Once Upon a Time In Iowa: A Tale of Buddy Holly

Once Upon a Time In Iowa: A Tale of Buddy Holly




When I was growing up, I came to personally enjoy the music of Buddy Holly for a period possibly of time more so than any other musician. His music supplied the same level of enjoyment I had received at six years old through ritualistic viewings of Alfred Hitchcock films, as well as his televised series “Alfred Hitchcock Presents”. The premature death of Buddy Holly came as a shock when my father told me about the plane crash which killed the famed musician, along with Richie Valens and “The Big Bopper”, when I was eight years old. At first, I didn’t believe my father, as the grim reality of death hadn’t entirely set in. However, as I got older and more involved with selling music, before the eventual opening of my very own online record store, I often wondered how different the music world would have been had Buddy Holly never gotten on the plane which claimed his life in first place... 


“Once Upon a Time in Iowa: The Unverified True Story of Buddy Holly”




Part One: The Flip of a Coin 


It was a snowy, cold, miserable night. The performance at Surf Ballroom in Iowa had drawn to an end shortly after midnight. The taxi had arrived at Dwyer Flying Service in Mason City, Iowa, shortly after one in the morning. Rather than take the bus to the next venue, as he was scheduled to do after offering his seat to J.P. “The Big Bopper” Richardson, Waylon Jennings, who had been feeling a little pissy, had tagged along with the others.  

After exiting the taxi, which waited nearby toward the end of the tarmac, Tommy Allsup glanced at Richie Valens, who shivered as he held his hands within his pants pockets, teeth chattering away like a jackhammer. The engine of the small Beechcraft Bonanza airplane roared behind them and pilot, Roger Peterson, glanced their way. 

“We gotta get this show on the road,” said Roger. “What’s the damn hold up?” 

“Hold your horses,” said Tommy. “Me and Richie got a little wager. What’s it gonna be, Richie, heads or tails?” 

“Heads,” said a shivering Richie. 

Tommy removed a quarter from his coat pocket which he then flipped into the air. As the coin landed, Tommy removed his hand from overtop, exposing that it had landed on heads.  

“It’s heads, lucky bastard,” said Tommy. Richie smiled.  

“That’s the first time I won anything in my life!” exclaimed Richie. 

Waylon, who had since begun to pace around in an irritated manner, gave Richie an icy stare.  

“Good,” said Waylon sternly. “Now get the hell on the plane.” 

Buddy Holly, who had been feeling ill the past few days, stared at a heated Waylon. 

“What’s been going on, Waylon?” asked Buddy. 

“I’ve been freezing my ass off, is what’s been going on!" said Waylon. “Now, Buddy, I do realize you did line up the plane to make it easier on the rest of us, which I do appreciate, don’t get me wrong. But the kid and J.P. don’t have anything to do with the band. They should take the bus like everyone else.” 

J.P., gave Waylon a defensive look. 

“I’m struggling to figure out why you’re here, seeing that you already forfeited me your seat on account of me being sick as a dog,” said J.P. “We’re all friends here, Waylon.” 

“Friends? We hardly know each other!” exclaimed Waylon. “When it comes to the words of a two-bit musician, there ain’t nothing you have to say that I want to hear.” 

“Two-bit musician is rich coming from the hired hand,” said J.P., followed by a slightly arrogant laugh, which was proceeded by a fit of coughing.  

Waylon, who was fuming in rage, turned to a flabbergasted Buddy. “Buddy, I love you like a brother, you know I do. But I hope your ol’ plane crashes.” 

Waylon turned in the opposite direction and began walking off toward the parked taxi. Buddy, who had been sensing a strain building between himself and his good friend, turned to Roger.  

“You fellows can go ahead,” said Buddy, who had then started to follow after Waylon. Tommy stared toward Buddy in shock. 

“But you booked the flight,” shouted Tommy. “What about your seat?” 

“You can have it,” yelled Buddy, who then quickened his steps in the direction of Waylon. Roger then glanced at the three men who stood before him. J.P Richardson, Richie Valens and Tommy Allsup.  

“You heard him, boys,” said Roger, who then proceeded to board the plane, followed by J.P. 

“Looks like that coin toss was a blessing for the both of us,” said Tommy, as he followed behind a frozen, yet relieved Richie aboard the plane, which took off down the runway and into the air a moment later. 

Waylon entered the taxi. Buddy followed close behind. 

“Hey Waylon, hold up,” said Buddy. 

Waylon held the door open, feeling slightly frustrated as Buddy took a seat beside him, closing the door behind himself. The taxi driver placed his foot on the gas and started driving back toward Clear Lake, Iowa. 

“You missed your ticket out of here,” said Waylon. 

“We’ll make it to the next venue... somehow,” said Buddy. “And those boys will be just fine. It’s you I’m worried about.” 

“You’re worried about me now?” said Waylon, followed by a sarcastic laugh. “What has you so concerned?” 

“You don’t seem as cheerful as you once were,” said Buddy. “I know the road can get to be stressful. I just hate to see a friend in such a state of misery over something that should bring out the best in him. That goes for all you guys. I feel horrible about what happened to Carl.” 

“You act like he got a foot amputated, or something worse,” said Waylon. “If he wore a proper pair of shoes in the first damn place, he never would have found himself in the hospital.” 

“He could have lost his toes, Waylon,” said Buddy. “And if he had, I would have tortured myself knowing that I had a role to play. That was the reason I lined up the plane, for the benefit of all of us. Things don’t always go as planned. That’s to be expected. But if something is bothering you, and you’re bringing that on the road with you, it’s going to affect all of us. Do you see what I’m getting at?” 

Waylon hesitated. Something had been bothering him, which he had yet to bring up to Buddy. 

“You’re right,” said Waylon. “I’ve been an asshole, and I’m sorry. It’s not the road that’s been bothering me. It’s the music.” 

Buddy was at a loss. 

“The music?” asked Buddy. 

“It’s not my own,” said Waylon, who felt a pinch in his throat. “I’ve enjoyed the opportunity to play with you. I honestly have. But rock and roll, it ain’t my style. And being a bass player for the great Buddy Holly – I want more for myself.” 

Buddy stared off to his front as the bright lights of Clear Lake came into view. He then turned toward Waylon with a half-smile.  

“Let’s go get a coffee,” said Buddy.  

“It’s past one in the morning, Buddy,” said Waylon. “We’ll be shit out of luck finding a diner open at this time.” 

“On the drive over to Mason City, I noticed a place that still had its lights on,” said Buddy. “It could be worth a try seeing whether or not they’re still open.”  

“I highly doubt they are, but what the hell, you only live once,” said Waylon, as the taxi chugged ahead. 

Roughly half an hour later, the taxi had arrived outside “Millie’s Diner”, a twenty-four-hour diner (years ahead of their time) which was located a few blocks from the bus stop. Buddy paid the taxi driver before the two friends were briefly back in the cold and soon into the warmth of the bright lit diner.  

The diner itself was as dead as a mortuary. Not a soul in sight until a curvy waitress with curled blonde hair, bright red lipstick and a pink dress approached from the back kitchen. Waylon felt his heart beat faster as she approached, before he switched on the charm. 

“No one told me all the pretty girls hide out in a little town like Clear Lake, Iowa,” said Waylon, with a smile. The waitress blushed.  

“You boys must not be from around here,” said the waitress.  

“You got that right,” said Waylon. “But something tells me it won’t be the last we head out this way.” 

The waitress and Waylon gave each other a flirtatious look, before the waitress turned to Buddy, who she soon gave a knowing expression.  

“Hold on just a second,” said the waitress. “You’re Buddy Holly. I can’t believe it! There was something familiar about those thick framed glasses.” 

Buddy smiled, feeling shy. Waylon felt slightly jealous with the attention of the beautiful waitress now solely on Buddy. 

“Yes,” said Buddy. “I’m Buddy Holly, and this is my good friend, Waylon Jennings. He plays bass in my band from time to time. He’s a very talented musician.”  

“Since I now know both of your names, mine is Betty Lancaster,” said Betty, the waitress. “Would you prefer a table or booth?” 

“Table,” said Waylon. “And preferably one away from the window. It would be nice not to be reminded of the cold for a few minutes.” 

“You got it, Waylon,” said Betty with a smile. The friends then followed Betty toward a table located toward the center of the diner. As they made their way over, Waylon checked out Betty’s ass. Buddy, who was happily married, thought of his wife Maria, and how he longed to be out of the cold with her in his arms. The friends took a seat across from one another, as Betty glanced down at them. 

“Can I start you guys off with a coffee?” asked Betty. 

“That would be very kind of you,” said Buddy. “How are the cheeseburgers? I haven’t eaten in a few hours. Are you hungry, Waylon?” 

“Only if you’re paying,” said Waylon. Both men, as well as Betty, all shared a laugh. 

“I betcha that every diner in Iowa claims to have the best cheeseburgers,” said Betty. “But when I tell you that Millie’s has the best cheeseburgers in all of Iowa, then I mean that Millie’s has the best goddamn cheeseburgers in all of Iowa.” 

“Well in that case, we’ll get two cheeseburgers and fries,” said Buddy. “Along with the coffees.” 

“You got it,” said Betty. As Betty walked toward the kitchen, Waylon once again found himself checking out her sexy body.  

“I’ll tell you Buddy, I’d love to skip the meal and go straight for dessert, if you catch my drift,” said Waylon, with a smile. “How do you help yourself, knowing that you could have any piece of tail that you set your sights on?” 

“Why settle for a cheeseburger, when I have a steak at home?” asked Buddy. Both men shared a laugh. “So what’s been on your mind?”  

“Can’t we just skip the serious talk for a few minutes,” asked Waylon. “I really am starving.” 

“You and me both,” said Buddy. “If she brings out the cheeseburgers in the next five minutes, you can eat mine as well.” 

“I already cost you your seat aboard the plane,” said Waylon. “And you’d be prepared to give me your burger?” 

“I would if I didn’t want food poisoning, which is what you’d get with a burger on the stove for only five minutes,” said Buddy. “You know, going back ten years as I was growing up in Lubbock, I had envisioned all of this. The fame, the success, all of it. None of it has come as a surprise. I’m not arrogant either. You know this. But sometimes, and I believe this wholeheartedly, if you are on the right track, then it can feel like walking on water. That how you feel?” 

Waylon hesitated. 

“Not lately,” said Waylon. “I mean, to have the opportunity to play with you and the boys during this winter tour, or whatever the hell you call it, it’s been the opportunity of a lifetime. You’ve been one hell of a mentor to me. Maybe this is my pride talking, but playing in a rock and roll band, rather than playing for myself, has made me feel like a fly on the wall... country is where my heart is. I hope you don’t take what I’m saying as a sign of me being ungrateful, because that’s not my intention. It’s just --” 

“You don’t need to explain yourself any further,” said Buddy. “I understand. Your heart isn’t in it. You should never feel inclined to do anything you don’t want to.” 

Betty suddenly appeared with a tray in hand which held two coffees and some creamer. She placed the coffees to the front of the friends, while giving them each a smile.  

“The food is going to take fifteen minutes or so longer,” said Betty. “I hope you fellows don’t mind the wait?” 

“No, not at all,” said Waylon. “What time do you get off?” 

“My shift ends at four,” said Betty. “Why do you ask?” 

"I’m feeling a little down in the gutters,” said Waylon. “You feel like getting a drink with a southern gentleman like me?” 

“I would, but I have to get home to my son when we close up,” said Betty. 

“I could come over and teach the little fellow to play guitar in the morning,” said Waylon. 

“I don’t think my husband would appreciate that,” said Betty. “I hope you gentlemen enjoy the coffee. If you need anything else, just give me a shout.”  

Betty walked off toward the kitchen. Waylon felt discouraged after hearing the news of Betty having a husband, which he highly doubted. 

“You honestly believe that?” said Waylon. “A woman as fine as her being forced to work a job like this as her good for nothing husband lounges around at home. I doubt she has a husband. When I’m on top of the music world, there won’t be a waitress alive that’ll reject my advances.” 

“What’s this mean for us?” asked Buddy. 

“I think we both know what this means,” said Waylon. “You’re on a collision course with your own destiny, and so am I. Maybe it was meant to happen like this. That doesn’t mean that we have to end our friendship. I think that would be foolish.” 

“Yeah, so do I,” said Buddy. “I hope those fellows arrive safely.” 

“They'll be just fine,” said Waylon. “You worry too much, Buddy. All work and no play is never good for anybody.” 

“I know,” said Buddy, as he readjusted his glasses. “Have you written any songs?” 

“Yeah,” said Waylon. “I’ve written a few, but not to the extent that you have. You’re a song writing machine. My heart would be in performing.”  

Waylon grabbed the creamer, poured some in his coffee, before putting in a bit of sugar. He then took a sip, let out a breath of air, before staring at Buddy who carefully did the same with his own. 

“Wouldn’t it be ironic as hell if that plane did crash, after I uttered those words?” asked Waylon. 

“Let's not think that way,” said Buddy. “Sometimes its best just to shut up and enjoy the coffee.” 

The friends did just that. They enjoyed their coffee, followed by their burgers, before they took a taxi to a nearby motel, knowing that come the morning, they would both be heading their separate ways. Waylon had preferred sleeping in his own room, rather than sharing one with any band members while on the road. This related mostly with the prospect of potentially finding a piece of tail to bring back to his room for a night of passion, which he did on occasion. For whatever reason, both men struggled to sleep that night. Maybe it was the realization that they wouldn’t be performing together again, or perhaps the anticipation of the future which caused them both to have a restless sleep. At any rate, they awoke the next morning, and after cleaning up their individual motel rooms, had headed to the front desk to hand back the keys to their rooms.  

Waylon had entered the lobby first, followed by Buddy. As they gave each other a look, they turned to a fat, balding man who worked the front till. 

“Morning,” said the fat, balding man. “You fellows have a good sleep?” 

“Yeah,” said Buddy.  

Suddenly, both Buddy and Waylon overheard the broadcast which came from the radio behind the counter. 

“Reporting from Clear Lake, Iowa,” said the radio announcer. “Three of the nation's top three leading rock and roll singers, Richie Valens, Buddy Holly and J.P. “The Big Bopper” Richardson, died last night with their pilot in the crash of a chartered plane, following an appearance before 1000 fans at Clear Lake last night. They chartered a plane last night in Mason City which took off at roughly 1:30am for Fargo, North Dakota...” 

Buddy felt a sinking in the pit of his gut, as he locked eyes with Waylon. A solitary decision not to board the plane had saved his life, but in his place, Tommy Allsup had perished, along with fellow musicians Richie and J.P. who he had considered to be his friends. At this point, the fat, balding man behind the counter glanced down at the registry and noticed the signature left by Buddy. 

“Aren’t you Buddy Holly?” asked the fat, balding man.  

“Yeah,” said Buddy, who was now on the verge of tears. “I’m Buddy Holly. And those were my friends, and this is all my fault.” 

“Buddy, this ain’t your fault. No one could have predicted this,” said Waylon, who then attempted to place a calming hand on his friend's shoulder, which Buddy quickly pushed away.  

“I should have been on that plane!” yelled Buddy. “If you weren’t being such a self-righteous asshole, Tommy would have still been alive!” 

“Hold up just a second,” said Waylon. “You’re mad at me because you didn’t get on the plane which would have killed you? The way I see things, I saved your goddamn life!” 

Waylon abruptly handed the key to the fat, balding man behind the counter before giving Buddy a judgmental stare.  

“I saved your life, you ungrateful piece-of-shit!” shouted Waylon, before stepping outside into the brisk cold of the morning. Buddy, who felt tears stream down his cheeks, proceeded to cry as memories of his perished friends flashed before his mind. The realization that him deciding to line up a plane, would haunt him for years.  

Buddy Holly would reunite and continue to perform with The Crickets until they disbanded in early 1965. His bandmates had noticed a change within him, and not a change for the better, which lead Buddy to write music which was missing its initial appeal. Rather than writing songs about love, his music had become consumed by themes of tragedy, likely brought on by the guilt Buddy felt regarding the deaths of his friends, which often clouded his mind to the point of disarray. 1965 had also been the year his beloved wife, Maria, had filed for divorce. This crushed the singer. With his wife and bandmates both gone, Buddy had turned to alcohol as a means to cope with the grief.  

Waylon, who had released his debut album, At JD’s, in 1964, had felt awful for the way in which his friendship with Buddy had ended, and also felt partly to blame for the direction Buddy’s life had gone. It was around this time that Waylon learned that John Lennon was a massive fan of Buddy Holly’s music, which led Waylon to contact John Lennon in hopes of setting up a meeting between John and Buddy.  

It was on December 26th, 1965, when Buddy got the call that would change his life for the better... 

End of Part One 

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