Known for his rugged individualism and for helping popularize the grittier, rock-infused
genre known as outlaw country, Waylon Jennings was 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 the 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
its 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 certainly lived a very full life and accomplished much, he took one terrible
regret to his grave.
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 was 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 was one of the lucky West Texas musicians to find
success in the music industry by tapping into the previously unexplored sound that could
be 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.
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.
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.
Although the tour was 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.
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 was 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 the 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'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'.
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.
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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