History Music / WillieNelson

** ''The Red-Headed Stranger'', chronicling the life of a man from Blue Rock, Montana.

* VitriolicBestBuds: With Waylon Jennings. Willie is pretty easy-going, but Waylon was fairly HotBlooded, and they kept getting into disagreements that would leave them apart for a while, then reunite for more music. A perfect example of this can be found in the biography "Willie Nelson: An Epic Life", which details an incident from the "Highwaymen" tour, where Waylon got the idea in his head that Willie was actively angling for higher billing/more money. Fortunately, the crew of the show were able to get him past this by simply pointing out "Waylon, it's ''Willie''. You really think he gives a crap about that kind of thing?". Sadly, they were in the middle of one of these "breaks" when Jennings died of complications from diabetes.

* ItWillNeverCatchOn: Willie's record label was convinced that ''Stardust'', his 1978 album of traditional pop standards, would never sell. It stayed on the charts for '''ten years'''.

* CoverAlbum: He's recorded a number of them. Notable examples include ''To Lefty from Willie'' (Lefty Frizzell songs), ''Stardust'' (traditional pop standards), ''Willie Nelson Sings Kristofferson'' (Music/KrisKristofferson songs), ''That's Life'' (Music/FrankSinatra songs).

* BrotherSisterTeam: His sister Bobbie was his full-time piano player from 1973 until her death in 2022. Besides being a fixture in his band, they did a few albums together as an official duo.

* ChristmasSongs: He's released two Christmas albums, ''Pretty Paper'' (1979) and ''Hill Country Christmas'' (1997, later reissued as ''Christmas with Willie Nelson'' and ''Willie Nelson's Classic Country Christmas''), with five songs from the former being re-recorded on the latter (which is a stripped-down affair largely featuring Willie on guitar and his sister Bobbie on piano). One of them was "Pretty Paper" itself, which is one of his best-known compositions, originally written in 1963 and turned into a hit that year by Music/RoyOrbison, even though it's really more of an AntiChristmasSong. The ''Pretty Paper'' album has one other original, an {{Instrumental}} called "Christmas Blues", while ''Hill Country Christmas'' has one original, the Tex-Mex style carol "El Niño", used as the album's {{Bookends}} with the vocal version at the beginning and an instrumental take at the end.

* ChristmasSongs: He's released two Christmas albums, ''Pretty Paper'' (1979) and ''Hill Country Christmas'' (1997, later reissued as ''Christmas with Willie Nelson'' and ''Willie Nelson's Classic Country Christmas''), with five songs from the former being re-recorded on the latter (which is a stripped-down affair largely featuring Willie on guitar and his sister Bobbie on piano). One of them was "Pretty Paper" itself, which is one of his best-known compositions, originally written in 1963 and turned into a hit that year by Music/RoyOrbison, even though it's really more of an AntiChristmasSong. The ''Pretty Paper'' album has one other original, an {{Instrumental}} called "Christmas Blues", while ''Hill Country Christmas'' has one original, called "El Niño", used as the album's {{Bookends}} with the vocal version at the beginning and an instrumental take at the end.

* ChristmasSongs:
** He's released two Christmas albums, ''Pretty Paper'' (1979) and ''Hill Country Christmas'' (1997).
** The title track from the former (which is also included in a different version on the latter) is one of his best-known compositions, originally written in 1963 and turned into a hit that year by Music/RoyOrbison, even though it's really more of an AntiChristmasSong.

* CoolOldGuy: In addition to being one of the legends of CountryMusic and American music in general, being known for his friendly and funny manner, and being TheStoner, he's also a practitioner of Kung Fu, and Tae Kwon Do, which he's held a black belt in since TheEighties. He's also a long-standing open supporter of gay rights, a stance not shared by many of his contemporaries throughout the decades and making him stand out further with younger generations.

One of country music's elder statesmen, and one of the very few artists from the '60s who is still around, Nelson is incredibly respected as a songwriter and lead guitarist, while his iconic jazzy singing style is instantly recognizable.

Nelson was at the top of his game for most of the 1970s and '80s, charting both as a solo singer and as a duet partner with... well, almost everybody: Music/WaylonJennings, Music/MerleHaggard, Julio Iglesias and Music/RayCharles, among others. He and Jennings are considered two of the original "{{outlaw country|Music}}" artists. Although Nelson hasn't touched the Top 40 on his own since 1990, the occasional duet has found its way onto the charts as late as 2003's "Beer for My Horses", with Music/TobyKeith.

* SexinessScore: "Ten With a Two" is about a drunk guy who's approached by a woman who he perceives as "a 10" due to BeerGoggles, only realizing after a BedmateReveal in the morning that she's actually a "2". When it was released as a single in summer 1991, the song gained some notoriety due to criticism from conservatives and womens' groups for what they viewed as demeaning lyrics toward "less than perfect" women--in other words, that the song was really about a man disparaging ugly women as having no social, romantic or other redeeming values.

* SexinessScore: "Ten With a Two" is about a drunk guy being approached by an ugly woman whom he perceives as "a 10" due to BeerGoggles, and only in the morning after he has a BedmateReveal and realizes she's actually a "2". When it was a single in summer 1991, the song gained some notoriety due to criticism from conservatives and womens' groups for what they viewed as demeaning lyrics toward "less than perfect" women--in other words, that the song was really about a man disparaging ugly women as having no social, romantic or other redeeming values.

* SexinessScore: "Ten With a Two" is about a drunk guy being approached by an ugly woman whom he perceives as "a 10" due to BeerGoggles, and only in the morning after he has a BedmateReveal and realizes she's actually a "2". When it was a single in summer 1991, the song gained some notoriety by conservative and women's groups for what they viewed as demeaning lyrics toward "less than perfect" women--in other words, that the song was really about a man disparaging ugly women as having no social, romantic or other redeeming values.

** The title track from the former (which was also given a new rendition on the latter) is one of his best-known compositions, originally written in 1963 and turned into a hit that year by Music/RoyOrbison, even though it's really more of an AntiChristmasSong.

* CoverAlbum: He's recorded a number of them. Notable examples include ''To Lefty from Willie'' (Lefty Frizzell songs), ''Stardust'' (traditional pop standards), ''Willie Nelson Sings Kristofferson'' (Music/KrisKristofferson songs), ''That's Life'' (Music/FrankSinatra songs)

* SuperGroup: The Highwaymen with Creator/KrisKristofferson, Music/WaylonJennings, and Music/JohnnyCash.
* TwelveBarBlues: "Shotgun Willie", while unquestionable country, is written with this structure.

* ItWillNeverCatchOn: Willie's record label was convinced that "Stardust", his 1978 album of pop standards, would never sell. It stayed on the charts for '''ten years'''.