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* GermansLoveDavidHasselhoff: Waylon was on the level of Elvis and The Rolling Stones with the Navajo Nation. His song "Love Of The Common People" is often touted as the unofficial anthem of the Nation.

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* GermansLoveDavidHasselhoff: Waylon was on the level of Elvis and The Rolling Stones with the Navajo Nation. His song "Love Of The Common People" is often touted as the unofficial anthem of the Nation.Nation.
* HarsherInHindsight: Once jokingly told ''Music/BuddyHolly'' that he hopes the latter's plane crashes, in response to another joke from Buddy about how he hopes the former's bus freezes up. Waylon's joke had haunted him for the rest of his life after Buddy's plane ''did'' indeed crash.

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* CoveredUp: His Music/WillieNelson duet "Mamas Don't Let Your Babies Grow Up to Be Cowboys" was first released by Ed Bruce. Similarly, their "Good Hearted Woman" was originally a Top Ten single for Jennings solo, but the duet version was a #1.

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* CoveredUp: His Music/WillieNelson duet "Mamas "Mammas Don't Let Your Babies Grow Up to Be Cowboys" was first released by Ed Bruce.Bruce, and co-written by Bruce and his wife Patsy. Similarly, their "Good Hearted Woman" was originally a Top Ten single for Jennings solo, but the duet version was a #1.


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* DoNotDoThisCoolThing:
** "Mammas Don't Let Your Babies Grow Up To Be Cowboys" goes out of its way to depict cowboys as a [[TheSoftHeartedWarrior blend of machismo and sensitivity]], only to warn in its chorus:
--->Mammas, don't let your babies grow up to be cowboys\\
Don't let 'em pick guitars or drive them old trucks\\
Let 'em be [[BoringButPractical doctors and lawyers and such]]
** "I'm a Ramblin Man" has the narrator brag about how well-traveled he is and how exciting his life has been, but then advises "Don't fall in love with a ramblin' man."
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* EpicRiff: "I'm a Ramblin' Man" and "Rainy Day Woman" are rare classic country examples of this; "Rainy Day Woman"'s riff is played on a ''steel'' guitar.

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* EpicRiff: "I'm a Ramblin' Man" and "Rainy Day Woman" are rare classic country examples of this; "Rainy Day Woman"'s riff is played on a ''steel'' guitar.guitar.
* GermansLoveDavidHasselhoff: Waylon was on the level of Elvis and The Rolling Stones with the Navajo Nation. His song "Love Of The Common People" is often touted as the unofficial anthem of the Nation.
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** Also on the receiving end: he recorded "Where Corn Don't Grow" in 1990 but it only got to #67 on the country chart. 6 years later it became a Top 10 hit for Travis Tritt.

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** Also on the receiving end: he recorded "Where Corn Don't Grow" in 1990 but it only got to #67 on the country chart. 6 years later it became a Top 10 hit for Travis Tritt.Music/TravisTritt.
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* CoveredUp: His WillieNelson duet "Mamas Don't Let Your Babies Grow Up to Be Cowboys" was first released by Ed Bruce. Similarly, their "Good Hearted Woman" was originally a Top Ten single for Jennings solo, but the duet version was a #1.

to:

* CoveredUp: His WillieNelson Music/WillieNelson duet "Mamas Don't Let Your Babies Grow Up to Be Cowboys" was first released by Ed Bruce. Similarly, their "Good Hearted Woman" was originally a Top Ten single for Jennings solo, but the duet version was a #1.
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* EpicRiff: "I'm a Ramblin' Man" is a rare classic country example of this.

to:

* EpicRiff: "I'm a Ramblin' Man" is a and "Rainy Day Woman" are rare classic country example examples of this.this; "Rainy Day Woman"'s riff is played on a ''steel'' guitar.
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** Also on the receiving end: he recorded "Where Corn Don't Grow" in 1990 but it only got to #67 on the country chart. 6 years later it became a Top 10 hit for Travis Tritt.

to:

** Also on the receiving end: he recorded "Where Corn Don't Grow" in 1990 but it only got to #67 on the country chart. 6 years later it became a Top 10 hit for Travis Tritt.Tritt.
* EpicRiff: "I'm a Ramblin' Man" is a rare classic country example of this.
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** "Clyde", originally a J.J. Cale album track.

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* CoveredUp: His WillieNelson duet "Mamas Don't Let Your Babies Grow Up to Be Cowboys" was first released by Ed Bruce. Similarly, their "Good Hearted Woman" was originally a Top Ten single for Jennings solo, but the duet version was a #1.

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\n* CoveredUp: His WillieNelson duet "Mamas Don't Let Your Babies Grow Up to Be Cowboys" was first released by Ed Bruce. Similarly, their "Good Hearted Woman" was originally a Top Ten single for Jennings solo, but the duet version was a #1.#1.
** "I'm a Ramblin' Man", originally written and recorded by Ray Pennington (who produced Waylon's version).
** Also on the receiving end: he recorded "Where Corn Don't Grow" in 1990 but it only got to #67 on the country chart. 6 years later it became a Top 10 hit for Travis Tritt.

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