Biography: Waylon Jennings

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We've had the chance to feature three of the four Highwaymen on our Live in Texas program and now we are proud to present the fourth and final member: country legend Waylon Jennings!


Waylon Jennings was one of the founding members of Outlaw Country.


Wayland Arnold Jennings was born and raised in Littlefield, TX.  Born in June of 1937, his mother Lorene changed his name to Waylon after learning of Wayland Baptist University in Plainview and did not want people associating her son with that institution.  Lorene gave the young Waylon his first guitar and his first guitar lessons when he turned eight.  By twelve, he had his own thirty minute spot on the local radio station, KVOW.  Shortly after, he would form his first band, the Texas Longhorns.


Jennings was briefly one of Buddy Holly's Crickets - and a close friend.


At seventeen, he would drop out of high school and move to Lubbock where he would join up with Buddy Holly at KLLL Radio.  Holly would produce two singles for Waylon: "Jolie Blon" and "When Sin Stops (Love Begins)".  Waylon was in good company - along with Holly and Tommy Allsup on guitar, a young King Curtis can be heard playing sax on the singles.  Jennings joined Holly's backing band, the Crickets, on bass guitar and would hit the road with him and other rock 'n roll stars Ritchie Valens and J. P. "The Big Bopper" Richardson.  Unfortunately, the tour would claim the lives of Holly, Valens, and Richardson as their charter plane would crash near Clear Lake, Iowa, on February 3rd, 1959.  That dark day would later be immortalized as "The Day the Music Died".  According to Jennings, he gave up his seat on that plane to a sick Richardson as an act of kindness and jokingly told Holly that "...I hope your ol' plane crashes!", a phrase that he would regret saying the rest of his life.


Folk-Country was Jenning's first collaboration with producer Chet Atkins.


After the death of his close friends, Jennings returned to KLLL in Lubbock and continued to work as a DJ and record music.  He moved to Arizona in 1960 and put together a rockabilly band, the Waylors, and eventually signed with Los Angeles based A&M Records.  Success evaded Jennings and by 1964 he was released from A&M after creative differences.  Luckily, he found a new home at RCA Records in Nashville and released his debut album Folk-Country in 1966.  A modest success, it would be followed by Leavin' Town and Nashville Rebel, the latter of which was the soundtrack to a movie starring Jennings of the same name.  It was during this time that he began his life long friendship with fellow musician Johnny Cash as the two would become roommates and would share frustration about the infamously straight-laced Nashville music scene.


Ladies Love Outlaws paved the way for the Outlaw Country movement.


Even as Jennings became less and less happy about the lack of creative control over his music, he started producing Top 40 Country hits regularly starting with "Stop the World (And Let Me Off)" from the aforementioned Folk-Country at #16 and cracked the Top 10 with "(That's What You Get) For Lovin' Me" at #9 in 1967.  He would climb even higher on the country charts with his 1968 single "Only Daddy That'll Walk the Line" which reached #2 (and became his first #1 song in Canada).  Working with another young, struggling songwriter named Kris Kristofferson, the duo would ultimately create two albums that would be the forerunners to the Outlaw Country sound that would make both of them famous just a few years later: Singer of Sad Songs (1970) and Ladies Love Outlaws (1972).


Kristofferson, Nelson, and Jennings were based out of Austin during the early 70s.


Shortly after the release of Ladies Love Outlaws, Jennings was afflicted with Hepatitis and was in the hospital for some time.  After his release, he renegotiated his contract with RCA to have complete artistic control and began collaborating with a singer/songwriter signed to Atlantic Records named Willie Nelson.  1973 would be a big year for not just Waylon, but for all of country music: his albums Lonesome, On'ry and Mean and Honky Tonk Heroes would be critical and commercial successes that put Outlaw Country on the map (as well as the then-unknown Billy Joe Shaver, who wrote many of the tracks).  1974 would put Jennings even closer to the top - his This Time and The Ramblin' Man albums would have their title tracks become the #1 country songs in America.  Another single, "Rainy Day Woman", would reach #2.  The following year, Dreaming My Dreams would include another #1 country single, "Are You Sure Hank Done It This Way", which also peaked at #49 on the pop charts.  Although it did not chart itself, another single from that album would go on to be one of the most famous country songs of all time: "Bob Wills Is Still the King".  The Country Music Association would also award Jennings the Male Vocalist of the Year Award during this time.


Country music's first platinum album included poet Shel Silverstein as a producer.


The next few years would see Jennings at the top of his game.  In 1976, Jennings would go against RCA and record Are You Ready For The Country at his own expense in Los Angeles with the Waylors as his backing band.  The album would become the #1 country album in America three different times over the next year, would be certified gold, and would be named Country Album of the Year by Record World Magazine.  However, as well received as Are You Ready was, it paled in comparison to his compilation album with Willie Nelson, Jessi Coulter, and Tompall Glaser: Wanted! The Outlaws.  This album, featuring previously released material, would become country music's first platinum album ever.  It became a #1 country album, a #10 pop album, and spawned two hit singles: "Suspicious Minds" and "Good Hearted Woman".  1976 would also have the release of the #1 Waylon Live album.


Waylon & Willie spent 10 weeks at the top of the charts.


1977 was another great year for Jennings.  Ol' Waylon would be another #1 country album and included another of his most famous songs - a duet with Nelson called "Luckenbach, Texas (Back to the Basics of Love)".  Ironically, even though he wrote the song, Jennings disliked it and reportedly told his drummer, "Next time when I record a song, you remind me I have to sing that sumbitch the rest of my life".  Another album, again with Nelson as his partner, would be released in 1978 to great success: Waylon & Willie.  The album would be another #1 country hit, would earn the duo a Grammy, and featured another indispensable country classic, "Mammas Don't Let Your Babies Grow Up to Be Cowboys".  I've Always Been Crazy would also be released in 1978, would be another #1 country album, and made it quite clear that Jennings felt the whole Outlaw Country thing had been played out past its prime.  1979 would see the release of What Goes Around Comes Around which peaked at #2.


Shooter Jennings is a respected musician in his own right!


With the onset of the 1980s, Jennings still had a lot of success ahead of him.  He released another #1 country album, Music Man, in 1980.  The album featured the hit theme song from The Dukes of Hazzard.  Several other hit albums followed: Black on Black (1982), WWII (1982), and Take It to the Limit (1983).  The latter two would be duet albums with Nelson.  Unfortunately, by this time Jenning's legendary cocaine use had spiraled completely out of control and was reportedly costing him over $1,500 a day to maintain.  His music began to suffer and albums like It's Only Rock and Roll and Waylon and Company would only reach #10 and #12 on the country charts, respectively.  With the help of his son Shooter Jennings, he finally quit coke in 1984.


Here is Jennings alongside Big Bird in one of his most famous cameos.


After cleaning up his act, Jennings joined with Kris Kristofferson, Willie Nelson, and Johnny Cash in 1985 to form the country supergroup known as the Highwaymen.  Their debut album, Highwayman, went Platinum.  After leaving RCA Records, Jennings had one more #1 album up his sleeve: the 1986 Will the Wolf Survive.  After Wolf, his music began charting less and eventually fell off the charts altogether.  However, after 25 #1 singles to his name, he continued having no problem filling any venue.  While he was not on the road, he spent some time acting and making guest appearances on television and in movies.   For instance, he played a singing truck driver along side Big Bird in Sesame Street Presents Follow That Bird.  He also appeared with the rest of the Highwaymen in the 1986 remake of Stagecoach.


Waylon Jennings: musical giant.


After the release of the second Highwaymen album, Highwayman II, Jennings was still performing but was gradually slowing down due to health issues.  In 1988, he had undergone heart bypass surgery and was eventually diagnosed with diabetes.  Even with poor health, he performed at music festivals like Lollapalooza in the late 90s and drew giant crowds.  In 1997, he semi-retired.  Regretting setting a poor example for his children by not finishing highschool, he got his GED.  Not done performing, he put together a 13 man "dream team", largely comprised of former Waylors, and performed sporadically until 2001.  In 2000, he recorded his last album at Ryman Auditorium in Nashville, Never Say Die: Live.  Complications from his diabetes forced an emergency surgery that led to the removal of his foot in 2001.  After this, he retired to his home in Arizona and passed away on February 13th, 2002 at the age of 64.  With his contributions to country, rock, and folk music, he is remembered among the music giants he idolized like Bob Wills, Hank Williams, and Elvis Presley, as well as his contemporaries Willie Nelson and Johnny Cash.  If you want to learn more about Waylon, we suggest you visit his homepage here.



(1964) JD's

(1966) Folk-Country - #9

(1966) Leavin' Town - #3

(1966) Nashville Rebel - #4

(1967) Waylon Sings Ol' Harlan - #32

(1967) Love of the Common People - #3

(1967) The One and Only - #19

(1968) Hangin' On - #9

(1968) Only the Greatest - #12

(1968) Jewels - #6

(1969) Just to Satisfy You - #7

(1969) Country-Folk (with the Kimberlys) - #13

(1970) Waylon - #14

(1970) Singer of Sad Songs - #23

(1971) The Taker / Tulsa - #12

(1971) Cedartown, Georgia - #27

(1972) Good Hearted Woman - #7

(1972) Ladies Love Outlaws - #11

(1973) Lonesome, On'ry and Mean - #8

(1973) Honky Tonk Heroes - #14

(1974) This Time - #4

(1974) The Ramblin' Man - #3

(1975) Dreaming My Dreams - #1

(1976) Are You Ready for the Country - #1

(1976) Wanted! The Outlaws (with Willie Nelson, Jessie Colter, and Tompall Glasser) - #1

(1976) Waylon Live - #1

(1977) Ol' Waylon - #1

(1978) I've Always Been Crazy - #1

(1978) Waylon & Willie (with Willie Nelson) - #1

(1978) White Mansions (with Jessie Colter, John Dillon, and Steve Cash)

(1979) What Goes Around Comes Around - #2

(1979) Greatest Hits - #1

(1980) Music Man - #1

(1982) Black on Black - #3

(1982) WWII (with Willie Nelson) - #3

(1982) Leather and Lace (with Jessi Colter) - #11

(1983) It's Only Rock + Roll - #10

(1983) Waylon and Company - #12

(1983) Take it to the Limit (with Willie Nelson) - #3

(1984) Never Could Toe the Mark - #20

(1985) Turn the Page - #23

(1985) Highwayman (with the Highwaymen) - #1

(1986) Sweet Mother Texas

(1986) Will the Wolf Survive - #1

(1986) Heroes (with Johnny Cash) - #13

(1987) Hangin' Tough - #19

(1987) A Man Called Hoss - #22

(1988) Full Circle - #37

(1990) The Eagle - #9

(1990) Highwayman 2 (with the Highwaymen) - #4

(1991) Clean Shirt (with Willie Nelson) - #28

(1992) Too Dumb for New York City, Too Ugly for LA - #70

(1992) Ol' Waylon Sings Ol' Hank

(1993) Cowboys, Sisters, Rascals & Dirt

(1994) Waymore's Blues (Part II) - #63

(1995) The Road Goes On Forever (with the Highwaymen) - #42

(1996) Right for the Time

(1998) Closing in on the Fire - #71

(1998) Old Dogs (with Bobby Bare, Jerry Reed, and Mel Tillis) - #61


Songs on KBEC:

"Amanda" - #1

"America" - #6

"Are You Ready for the Country" - #7

"Are You Sure Hank Done It This Way" - #1

"Bob Wills Is Still the King"

"Brown Eyed Handsome Man" - #3

"Can't You See" - #4

"Clyde" - #7

"Drinkin' and Dreamin'" - #2

"Fallin' Out" - #8

"Highwayman" (with the Highwaymen) - #1

"I Ain't Living Long Like This" - #1

"I'm a Ramblin' Man" - #1

"I've Always Been Crazy" - #1

"Just to Satisfy You" (with Willie Nelson) - #1

"Ladies Love Outlaws"

"Lucille (You Won't Do Your Daddy's Will)"

"Luckenbach, Texas (Back to the Basics of Love)" (with Willie Nelson) - #1

"Mammas Don't Let Your Babies Grow Up to Be Cowboys" (with Willie Nelson) - #1

"Only Daddy That'll Walk the Line" - #2

"Rainy Day Woman" - #2

"Rose in Paradise" - #1

"Rough and Rowdy Days" - #6

"Shine" - #1

"Sweet Dream Woman" - #7

"(That's What You Get) For Lovin' Me" - #9

"The Eagle" - #22

"The Taker" - #5

"The Wurlitzer Prize (I Don't Want to Get Over You)" - #1

"Theme from the Dukes of Hazzard (Good Ol' Boys)" - #1

"This Time" - #1

"Waymore's Blues"

"Women Do Know How to Carry On" - #4

"Wrong" - #5