Known as the Red-Headed Stranger, Willie Nelson (born April 30, 1933) is perhaps one of the most iconic CountryMusic 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: WaylonJennings, MerleHaggard, Julio Iglesias and RayCharles, among others. Although Nelson hasn't touched the Top 40 on his own since 1990, the occasional duet found its way onto the charts as late as 2003's "Beer for My Horses", with TobyKeith.
* BadassBeard: 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.
* ConceptAlbum: ''The Red-Headed Stranger'', chronicling the life of a man from Blue Rock, Montana.
* 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.
* [[RockstarSong Countrystar Song]]: "On the Road Again", natch.
* EarlyInstallmentWeirdness: 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 WaylonJennings: 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.
* FanNickname: The Red-Headed Stranger
* MoneyDearBoy: Thanks to a combination of his accountants from Price Waterhouse not paying his taxes for years and some bad investments in TheEighties, the IRS seized most of Nelson's assets in 1990, claiming he owed them $32 million. His attorney managed to negotiate a settlement down to $6 million, leading him to record ''The IRS Tapes: Who'll Buy My Memories?'' in 1992, a highly acclaimed double album performed by him alone on vocals and guitar, to pay off the debt.
* SignatureStyle: A reedy voice singing just off of the beat.
* TheStoner: He's the co-chair for National Organization for the Reform of Marijuana Laws. The occasional arrest for possession is another clue.
** According to legend, he once smoked a joint on the roof of the White House.
** And according to another legend, he once barged in out of nowhere on a ''Rolling Stone'' reporter interviewing BobDylan bearing a blunt as long as his forearm. The article was never written (according to the legend, anyway).
** TobyKeith penned a song titled "I'll Never Smoke Weed With Willie Again". And sings it in Willie's SignatureStyle.
* SuperGroup: The Highwaymen with Kris Kristofferson, WaylonJennings, and Music/JohnnyCash.