Rep. Beto O'Rourke, D-El Paso, joined by singer Willie Nelson, waves to supporters at a campaign rally at Auditorium Shores on Sept. 29, 2018 in Austin.

Rep. Beto O'Rourke, D-El Paso, joined by singer Willie Nelson, waves to supporters at a campaign rally at Auditorium Shores on Sept. 29, 2018 in Austin.

Drew Anthony Smith/Getty Images

When Willie Nelson announced last month he'd headline a benefit concert in Austin for liberal Senate candidate Beto O'Rourke, some of his fans went ballistic on social media and implied he should shut up and sing and leave politics out of it.

Leave politics out of it? As his longtime fans know, the soft-spoken Nelson speaks his mind on just about everything, including politics. And while he may be the Red Headed Stranger, his political views definitely lean blue.

In advance of Willie's concerts at Billy Bob's Texas on Nov. 16 and 17, here's a look at Willie's five biggest political moments:

Supporting marijuana legalization (late 1960s to present)

Willie Nelson to launch new line of cannabis products, starting with coffee

Nelson was an outspoken Pied Piper of pot legalization back when marijuana was still considered the devil's weed by a lot of people. Today he's a bona fide pot-repreneur, with a brand of legal cannabis called "Willie's Reserve." But early in his career, Nelson's pro-ganja stance made him an outsider among conservative country music fans who sang, "We don't smoke marijuana in Muskogee" every time Merle Haggard's 1969 hit, "Okie From Muskogee," came on the jukebox.

Sparking one up at Jimmy Carter's White House (1980)

A vocal Carter fan, Nelson played a White House concert for the Prez and even sang a duet with Rosalynn Carter on "Up Against The Wall Redneck Mother." Later that night, the singer and a White House aide climbed to the White House roof and smoked a spliff: While the two "joint" chiefs of staff gazed dreamily at the Washington Monument, Carter was busy downstairs working on his failed re-election bid.

Protesting the Persian Gulf and Iraq Wars (1990 and 2003)

Although he's not really a protest singer, Nelson is a die-hard peacenik who frequently speaks out against U.S. military campaigns. The Persian Gulf War spurred him to pen "Jimmy's Road," a song about a soldier who dies in combat, while the Iraq War inspired "Whatever Happened to Peace on Earth?" in which Nelson asks, "How much oil is one human life worth?"

Supporting Dennis Kucinich for president (2004)

Nelson fans who are shocked by his endorsement of a long-shot liberal like O'Rourke must have forgotten the 2004 presidential election, when the singer performed benefit concerts for Kucinich, the long-shot progressive from Ohio. "Whether he's electable or not, who knows? I just like him because he tells the truth," the singer told reporters at the time.

Supporting gay rights (2006)

Inspired by the success of Brokeback Mountain, Nelson recorded Ned Sublette's obscure "Cowboys Are Frequently Secretly Fond of Each Other," with its lyric "Inside every man there's the feminine." "The song's been in the closet for 20 years. The timing's right for it to come out," a playful Nelson said at the time. Former News music critic Mario Tarradell described it as the first gay-themed song ever released by a major country artist. Three years later, Nelson was back at it, poking fun at homophobia with a comic rebuttal to "Cowboys" titled "Ain't Goin' Down on Brokeback Mountain."

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