Willie Nelson

Known as the Red-Headed Stranger, Willie Nelson (born April 30, 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 found its way onto the charts as late as 2003's "Beer for My Horses", with Toby Keith.

Tropes present:

 * Badass Beard: He's always had one.
 * Actually, not always: In fact, for his first decade and a half in music, he was clean-shaven (as evidenced in one of his early albums). The beard didn't show up until "Shotgun Willie", which coincidentally was when he changed to the Outlaw Country style we know him for today.
 * It's a major plot point for the underrated Western Barbarosa where he plays the eponymous cowboy hero.
 * Blue Eyes: ...crying in the rain.
 * 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 Eighties.
 * Countrystar Song: "On the Road Again", natch.
 * Fan Nickname: The Red-Headed Stranger
 * Signature Song: The aforementioned "Always on My Mind," "My Heroes Have Always Been Cowboys," "Angel Flying Too Close to the Ground," and of course, "On the Road Again." Really, who doesn't know that one?
 * The Stoner: 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 Bob Dylan bearing a blunt as long as his forearm. The article was never written (according to the legend, anyway).
 * Toby Keith penned a song titled "I'll Never Smoke Weed With Willie Again". And sings it in Willie's Signature Style.