Known as the Red-Headed Stranger, Willie Hugh Nelson (born April 29, 1933) is perhaps one of the most iconic Country Music artists of the 20th century. He started his career in the 1950s, playing bass guitar for Ray Price and writing songs for others (ever heard of "Crazy" by Patsy Cline?). A modest #10 hit in 1962 ("Willingly"), first brought him to the charts, but it wasn't until 1975 that he broke through with the massive crossover hit "Blue Eyes Crying in the Rain". For most of the 1970s and 1980s, Nelson was at the top of his game, charting both as a solo singer and as a duet partner with... well, almost everybody: Waylon Jennings, Merle Haggard, Julio Iglesias and Ray Charles, among others. 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 Toby Keith. One of country music's elder statesmen, and one of the very few artists from the 60's who is still around, Nelson is incredibly respected as a songwriter and lead guitarist, while his iconic jazzy singing style is instantly recognizable.
- As Himself: In guest appearances on Swing Vote, Broken Bridges, Beerfest, Monk, The Country Bears, The Simpsons (voice), Austin Powers: The Spy Who Shagged Me, and King of the Hill (voice).
- Badass Beard: Since Shotgun Willie, he's had one. His prior albums look quite strange with him clean shaven.
- It's a major plot point for the underrated Western Barbarosa where he plays the eponymous cowboy hero.
- Christmas Songs: He's released two Christmas albums, Pretty Paper (1979) and Hill Country Christmas (1997).
- Concept Album: The Red-Headed Stranger, chronicling the life of a man from Blue Rock, Montana.
- Before that, Yesterday's Wine (about a man's life from birth to death) and Phases and Stages (about the breakup of a marriage).
- Cool Old Guy: In addition to being one of the legends of Country Music and American music in general, being known for his friendly and funny manner, and being The Stoner, he's also a practitioner of Kung Fu, and Tae Kwon Do, which he's held a black belt in since The '80s.
- Countrystar Song: "On the Road Again", natch.
- The Cover Changes the Meaning: The majority of the songs on Red Headed Stranger are older songs that are used to illustrate the album's story arc.
- Defeating the Undefeatable: Is the only person known to have out-smoked Snoop Dogg.
- Early Installment Weirdness: His earliest material is fairly straight classic country (though his sophisticated lyrics were considered cutting edge). When he recorded with RCA Records in the late 60s he had the same problem as his labelmate Waylon Jennings: his style was too eclectic to fit into the usual Nashville formulas, leading to experiments with crooning ballads ("She's Not For You"), pop ("I'm a Memory") and even gospel ("Laying My Burdens Down"). He also sang with a clipped, over-enunciated style that stands in contrast to his later signature jazzy phrasing.
- He looked completely different, too. Yes, this suit-clad, impeccably groomed, clean-shaven guy is Willie.
- Empty Chair Memorial: Riderless horse variant; namely, the bay pony that accompanies the Red-Headed Stranger in the eponymous song was his deceased wife's horse. He shoots and kills a woman who tries to steal it, and went free, because "you can't hang a man for killing a woman who's trying to steal his horse."
- Listing Cities: "Texas in My Soul"
- New Sound Album: He'd already been moving in that direction for years, but Shotgun Willie marked the point where he finally broke away from the Nashville establishment and started playing his own unique brand of music.
- Signature Style: A reedy voice singing just off of the beat, and jazz-flavored guitar lines played on a nylon-string acoustic(instead of a steel-string like virtually all other popular music).
- The Stoner: He's the co-chair for National Organization for the Reform of Marijuana Laws. The occasional arrest for possession is another clue.
Willie: Stephen, right now, I'm so high, you're hallucinating.
- According to legend, he once smoked a joint on the roof of the White House. In a recent Rolling Stone interview, he claimed(while winking at the interviewer) that he couldn't remember doing this.
- And according to another legend, he once barged in out of nowhere on a Rolling Stone reporter interviewing Bob Dylan bearing a blunt as long as his forearm. The article was never written (according to the legend, anyway).
- Brought up in A Colbert Christmas: The Greatest Gift of All!:
- Super Group: The Highwaymen with Kris Kristofferson, Waylon Jennings, and Johnny Cash.
- Ten with a Two: Trope Namer, from his 1990 song "Ten with a Two".