Buddy Holly may have looked cute, but behind those iconic glasses was a fiery rebel who played by his own rules—until that fire went out forever on one of the most tragic days in the history of Rock and Roll.
1. They Called Him Buddy
Charles Hardin Holley, called “Buddy” from an early age by his family, was born in Lubbock, Texas to cash-strapped Baptist parents in 1936. The Great Depression was in full swing and little Buddy was the family’s fourth child, but the family spoiled the baby nonetheless.
But there wasn’t always a lot to go around.
2. They Made Music Together
Buddy’s father Larry rarely kept down a steady job for long, and the family lived in poverty. But even when financial struggles meant the Holleys had to move to a small place far outside Lubbock, they still had one thing that brought them all together: music.
The entire family sang and played instruments, with the exception of Larry, who said, “Someone needs to listen”. But they soon realized that their baby Buddy was different…
3. They Humored Him
When his older siblings entered talent shows, Buddy desperately wanted to join them, even if he didn’t know how to play yet. Once, to humor him, his older brothers let him join them on stage with a violin—but only after they’d greased the bow so it wouldn’t make a sound.
Buddy Holly’s older brothers humored him at first—but before he’d even entered school, he was already making them jealous.
4. He Had The Juice
Holly won his first singing contest when he was just 5 years old. He clearly had the natural talent—but when he was young, he had other things on his mind. He loved the outdoors and spent his days hiking, fishing, and horseback riding.
But there was something else he adored even more: his older brother, Larry. Unfortunately, his brother wasn’t always the best role model…
5. He Idolized His Brother
Buddy wanted to follow his older brother wherever he went, and Larry let him. But Larry brought him places no child should go. Larry was a teenager, and he was far more interested in chasing girls than raising his kid brother.
It led to some awkward moments.
6. He Slept Between Them
Pretty soon, Larry Holley met the girl of his dreams. They quickly married—but Larry still couldn’t shake his little brother Buddy. Larry and his new wife brought Maxine on a camping trip soon after they got married, though I’m sure they quickly regretted it.
Buddy thought he heard a coyote, so he insisted on spending the night sleeping right between them.
7. He Was A Rebel Without A Cause
Buddy Holly grew up getting into trouble with his much older teenage brother. When he became a teenager himself, he took this to the next level. Though he came from a strict Baptist family, Holly chafed against these restraints and started to rebel.
And when Buddy Holly wanted to rebel, he went all the way.
8. He Got Up To No Good
Holly started staying out all hours of the night with his gang of friends. The group whiled away the hours outside of a local cafe making a nuisance of themselves. This one-time good Baptist boy now enjoyed drinking, smoking, cussing, and shoplifting.
But there was one new vice that Holly liked more than any of the others: girls.
9. He Wanted To Get With A Girl
There was a scandalous rite of passage for young men in Holly’s rebellious, teenage crew. One night, Holly mentioned to his friends that he wondered what it was like to be with a woman. That was when his friends decided he should become a man. The boys knew of a rebellious girl who was just the woman for the job.
If it sounds scandalous, just you wait…
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10. His First Time Was Scandalous
Buddy Holly lost his virginity that night—but, well, let’s just say it was more of an ensemble performance than a duet. At least the first-timer Holly had his friends there to show him the ropes!
11. He Found A Good Girl
One Holly popped his cherry, he went full-Pringles and just couldn’t stop. He jumped from one girl to the next—that is, until he met Echo Elaine MacGuire.
Echo was the polar opposite of the girls Holly had been running with. She was pretty, pious, respectable, and came from a well-off, middle-class family. Soon, she and Holly were going steady—but she didn’t realize he was keeping a disturbing secret.
12. He Played Around Behind Her Back
Echo MacGuire was a good, Christian girl, and that meant no doing the dirty before marriage. The teenaged Holly was about as randy as a boy could get, but he respected his girlfriend’s wishes. What he didn’t tell her, however, was that after he dropped her off at home, he went to his old hangouts to find easy girls who would do what she wouldn’t.
But it gets worse.
13. He May Have Had A Love Child
While Holly was dating MacGuire, he also had a side piece who went to the same school as them. Though it has never been confirmed for sure, some sources believe that Holly actually got this mystery girl pregnant.
Allegedly, her family left town in disgrace, and Holly never saw her again, nor did he meet his child.
14. He Picked Up A Guitar
Buddy Holly’s high school years were wild—but it was about to get a lot crazier. He picked up the guitar after his brother brought one back from WWII. He quickly realized that he was good at it, and it provided a distraction from the girls and the partying.
Then one day, he saw something that changed his life forever. Buddy Holly went to see the King.
15. Elvis Changed His Life
This was 1955, and music was about to change because of one man: Elvis Presley. When the King of Rock and Roll performed in Lubbock, Holly was there to witness the spectacle. The show helped him make a decision he’d been mulling over: He was going to make a career in music.
And he got off to a running start.
16. He Played With The King
Holly mostly played country music before, but after seeing Presley, he started to move towards rock and roll. He brought two of his friends into his band, and soon the three-piece was opening for the King across Texas. By January 1956, they were recording with Decca Records as “Buddy Holly and the Two Tones” (the label misspelled "Holley" and the typo stuck).
Everything was going his way—but he was in for some bad news.
17. The Label Screwed Him
Holly hated his first recordings because Decca wouldn’t give him creative control. Even worse, the records didn’t exactly set the world on fire and Decca refused to renew his contract. That was bad enough, but that still wasn’t the worst part: They also told him he couldn’t record his songs for anyone else for the next five years.
But that wasn’t going to stop him.
18. He Made His First Hit Single
Decca tried to handcuff him, but Holly proved slippery. He teamed up with successful music producer Norman Petty and recorded a new track, “That’ll Be The Day”. Buddy enjoyed the creative control he craved, but I doubt even he realized how much he knocked it out of the park.
19. He Became A Star
“That’ll Be The Day” shot to the top of the charts and made Buddy Holly a household name almost overnight. He appeared on Dick Clark’s American Bandstand, then released a follow-up single, “Peggy Sue,” to similar acclaim.
Holly was on top of the world, but not everything was going his way.
20. His Old Life Was Gone
Buddy Holly and his bandmates returned to Lubbock as rock stars—but life had carried on without them. Upon his return, Holly learned that his girlfriend, Echo MacGuire, had dumped him for a new boy at college.
The rejection must have stung—but it paved the way for Holly to find true love.
21. He Fell In Love At First Sight
One day, Buddy Holly took a meeting at Peer-Southern Records, but as soon as he stepped into the office, something—or someone—caught his eye. Maria Elena Santiago was the office’s receptionist, and for Holly, it was love at first sight.
22. He Worked Fast
Holly asked Santiago out on a date before he left the office that day. If you think that’s working fast, you haven’t seen anything yet. He ended up proposing marriage on their very first date! Apparently, his youthful rockstar charm worked, because Santiago said yes and they were married within two months of meeting.
It seemed like a fairy tale love story. Sadly, neither of them realized, this was actually a tragedy. Their days were numbered from the very beginning.
23. His Manager Was Furious
If you think Holly proposing marriage on a first date is shocking, how do you think his manager felt? Norman Petty, the producer who worked on “That’ll Be The Day,” had taken over managerial duties for Holly. He was furious with his new client—for a truly ridiculous reason.
24. He Thought It Was Bad For Holly's Image
Buddy Holly had found his true love, but Norman Petty was far more concerned with Holly’s fans. He was a teen heartthrob, and Petty wanted his adoring fans to think they had a chance with him. How were they supposed to do that if he was married!
This led to a bizarre arrangement.
25. She Was Their "Secretery"
Buddy and Maria Holly went everywhere together. They were a staple of the New York music scene at the time, and when Buddy went out touring, Maria always went with him. However, at Petty’s insistence, she pretended to be the band’s secretary.
Well, maybe pretended isn’t the right word…
26. She Didn't Mess Around
When she went on tour with Holly, Maria actually ended up doing the band’s laundry, helping with equipment set-up, and collecting money at the concerts. Maybe that’s when she started to notice something fishy was going on.
27. She Didn't Trust Their Manager
Maria Elena Holly was no mere trophy wife; she had a good head on her shoulders. She obviously hated being told that Holly had to keep their relationship a secret so his fans could think they had a shot with him. But that wasn’t her only issue with Petty.
When she took a look at Petty’s bookkeeping, she realized that something was seriously wrong.
28. Things Got Messy
The band was already growing frustrated with Petty, but when Maria showed them that he was stealing their royalties, it was time to find someone new. If only it was that simple. Holly tried to find a new manager…who promptly sued him over payment.
This new legal mess meant Holly couldn’t get the money that Petty owed him. He started running out of funds, so he booked a new tour to get his head back above water.
29. Their Tour Was A Fiasco From The Start
Buddy Holly began his Winter Dance Party tour on January 23, 1959. In their rush to hit the road, the band didn’t plan the tour properly. They very quickly realized that this was going to be a nightmare—even if no one predicted how tragic it would become.
30. They Didn't Plan For Winter
The band scheduled as many performances as they could, without any regard for how they would get from one to the other…in the dead of winter. Their unheated tour bus was miserable enough as it is—but things very quickly went from bad to worse.
31. Their Drummer Froze His Toes Off
Within the first few days of the tour, Holly’s tour buses broke down on the freezing cold roads. Twice. Soon, there were gruesome consequences. The band’s drummer got frostbite on his toes so bad that he had to be hospitalized.
But, the tour had to go on, so Holly thought up a solution.
32. He Wanted To Fly
By the time the band made it to Iowa Buddy Holly was done with the frigid tour bus. The prospect of driving through the frigid prairies up to Minnesota was a bridge too far. Instead, he chartered a small plane—a four-seater Beechcraft Bonanza—to take the band North.
33. He Invited His Band
Holly was going to fly, but the rest of the tour still had to take the bus. He was meant to take his fellow band members Waylon Jennings and Tommy Allsup with him, but fate had other ideas.
34. Ritchie Valens
Won Lost A Coin Flip
Holly wasn’t the only one who was fed up with long nights on frozen highways. Another performer on the tour, Ritchie Valens, flipped a coin with Allsup for a seat on the plane. Valens won the flip, and said, “That’s the first time I’ve ever won anything in my life.”
35. Waylon Jennings Made The Right Decision
Allsup lost his seat on the plane in a coin flip, but Waylon Jennings—who later went on to become a pioneering voice in Outlaw Country—gave it up out of the goodness of his heart. The Big Bopper, yet another performer, was sick, so Jennings gave him his seat.
That small act of kindness ended up saving Jennings’ life.
36. The Day The Music Died
The plane carrying Buddy Holly, Ritchie Valens, and the Big Bopper barely made it five miles before it went down in an Iowa cornfield. All three men and their pilot, Roger Peterson, lost their lives. “The Day The Music Died” went down in infamy, but now, the public needed to know: What happened?
37. Holly Was Armed
Just ask anyone who grew up with him: Buddy Holly was not the crystal-clean teen heartthrob he appeared. Case in point: He carried a gun with him. So, naturally, he brought his piece with him in that Beechcraft Bonanza—and it led to some chilling rumors.
38. They Found The Gun
Two months after the crash, a local farmer found Holly’s piece. Public interest in the crash was still at a fever pitch, and it wasn’t long before the discovery reached the papers. But that wasn’t the only thing odd about the crash…
39. The Pilot Wasn't With Them
Another detail picked up on was that Roger Peterson’s body was found 40 feet away from the crash, while everyone else’s stayed much closer. Between the gun and the strange location of Peterson’s body, newspapers began asking the question: Was there foul play involved?
40. His Son Sought The Truth
Conspiracy-minded fans had heard all they needed to hear: Someone had shot the pilot and brought that plane down. It was a chilling capper to “The Day The Music Died”—but it was all a fiction. It took decades, but Richardson’s son eventually commissioned an official autopsy, which proved there had been no foul play. However, that didn’t mean there was no one to blame.
41. They Shouldn't Have Been Flying
The weather was bad that night, but Roger Peterson took off anyway, despite the fact that he wasn’t certified to fly by instruments only. And that wasn’t even the only thing working against them.
42. It Could Have Been The Instruments
The plane had an updated gyroscope that likely worked differently than what Peterson would have been used to. The way this new model worked, Peterson might have thought they were climbing when they were really descending straight into that Iowan cornfield.
But in the end, the explanation might be even simpler: It was Holly's own fault.
43. He Was Too Reckless
Buddy Holly had been reckless ever since he was a boy. His friends frequently mentioned that he thought he was “invincible”. He was, after all, the one who chartered the small plane. He also, at the very least, raised no objections to taking off in inclement weather.
Holly’s wife seemed to think that his recklessness played a factor—and that was something his wife blamed herself for for the rest of her life.
44. Their Love Didn't Even last A Year
Maria Elena Holly met Buddy in June, married him in August…and became his widow before the year was out. But the story just keeps getting worse. She was actually pregnant with his child at the time. Then she heard the news in the worst way possible.
45. He Changed The News Forever
Today, news agencies generally have a strong policy against announcing the identity of victims until the family is notified—and it was Buddy Holly who we have to thank. Holly’s mother heard about her son’s crash on television, at the same time as everyone else.
She screamed and collapsed—but Maria’s reaction was even more tragic.
46. She Couldn't Bear The Grief
Maria Holly found out about her husband’s death on television. In the shock of the moment, she suffered a miscarriage. Her grief was so unbearable, she couldn’t even attend Holly’s funeral, nor did she ever visit his gravesite.
Years later, she gave an interview that explained why.
47. She Blamed Herself
Maria Holly was Buddy’s better half. They spent nearly every moment together, and Maria helped manage his career. However, the pregnant Maria hadn’t felt well enough to join him on the Winter Dance Party tour.
“It was the only time I wasn't with him. And I blame myself because I know that, if only I had gone along, Buddy never would have gotten into that airplane."
48. His Glasses Went Missing
Despite the churning of the rumor mill, authorities eventually deemed the plane crash was simply an unfortunate and tragic accident. But one piece of the puzzle was still missing: What had happened to Holly’s iconic glasses?
Well, they were in for a saga of their own.
49. They Appeared In A Box
Buddy Holly’s glasses would have been one of the most sought-after pieces of Rock memorabilia—if anyone could find them. They remained missing for over 20 years—until a local sheriff found them in a box in the local courthouse.
It turned out, a local found them after the snow melted and handed them to the local sheriff’s office…who simply shoved them in a box and forgot about them. But the story of the glasses doesn’t even end there.
50. His Wife And Parents Fought Over Them
As if Holly’s death didn’t hurt enough, his wife and family had to dig up those old wounds 20 years later—all over a pair of glasses. The glasses belonged to Maria, but Holly’s parents fought her in court over them for an entire year.
Finally, the glasses were returned to Maria. Today, you can see them on display at the Buddy Holly Center in his hometown of Lubbock, Texas.