that night clearly stood out among the others. It was a close-up shot of Buddy Holly sitting down on some steps, wearing his trademark look of horned-rimmed glasses. Buddy appeared to be pondering all that was taking place in front of him, perhaps wondering how and why he found himself in the middle of it. To me it is the saddest photo ever taken of Buddy Holly. He appears to be exhausted and exasperated. In that moment, Buddy is a twenty-two-year-old young man who is far from home, without his wife, his family, his friends, and without his band. Buddy Holly appears to be sad, lonely, and lost.
While tensions may have been growing amongst the artists, some of the 2,000 kids who attended the Green Bay concert that night stated that the show was simply fantastic. But a situation took place after the Green Bay show that changed everything.
After this show, the artists did not jump back onto the bus for another grueling night of wintry travel. Instead, they stayed overnight in various hotels around town, finding themselves with a hot meal, a hot bath, and best of all, a nice, warm bed all night long. According to Tommy Allsup, spending the night in normal conditions was the perfect medicine desperately needed by everyone.
I am convinced that staying overnight in a Green Bay hotel was the game changer of the Winter Dance Party.
The next morning, the singers were rested and ready but the day that lay before them would be anything but easy. The next show in Clear Lake, Iowa was a last minute add on, and almost four hundred miles away. A new bus was brought in from Chicago, but mother-nature had provided a stark reminder of the perils of a Midwest winter—the outside temperature was -19 degrees below zero. It wasn’t long before the subzero weather caused the same old problems to reappear, delaying the tour’s journey to the Surf Ballroom in Clear Lake, Iowa.
The new bus was no match for mother nature and broke down and was towed to a shop for repairs. The delay caused the bus to finally make it to Clear Lake around 6:30 p.m., causing the singers to miss a scheduled appearance at a record store in nearby Mason City and giving the acts about 90 minutes to find something to eat and to get ready for the show. By any measurement, this was the tour from hell. Worst of all, there was no end in sight to the horrendous conditions.
Buddy Holly had finally had enough. There was little question that Buddy Holly was not only a Winter Dance Party headliner, but he was also a STAR. He had traveled by car, bus, and plane around the globe and had played across America, Canada, England, and Australia. He even played in Hawaii before it was a state! The conditions were ridiculous and dangerous. Staying overnight in Green Bay convinced Buddy that things had to change and change immediately.
Once the buses arrived at the Surf Ballroom, Buddy Holly approached Surf Manager Carroll Anderson to ask if he could help arrange a charter flight to Fargo, North Dakota after the show for himself, Tommy Allsup, and Waylon Jennings. By Buddy’s way of thinking, arriving early would give the boys a chance to do laundry in the comforts of a nicely heated hotel and give them another hot meal and a warm bed.
They would be fully rested and fresh before the next show, scheduled for the following day in Moorhead, Minnesota.
Backstage at the Surf, Carroll Anderson contacted Dwyer Flying Services of Mason City to make the flight arrangements. The word began to spread that Holly had chartered a plane for his band and it wasn’t long before some of the other artists heard about the plane and wanted in on the action. One of them, the Big Bopper, was feeling ill with flu-like symptoms and wanted a seat on the flight so he could have time to see a doctor. The Big Bopper managed to persuade Waylon Jennings to give up his seat on the plane. As part of the trade, the Big Bopper gave Waylon a sleeping bag that he had purchased earlier in the day from a sporting goods store to keep himself warm on the next bus ride.
According to Tommy Allsup, throughout the evening at the Surf, Ritchie Valens was continuously asking him, “Are you gonna let me fly guy?” in hopes of getting the last seat on the plane. Ritchie kept asking and Tommy kept saying no. After the show ended, Waylon made his way backstage at the Surf and found Buddy Holly sitting in a chair, leaning it back against the dressing room wall, all while eating a hot dog.
Waylon shared his plans about trading places with the Big Bopper and Buddy joked to Waylon, “Are you really gonna ride that old bus again?” When Waylon confirmed he was because he had made the trade, Buddy laughed and replied, “Well then, I hope your old bus freezes up.” Waylon chuckled and replied back, “Well then, I hope your old plane crashes.” They both laughed it off and continued packing up for the next show.
A short time later, Buddy and the Big Bopper were outside in the parking lot, loading their things into Carroll Anderson’s station wagon for the short drive to the Mason City Airport. Carroll Anderson was accompanied by his wife and young son at his side. Just as the Anderson family were getting back into the car, Tommy Allsup stepped out of the building and approached the car. As he did, Buddy rolled down the window and asked Tommy to go back inside to double-check everything to make sure that nothing was left behind.
Tommy reentered the building through the backstage door and found Ritchie Valens standing in the opposite doorway across the dressing room, signing autographs for adoring fans. On a final effort, Ritchie asked Tommy yet again, “Are you gonna let me fly, guy?” For reasons that Tommy said he could never explain, he reached deep into his pocket, pulled out a 50-cent piece, and said to Ritchie, “Call it in the air.” Tommy flipped the coin high into the air, Ritchie Valens said “heads” and the coin landed on the dressing room floor, heads up. Ritchie placed his hands on his knees, looked down at the coin, raised his head and exclaimed “That’s the first time I’ve ever won anything like that!”
Tommy Allsup immediately walked outside and explained to Buddy Holly that Ritchie would be taking his seat on the plane. He then handed Buddy his wallet and asked if he could pick up a Wells Fargo telegram that his mother was sending to him, and Buddy agreed to do so. Meanwhile, Ritchie loaded his things into the car and a brief time later, they were all on their way to Mason City Airport.
The singers reached the airport just after midnight, and the night of February 2nd slowly slipped into the morning of February 3rd. Jerry Dwyer, owner of Dwyer’s Flying Services, had driven over to Mason City and met the boys at the airport. Jerry Dwyer was a licensed veteran pilot in his own right but on this night, it would be his employee Roger Peterson, a 21-year-old who would be at the controls.
Jerry Dwyer accepted a payment of $36 from each of the passengers and afterwards, they loaded themselves and their luggage into the plane, Jerry Dwyer closed the door, and the plane taxied its way down to the runway. Around 12:55 a.m., the 1947 Beechcraft Bonanza left the runway and headed for Fargo, North Dakota. What no one knew was they would never make it. Instead, these promising young men had a date with destiny. Just moments after they left the Mason City Airport, those four young boys, filled with talent and aspirations, fell from the sky, and into the history books of rock-n-roll.
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