whan Jennings may have been a country music legend but he was never one to follow the Nashville rule book a true Outlaw in every sense of the word he carved his own path battling addiction defying the music industry and dodging more than a few brushes with the law his life was a constant fight but through sheer grit rebellion and sheer luck he managed to survive it all from narrowly escaping a doomed plane crash to burning through an astonishing $1,500 a day on drugs Jennings lived on the edge somehow despite pushing the
limits time and time again he managed to beat the odds and tell his story though just barely that Fearless attitude was ingrained in him from the start Jennings embod.i.ed the Brash confidence of a Texan something he acknowledged himself when you’re born in Texas you think that you’re a little bit taller a little bit smarter and a little bit tougher than anybody else born on June 15th 1937 to farm laborers Loren and William Jennings he was raised in the small town of Littlefield Texas his family worked the land scraping by on whatever they could
earn from cotton farming though money was tight his childhood was filled with the independent spirit that would later Define both his music and his Persona that Texas Swagger would serve him well throughout his career but it would also land him in plenty of trouble despite his family struggles Jennings showed early signs of musical Talent when he was just 8 years old his mother scraped together enough money to buy him a secondhand guitar she taught him to play 30 pieces of silver and from that moment on he was hooked his passion
for music grew quickly he began performing at local Gatherings and his natural Talent earned him a spot on a TV talent show which he won by the time he was 14 he had his own weekly 30-minute radio show an incredible feat for someone his age it was clear that music was his calling but while his star was rising in one area of his life another was rapidly falling falling apart Jennings had no love for school and the rigid structure of the classroom never suited his rebellious nature discipline was harsh back then with public paddings
being a common form of punishment one day when the principal came toward him with a paddle Jennings decided he had had enough in a bold Act of defiance he grabbed the paddle right out of the stunned man’s hands true to form he didn’t stop there staring caring down the principal Jennings declared that he was going to do the paddling instead his confidence must have been convincing because what followed was an intense 2-hour standoff the situation only ended when the School’s football coach intervened shortly after that the
superintendent likely fed up with jennings’s Antics pulled him aside and suggested that he’ leave school for good at just 16 years old Jennings walked away from for Al education forever setting himself on the road to becoming one of country music’s most rebellious and legendary figures whan jennings’s father didn’t try to stop him from dropping out of school instead he offered some tough love telling him if you’re smart enough to quit school you’re smart enough to work and work he did and what would be one of the first
times Jennings unknowingly dodged disaster he credited his father’s insistence on hard labor with keeping him out of trouble while other dropouts in Littlefield were finding trouble Jennings was too exhausted from long hours doing grueling dead-end jobs The Experience only strengthened his determination he knew he needed a way out of Littlefield and he was going to find it Jennings realized that his Escape Route was right in his hands his guitar he didn’t need formal lessons or music theory to know that playing was
his way forward ironically despite his Raw Talent he had once been expelled from music class for lack of musical ability but he didn’t let that stop him he poured everything he had into his music playing as if his life depended on it because in many ways it did his Relentless passion soon began paying off opening doors that a kid from a small Texas town could have only dreamed of his Talent didn’t go unnoticed Jennings secured regular gigs at a local country radio station where his deep commanding voice caught the attention of listeners
he also landed a job as a DJ in lck Texas spinning records and soaking in the music scene it wasn’t just his career that was taking off his personal life was too at just 18 years old he married his first wife Maxine Carol Lawrence for the first time Jennings felt like he was moving forward finally Breaking Free from the small town life he had wanted so desperately to leave behind but just when he thought things couldn’t get any better fate had an even bigger surprise in store working in music meant Jennings was constantly
surrounded by artists but one encounter changed his life forever among the many musicians he met one saw something special in him none other than Buddy Holly the rising rock and roll star from lck Holly was immediately drawn to jennings’s Unique voice and raw authenticity he told him the way you sing there’s no limit and decided to take the young Texan under his wing but there was just one problem Jennings wasn’t exactly star material just yet at the time Jennings didn’t have the polished look of a performer destined
for the spotlight His Radio colleagues were embarrassed by his Shaggy haircut rumpled clothes and the fact that he seemed to wear the same shirt all week Holly saw pass the rough edges and took it upon himself to refine jennings’s image giving him a much needed style upgrade by the time Holly was finished Jennings was nearly unrecognizable with his new look and growing confidence he was ready to step into the world of professional music but just as everything seemed to be falling into place tragedy loomed on the horizon
one that would change jennings’s life forever recognizing jennings’s Raw Talent Holly took him under his wing booking him a recording session and offering him a spot on his upcoming Winter Dance Party tour but there was one problem Jennings had never played bass that didn’t stop Holly as Jennings later recalled I couldn’t have been more surprised when buddy walked into the station one day pitched me an electric bass guitar and said you have two weeks to learn to play that thing with no formal training Jennings had to teach
himself on the fly but he wasn’t about to let this chance slip away despite his inexperience Holly saw something in Jennings that others didn’t Jennings himself admitted he was green as a gourd when it came to playing in a professional band but Holly was confident he’d catch up soon Jennings was part of Holly’s touring lineup joining other rising stars on the Winter Dance Party circuit it seemed like a dream come true but reality hit hard once the tour began the road was far from glamorous and Jennings quickly
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realized that life on tour was more grueling than he had imagined the Winter Dance Party tour was relentless with 25 shows scheduled back to back leaving no time for rest the musicians traveled across the Frozen Midwest in in an unheated bus driving for hours through treacherous winter conditions on poorly maintained rural roads the brutal cold was unbearable and when the bus inevitably broke down Jennings and his fellow performers were left stranded in subzero temperatures many of them including the Big Bopper developed
severe cases of the flu and some even suffered frostbite with exhaustion setting in and the conditions worsening some something had to give frustrated with the miserable travel situation Holly decided to take matters into his own hands in an era long before private jets and luxury tour buses he made a bold decision he chartered a small plane for himself his guitarist and Jennings the plan was simple avoid another brutal overnight bus ride arrive at the next venue well rested and finally get some relief from the Relentless cold
but fate had other plans as words spread about the chartered flight other musicians began asking for a seat the Big Bopper who was suffering badly from the flu approached Jennings and pleaded for his spot Jennings sympathetic to his condition agreed to give up his seat telling him if it’s okay with buddy it’s okay with me meanwhile across the room another of Holly’s band members Tommy alsup lost a COR toss to Richie valins securing vein the last available seat on the plane no one could have known that this simple exchange would change music
history forever in the early hours of February 3rd 1959 the small plane carrying Buddy Holly Richie vains and the Big Bopper crashed into a frozen field in Iowa killing everyone on board it was a tragedy that would later be remembered as the day the music d.i.ed Jennings who had unknowingly escaped d.e.a.t.h that night would carry the weight of that moment for the rest of his life the next morning as the Winter Dance Party tour bus arrived in Morehead Minnesota the surviving musicians were exhausted and Frozen from another brutal ride while
they tried to warm up the tour manager stepped into the hotel to check in but moments later he came rushing back out his face said it all something was very wrong Jennings barely had time to react before Holly’s guitarist went inside to get more information when he returned he delivered the news that would change jennings’s life forever Buddy Holly Richie veilance and the Big Bopper had d.i.ed in a plane crash the weight of the tragedy was crushing losing his friend and Mentor along with his fellow tour mates Jennings couldn’t imagine picking
up his guitar again but the agency managing the tour gave the remaining musicians a harsh ultimatum either finish the tour or go unpaid forced to push through his grief Jennings went back on stage but the music felt Hollow once the tour ended he returned to his old DJ job at the radio station in Leck but he was a different man the high energy Wildman personality that had made him a standout was gone I was empty drained of hope he later admitted and as if that wasn’t enough his personal life was beginning to fall
apart too Jennings wasn’t just grieving he was haunted the crash that took Buddy Holly’s life wasn’t just a tragedy for him it felt like a cruel twist of fate he hadn’t just given up his seat to the Big Bopper his last conversation with Holly had ended in a joke that would torment him for years the night before the Crash Holly had teased Jennings about staying behind on the freezing tour bus instead of flying I hope your damn bus freezes up again holia joked in response Jennings shot back with a playful but fateful remark well I hope
your plane crashes when news of the accident broke Jennings a deeply superstitious Southern boy was overwhelmed with guilt though logically he knew his words had nothing to do with the tragedy he couldn’t shake the feeling that he had somehow cursed his friend it was a burden that weighed heavily on him for the rest of his life while Jennings was spiraling internally his home life wasn’t any better one night he came home late to a shocking sight his wife Maxine standing on a chair with a necktie around her neck
tied to a light bulb fixture the moment he walked in she jumped the bulb shattered and she crashed to the floor Jenning surprisingly unfazed dismissed it as one of Maxine’s Twisted jokes but the truth was their marriage was unraveling despite knowing they weren’t meant to be together they continued having children in 1960 their third child was born in a heartbreaking tribute to the friend he had lost Jennings named his son buddy as Jennings tried to support his growing family life only became more difficult when Maxine’s
father fell seriously ill they packed up and moved to Arizona to be closer to him Jennings bounced between radio stations trying to make ends meet but nothing seemed to last he was lost drifting without Direction until he finally found the courage to return to the one thing that had always saved him music stepping back on stage he took the first step toward rebuilding his life setting the stage for the legendary Outlaw country career that lay ahead once again music gave whan Jennings an escape this time from his crumbling marriage to Maxine
life on the road had always been filled with temptation but one night in a smoky Club he walked straight into trouble of all the honky ton in all the towns he ended up at lind’s a bar owned by a fiery noons older woman who didn’t just hire him to play Play She quickly became something much more their connection was immediate and before long things heated up fast Jennings had been unfaithful before and Maxine likely knew what went on when he was away on tour but this time was different what he thought was just another fleeting Affair turned into
something much more serious Jennings later admitted that Lynn was great in bed and had him by the yin-yang on a downhill Pole he was caught up in the thrill of it all completely unaware that his wife who was now pregnant with their fourth child was about to turn his world upside down somehow Maxine managed to get the phone number to Lyn’s apartment and when Lynn answered the call everything came crashing down despite the chaos in his personal life Jennings refused to let anything slow down his career by the mid 1960s he had divorced
Maxine married Lynn and moved to Nashville ready for a fresh start it was there that he recorded his debut album folk country officially launching the next phase of his musical Journey it was an incredibly productive time for Jennings and he seemed Unstoppable but there was another reason for his high energy lifestyle one that would soon take a dangerous turn shortly after arriving in Nashville Jennings found himself sharing caring a tiny one-bedroom apartment with none other than Johnny Cash Cash already deep into
his own struggles was popping amphetamines like candy and it didn’t take long for Jennings to follow suit he later boasted I prided myself on the fact that I could take more pills stay up longer sing more songs and screw more women than most anybody you ever met the drugs kept him going fueling his long recording session and wild nights unfortunately for Lynn cash wasn’t the only person Jennings was getting close to after 5 years of marriage jennings’s relationship with Lynn was falling apart and it was entirely his fault while
still technically married he had secretly started seeing another woman Barbara a tall blonde who also happened to be the daughter of a millionaire he was so infatuated that he moved her into an apartment just down the hall from where he and Johnny Cash lived when his divorce was finalized he wasted no time making Barbara his new wife her father eager to ensure his daughter’s happiness offered Jennings anything he wanted but there was just one problem what Barbara wanted most was something Jennings couldn’t give whan Jennings was never
built for a quiet settled life Fidelity had never been his strong suit his third wife Barbara tried to keep him in check but Jennings was a force of nature to make matters worse Barbara had the means to fight back in ways most wives couldn’t on one particularly wild night while touring with Hank Williams Jr Jennings had mix so many uppers and downers that he became completely unhinged Loretta Lynn witnessing his state had to physically March him around backstage in an attempt to sober him up but even in a drug fueled Haze Jennings
wasn’t about to pass up a good time that night he took a woman back to his room assuming she was just another fan looking for some after hours fun what he didn’t realize was that he had just walked straight into a trap Barbara wasn’t naive she had a feeling her husband was cheating and she was determined to prove it instead of waiting for him to slip up she hired a private investigator to go undercover that supposed groupy Jennings had Charmed she was actually a detective sent by Barbara to catch him in the ACT
once she had the evidence she needed she didn’t hold back enraged she shredded jennings’s only rhinestone suit and smashed one of his prized guitars against the wall their fights were getting worse by the day Barbara wanted him to slow down settle into a stable home life and give up his Reckless ways but Jennings made it clear that wasn’t an option I wasn’t about to stop playing guitar to keep my home life together he later admitted with no way to reconcile their differences marriage number three came to a fiery end and with that
Jennings fully embraced the chaos in his own words he went wild the next chapter of his life was nothing short of Mayhem fueled by an endless supply of pills Jennings spent his days and nights lost in a whirlwind of Music drugs and women at the height of his excess he was reportedly taking up to 30 amphetamines a day going for days without sleep his appetite for partying was insatiable one particularly notorious night in Louisville Jennings had women stashed in different hotel rooms on three separate floors running purely on
adrenaline and chemicals he spent the night sprinting up and down the emergency staircase bouncing between them like a man on a mission but even Jennings had limits the non-stop drug use sleepless nights and endless cycle of partying were starting to take a toll his once lean frame had dwindled down to just 138 lb 62 kg and he later admitted that he was bent on self-destruction his Reckless lifestyle was catching up with with him just when it seemed like he was heading toward a Breaking Point something or rather
someone intervened in 1969 Jennings met singer Jesse cter and everything changed he later called her the best thing that ever happened to me the two quickly fell in love and got married the same year if anyone thought Jennings would stay single for long they didn’t know him very well for the first time Jennings had a wife who didn’t see his music as a threat she was part of the same world together they became country music’s most dynamic couple recording Duets and even earning a Grammy nomination in 1970 for their rendition of suspicious minds
it seemed like Jennings had finally met his match someone who understood his passion for music and could keep up with his Wild Spirit but while their love was real their struggles were far from over whan Jennings had always been committed to his music but years of hard living were finally catching up to him the Relentless touring the late nights and the drugs had taken a toll on his body eventually he was hospitalized with hepatitis leaving him bedridden with far too much time to think as he lay there he took stock of his life after a decade
of grinding it out on The Honky Tonk circuit he was sick drowning in debt thanks in part to three divorces and alimony payments and now had the IRS breathing down his neck the dream was turning into a nightmare Jennings was on the verge of giving up ready to walk away from it all and go back to dejing but then his drummer came up with an idea that changed everything Jennings left the hospital with a new mission to finally break free from the constraints of Nashville’s music industry his drummer’s advice was simple Embrace
a rock and roll attitude Jennings had always loved country music but he had no patience for the rigid expectations of the Nashville establishment he despised The Rhinestone suits the meddling producers who tried to polish his sound and the record labels that controlled his career while keeping most of the profits if he was going to make music it would be on his own terms if jennings’s life were a movie this would be the moment where we flash back to Buddy Holly’s advice don’t ever let them tell you what to do and never put limits on
yourself don’t back up those words stuck with him with a rebellious Spirit a Cutthroat new manager and the unwavering support of Jesse couter Jennings was finally ready to take control of his Destiny he wasn’t just going to change his own career he was about to change country music forever his manager fought hard to negotiate a better deal securing Jennings more creative freedom and a bigger paycheck than he had ever received before and the gamble paid off in June 1974 he released this time which became his first number one hit suddenly
Jennings wasn’t just another country singer he was a Bonafide Superstar his signature looked dark sunglasses a bushy beard and a wide brimmed black hat became instantly recognizable he had done it his way proving that country music could have an outlaw Edge but with success came new Temptations Just as Jennings was finally Breaking Free from the industry’s grip another dangerous Force took hold of him his drummer Richie Albright had a plan to get him off amphetamines by introducing him to to something stronger
cocaine as comedian Robin Williams once joked cocaine is God’s way of saying you’re making too much money for Jennings that couldn’t have been more true when wanted the Outlaws featuring Jennings Jesse Colter Willie Nelson and Tom Paul Glazer became the first country album to sell over a million copies jennings’s Fame skyrocketed but with that success came an expensive new habit as Jennings later admitted I liked it for the next 10 years I liked it what started as a way to keep up with his grueling schedule quickly spiraled
into something far more destructive whan jennings’s cocaine habit had spiraled out of control draining his bank account at an alarming rate at its peak his addiction was costing him a staggering $1,500 a day every everyone around him knew he had a problem including law enforcement in 1977 during a recording session Jennings received a package from his manager the moment he peaked inside he knew exactly what it was his expected shipment of cocaine but this time there was a serious problem Jennings set the package down and went back to recording
but suddenly he heard something strange in his headphones the sound engineer had accidentally left the TalkBack button pressed allowing Jennings to overhear an unexpected conversation Drug Enforcement Administration daa agents had just arrived and they were saying they had tracked a suspicious package containing Contraband Jennings always quick on his feet knew he had to act fast in a split-second move he made what would become one of the most legendary tosses in country music history discreetly ditching the package right under the
noses of federal agents but he wasn’t out of trouble just yet a true Outlaw never loses his cool and Jennings played it perfectly sitting in the soundproof booth he knew the agents had no idea he could hear them instead of panicking he did the most whaling thing possible he carried on with the recording session playing even louder just to mess with them and in true Outlaw fashion he ended up using that exact take on his album meanwhile the DEA agents convinced they had him cornered were about to make a critical mistake the DEA had been so
confident in their operation that they got careless in their rush to bus Jennings they had made a rookie error the search warrant They Carried had the wrong address legally they could only search jennings’s office but the pack pack AG had been sent to the recording studio instead while the agents stood around helplessly waiting for an updated warrant Jennings seized the opportunity a few moments later they heard the sound of a toilet flushing and just like that their evidence had disappeared literally going down the
drain the drug bus turned into a media circus with Jennings at the center of it all for months the court case dragged on costing him $100,000 in legal fees but in the end the DEA had nothing on him and the charges were dropped Jennings always wanted to turn Misfortune into opportunity took full advantage of the publicity he even wrote a song about the ordeal don’t you think this outlaw bits Dunn got out of hand which became a hit however even escaping the DEA wasn’t enough to slow him down despite the close call Jennings continued his hard
living ways with no intention of giving up the drugs that fueled his lifestyle in 1979 wayin Jennings took his unmistakable Southern draw and DJ background to a whole new level as the narrator of The Dukes of Hazard he once described the show as a moonshine excuse for car chases and watching Catherine box behind and cut off jeans his voice fit the role so perfectly that The Producers asked him to write and perform the theme song the result was good old boys which became not only the show’s signature tune but also the biggest hit
of jennings’s career while his career was thriving his personal life was unraveling Jesse Colter his wife had watched him battle addiction for years but she knew she couldn’t force him to quit his drug use was no longer just a personal Vice it was starting to affect his music he began hearing things that weren’t there his instincts dulled and his once legendary creative spark was fading but it wasn’t until an incident involving their three-year-old son shooter that Jennings finally hit rock bottom by 1984 Jennings had been given
more than one second chance in life having narrowly escaped Buddy Holly’s doomed plane years before but nothing shook him quite like what happened next despite his attempts to keep his drug use hidden little shooter stumbled upon one of his father’s straws and started mimicking him sniffing from it Jennings was horrified in that instant he knew he had to make a change that moment more than any warning from doctors or please from loved ones pushed him to seek help and finally kick his addiction however even after getting clean Jennings wasn’t
one to avoid controversy in 198 5 during the recording of We Are the World he made headlines for all the wrong reasons more than 45 of the world’s biggest musicians had gathered to record a charity single to support famine relief in Africa when Stevie Wonder suggested incorporating Swahili lyrics into the song Jennings reportedly scoffed no good old boy sings in Swahili with that he walked out of the studio though the the final version of the song didn’t include Swahili jennings’s name still appeared in the credits whether or not he ever returned
to finish recording remains a mystery regardless we or the world became a massive success raising over $80 million for humanitarian Aid meanwhile jennings’s career and his health began to decline though he had conquered his drug addiction Jennings replaced one Vice with another he began chain smoking burning through an astonishing seven packs of cigarettes a day his eating habits weren’t much better his meals consisted of three grilled cheese sandwiches for lunch a dozen reff fried donuts for a snack and all the chicken
fried steak biscuits and gravy he could devour while he had been clean for 4 years his new lifestyle was catching up to him fast eventually his body couldn’t take the abuse anymore Jennings narrowly avoided a heart attack but ended up needing quadruple bypass surgery when he woke up from the operation he was shocked to see Johnny Cash by his side but cash wasn’t just visiting he was in bad shape himself doctors took one look at him ran some tests and immediately scheduled him for an emergency bypass surgery of his own during their recovery
the two Country Legends found humor in the situation laughing about how how Fame meant nothing when you were stuck wearing a backless hospital gown but the health scares didn’t stop there years of hard living had taken their toll in addition to heart problems Jennings was diagnosed with Type 2 Diabetes by 2000 the pain in his leg had become unbearable forcing him to stop touring surgery didn’t improve his circulation and in 2001 doctors had no choice but to amputate his his foot the man who had once outrun the law and lived life at
full speed was now facing a battle he couldn’t win despite his declining Health jennings’s Legacy was undeniable in 2001 he was inducted into the Country Music Hall of Fame an honor that recognized his incredible influence on the genre sadly he was too ill to attend the ceremony just a few months later on February 13th 20 2 Jennings passed away in his sleep from complications related to diabetes whan Jennings was a force of nature raw rebellious and undeniably talented he changed country music forever but his wild lifestyle
eventually caught up with him even in his final days he remained true to himself refusing to conform or compromise his legacy lives on in the music and the stories and in The Outlaw spirit that continues to inspire artists today what’s your favorite whan Jennings song let us know in the comments and if you enjoyed this look into his life be sure to like subscribe and check out our next video on another music legend thanks for watching
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