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Waylon Jennings Took This One Terrible Regret to the Grave

Known for his rugged individualism and for helping popularize the grittier, rock-infused genre known as outlaw country. Waylon Jennings always seen as a bit of a wild card in Nashville. He demanded the freedom to be able to record whatever material he pleased while working with his choice of musicians. And to be fair, as one of country’s biggest legends, Waylon earned the right to make such demands!

Jennings first picked up a guitar when he was just 8 eight years old and performed on Wyoming’s KVOW radio station when he was 12. He then formed his first band, The Texas Longhorns.

When he turned 16, Jenning dropped out of high school to jump headlong into pursuing his dream of becoming a musician. For the next several years, he worked as a performer and DJ on several radio stations in Phoenix and Coolidge, Arizona.

It was in 1958 that Waylon began working with a musician that would quickly become one of his biggest mentors. Buddy Holly of The Crickets arranged Jenning’s first studio session before hiring him to play bass in his 1959 Winter Dance Party band.

After Holly’s tragic death in 1959, Jennings formed a rockabilly band named The Waylons. which ended up becoming the house band at a Scottsdale, Arizona, club called JD’s. He then started recording for the indie label Trent Records. But it wasn’t until he got Neil Reshen as his manager and moved to RCA Victor that he found success.

With RCA, Jennings released such critically acclaimed albums as Honky Tonk Heroes and Lonesome, on’ry and Mean.

Throughout the 1970s, Jennings was THE face of Outlaw country. Alongside Tompall Glaser, Jessi Colter, and Willie Nelson, Jennings recorded country music’s first platinum album, Wanted! The Outlaws in 1976.

He then branched out into appearing in films and television shows such as The Dukes of Hazard and even Sesame Street. For the former, he composed and performed the show’s iconic theme song as well as provided it’s narration.

In the early 80s, Jennings became hopelessly addicted to cocaine. The drug nearly killed him, but he was able to get clean in 1984. Afterwhich, he joined forces with Johnny Cash, Willie Nelson, and Kris Kristofferson to form the country supergroup The Highwaymen. That outfit released three award-winning albums between 1985 and 1995.

In the late 90s, Jennings slowed down on touring to spend more time with his family. His health was failing and he knew he didn’t have much time left to focus on the important things

After a lifetime of living like a rockstar and putting his body through about as much abuse as it could take. Jennings died in his sleep from complications of diabetes on the 13th of February, 2002, at the age of 64.

While Waylon Jennings certainly lived a very full life and accomplished much, he took one terrible regret to his grave. Join Facts Verse and Keep watching to learn what the painful secret was.

What Waylon Learned From Buddy Holly

Jennings once said that the main thing that he learned from Holly was attitude. Holly wasn’t willing to compromise when it came to his music. He was profoundly independent and always stayed true to his instincts.

Jennings, too, never let anyone boss him around or dictate what kind of music he should make. He was a true artist who made several landmark records that shifted the entire country music scene into new territory.

Jennings told the Country Music Hall of Fame in 1999 that Holly was the first person that ever had confidence in him. He went on to say that before he met Holly, he had about as much ‘star quality as an old shoe’. But Buddy Holly immediately took a liking to the young musician and never stopped believing in him.

Jennings landed his first big break when he invited to join Holly’s tour band. That milestone also proved to be one of the most significant turning points in his life and career.

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He Had A Seat On Buddy Holly’s Doomed Flight

By the late ’50s, Waylon Jennings one of the lucky West Texas musicians to find success in the music industry. By tapping into the previously unexplored sound that could found at the intersection of rock ‘n roll and country.

Buddy Holly was the poster boy of this burgeoning movement. He was a highly talented and savvy kid from Lubbock, Texas. Who took the nation by storm with songs like Peggy Sue and That’ll Be The Day.

After working with Waylon Jennings in the studio for his first recording session providing some backing guitar work. Holly burst into the KLLL studio where Waylon was working one day. Thrust a bass guitar at him and told him that he had two weeks to learn how to play it.

Buddy had been looking for someone to play bass with the Crickets for their 1959 Winter Dance Party Tour, but at the time, he had a little problem. The Crickets lacked members.

That meant that Holly had to quickly find backing musicians if he still wanted to do the tour he had already been booked for. Waylon Jennings certainly lived a very full life and accomplished much, he took one terrible regret to his grave.

In addition to Jennings, Holly hired Tommy Allsup on guitar and Carl Goose Bunch on drums. To prepare for the tour, Jennings listened to Holly’s entire catalog on repeat. He had very little time to work out all of the kinks. And he definitely didn’t want to disappoint one of his biggest heroes.Waylon Jennings certainly lived a very full life and accomplished much, he took one terrible regret to his grave. Join Facts Verse and Keep watching to learn what the painful secret was.

Although the tour welcomed by the young teenyboppers who no-doubt felt couped up during what was historically one of the coldest winters on record. It was hardly any fun for Holly. Jennings and the other musicians who spent the bulk of their time crammed like sardines into a frigid tour bus with a broken heater.

The infamous Winter Dance Party Tour, set up by Irving Field of General Artists Corporation, was going to feature The Big Bopper, Ritchie Valens, Dion and the Belmonts. And a relatively unknown singer from the Big Apple named Frankie Sardo. In addition to Holly and his Crickets as they bounced around the Midwest from January to February 1959.

To make matters worse, while traversing 300 miles between Green Bay, Wisconsin and Deluth, Minnesota, following their show on January 31, 1959, the tour bus broke down.

Sick and tired of the brutal conditions, Holly chartered a plane so that he wouldn’t have to spend another night sitting elbow to elbow with his fellow musicians as they puttered their way from Clear Lake, Iowa, to Moorhead, Minnesota.

Allsop and Jennings both agreed to shell out $36 for a chance to hitch a ride on Holly’s chartered flight so that they could arrive early and enjoy a night in a warm, cozy hotel bed and do a load of laundry. However, in the intermission at the Clear Lake, Iowa show, Richardson. Was able to convince Jennings to give up his seat on the plane.

The 250-pound man rightly called the Big Bopper. As such, he could barely squeeze himself into the narrow bus seat. He had also come down with the flu and desperately wanted to get some sleep to fight it off.

The last conversation that Jennings had with Holly involved the two exchanging playful jabs about their respective means of transportation. Holly told Jennings that he hoped his damn bus would freeze up again. While Jenning chided that he hoped Holly’s plane would crash.

At around 1 am on February 3, 1959, Holly and company’s flight took off from the nearby Mason City airport. Due to a deadly combo of pilot Roger Petersen’s lack of experience and the turbulent snowy conditions. The aircraft crashed into a field just a few minutes after take off.

Holly, Valens, Peterson, and Richardson were all killed instantly. Since then, that evening has come to be known as ‘the day the music died’.

Waylon Took The News Hard

Blaming himself for what had happened to his dear friend and mentor and kicking himself for those ominously foreboding parting words. Jennings hardly was able to make it through the final two weeks of the Winter Dance Party Tour.

After it was over, he turned down an offer to join the newly re-formed Crickets. Instead, he made his way back to Texas with the intention of hanging up his guitar and quitting music altogether.

However, time, as they say, heals all wounds, and eventually, Jennings was able to overcome all of that guilt and grief and returned back to his true calling. But he never forget the influence of his mentor, Buddy Holly. And how he took him under his wing and imparted some of the most valuable life lessons he ever learned. Their time together may have been brief, but it proved to be incredibly inspirational. Waylon Jennings certainly lived a very full life and accomplished much, he took one terrible regret to his grave. Join Facts Verse and Keep watching to learn what the painful secret was.

Waylon’s Last Show

Waylon Jenning’s health was already failing when he played his last major concert at the historic Ryman Auditorium in Nashville, Tennessee, in January 2000. He was backed by an all-star band called the Waymore Blues Band, who were made up of some of his favorite fellow musicians.

Jennings called the group the band he always wanted. He also was joined on stage by his beloved wife Jessi Colter and guest musicians Travis Tritt, Montgomery Gentry, and John Anderson.

The concert film Never Say Die: The Final Concert, which was recorded over two nights, documented this powerful and emotional performance. Jennings may have been been a bit more subdued than when he was in his prime. But he still put on one heck of a show while revisiting some of his classics like ‘I’m a Rambling Man’.’Good Hearted Woman’, and ‘I’ve Always Been Crazy’. Waylon Jennings certainly lived a very full life and accomplished much, he took one terrible regret to his grave.

To wrap up his career on the same fiercely independent note that he had always been known for. Jennings energetically performed the songs ‘Never Say Die’ and ‘Going Down Rocking’ before bidding his fans a heartfelt farewell.

Waylon Jennings may be gone, but he won’t soon be forgotten. Alongside the likes of Hank Williams, Jimmie Rodgers, and Ernest Tubb. Waylon will forever be remembered as being one of the last true Country legends. Waylon Jennings certainly lived a very full life and accomplished much, he took one terrible regret to his grave. Join Facts Verse and Keep watching to learn what the painful secret was.

Did you know that Waylon Jennings was supposed to be on the plane that went down, killing Buddy Holly, Richie Valens, and The Big Bopper? And do you think he was ever able to forgive himself for those ominous parting words he exchanged with Holly shortly before his death? Let us know in the comments.

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