Yes, Willie Nelson Can Act Too! Here Are His Most Iconic Roles

Texas’s greatest treasure and legendary, Willie Nelson, has been popping up in films since 1979. He played everything from a no-scruples music manager, a nasty outlaw to Willie Nelson as himself. It’s been a pretty exciting career for Nelson in the movies.

Though he thinks of himself as “the worst actor ever,” we totally beg to differ. Here are the most iconic roles of the Red Headed Stranger.

The Electric Horseman (1979)

Willie Nelson made his feature-film debut unforgettable, with lines: “I don’t know about you, but I’m gonna get me a bottle of tequila, find me one of them keno girls that can suck the chrome off a trailer hitch and just kind of kick back.” 

The country legend was a scene-stealer in his role as Wendell, the cowboy pal of washed-up rodeo champ Sonny Steele, enthusiastically played by Robert Redford. Whether cheering Steele to saddle up after one too many drunken nights or thinking over on how media folks — such as Jane Fonda’s Hallie Martin — use people to get what they want, Nelson’s character as Wendell was full of Western wisdom. 

Of course, director Sydney Pollack couldn’t bring a country star on his set and not find a reason to have him sing. When an argument turned heated between Steele and another rodeo pal, Wendell defused the situation by belting out a few bars with the most appropriate song for the scene, “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.”

Honeysuckle Rose (1980)

The movie told the story of touring country singer Buck Bonham, played by Nelson, as well as the threat to his marriage when the young daughter of his guitarist joined the tour and posed a temptation.

Though the Honeysuckle Rose isn’t much remembered except by the most loyal fans, renowned film critic, Roger Ebert, once said: “The movie is sly and entertaining, but it could have been better. Still, it has its charms, and one is certainly the presence of Willie Nelson himself.”

And perhaps the most memorable thing to come from the movie was the film’s soundtrack, “On the Road Again.” It was Nelson’s 27th studio album, and it made it to No. 1 on the U.S. Billboard Top Country Albums. It also won Willie Nelson, a Grammy for Best Country Song, and was nominated for Best Original Song at the 53rd Academy Awards. 

Barbarosa (1982)

In 1982, Willie Nelson starred as outlaw Barbarosa in an American Western film along with Gary Busey as naive Karl Westover.

Karl was a young cowboy who accidentally killed his brother-in-law and headed to Mexico to escape the consequences. Along the way, he encountered Barbarosa, who was also on the run. Barbarosa taught Karl survival skills for the desert — and how to rob. 

Barbarosa was filmed in an exotic wilderness, which gave the film’s outlaw story its strangeness and beauty. Although the film was written in 1973, the screenplay did not get much attention until Nelson read it seven years later. While he was only a few pages in, the singer decided, “I wanna be that guy.” He maintained that it was one of his favorite roles because “Barbarosa was just like me, misunderstood.”

Stagecoach (1986)

On May 18, 1986, Willie Nelson, together with Johnny Cash, Kris Kristofferson, and Waylon Jennings, appeared in a CBS-TV remake of the western movie “Stagecoach.” The four main stars of the film played as members of the country supergroup The Highwaymen.

Willie Nelson portrayed famous gunslinger and drunken dentist Doc Holliday. Johnny Cash portrayed Marshal Curly Wilcox, and Waylon Jennings played the gambler, Hatfield. The Highwaymen’s journey became more and more treacherous as the show went on.

Great soundtrack also played throughout the T.V. show. Willie sang the title song, which he has written with David Alan Coe, who also appeared in the movie, along with June Carter and other country faces you will recognize.

Miami Vice (1986)

Willie Nelson starred in the season premiere of Miami Vice, in an episode called ‘El Viejo,’ which meant ‘the old man.’ Nelson played a semi-bad guy in a Miami Vice who took the law into his own hands before biting the dust at the end of the show.

Miami Vice was set against the backdrop of Miami’s fast and furious Reagan Era drug war. Nelson was sporting a cowboy hat, bushy beard, bolo tie, and a poker-faced, thousand-yard-stare, as Jake Pierson. The mysterious Pierson was a rough-hewn retired Texas Ranger, living on a diet of cat food. He helped Crockett and Tubbs took down a Bolivian cocaine kingpin and his goons in a gunfight, taking a bullet in the process too. 

Red Headed Stranger (1986)

Red Headed Stranger, which also starred Katharine Ross and Morgan Fairchild, was based on Nelson’s 1975 album of the same name.

In the film, Nelson played Rev. Julian Shay, who traveled to Montana to preach, along with his wife. However, his wife left him for another man, and Julian Shay gunned her down. He then tried to find redemption for his actions.

Willie Nelson co-produced the project with William D. Wittliff, writer, and director of Red Headed Stranger. The original Red Headed Stranger’s director, Sam Peckinpah, left the project due to budget constraints. So the two men had to bankroll the film themselves. Most of the production, which took two months, occurred on Nelson’s Luck, Texas ranch and in other areas in central Texas. Nelson and Wittliff had previously worked together on the films Honeysuckle Rose and Barbarosa.

Wag the Dog (1997)

Willie Nelson starred alongside Dustin Hoffman and Robert De Niro in Wag the Dog. The film is an American political satire black comedy. It featured a spin doctor and a Hollywood producer who fabricated war in Albania to distract voters from a presidential sex scandal. 

Willie Nelson portrayed the role of a folk singer named Johnny Dean. As part of the hoax, Dean recorded a song called “Old Shoe.” The song was pressed onto a 78 rpm record, aged prematurely so that the listeners will think it was recorded years ago. It was sent to the Library of Congress to be “found.” Soon enough, several old pairs of shoes started appearing on phone and power lines, signs that the movement is taking hold.

The film was produced in 1997. It was a month before the outbreak of the Lewinsky scandal followed by the bombing of the Al-Shifa pharmaceutical factory in Sudan during the Clinton administration. This prompted the media to draw comparisons between the film and reality.

Half Baked (1998)

Willie Nelson made a brief cameo as a Historian Smoker in Half Baked, and it was a role he was born to play.  

He shared a joint with Thurgood and entertained him about the good ol’ days of legally pot smoking in the street. “It wasn’t the thing to do because it was the thing to do, you know? It was the thing to do because it got you high,” the historian said with weed-hazed wisdom. “You cool as shit, mister,” Thurgood replied. 

The Simpsons (2000)

Willie Nelson played an integral role in the year 2000 episode of ‘The Simpsons’ called “Behind the Laughter.” It’s a mockumentary of the way VH1 created Behind the Music. After 11 successful years on television, the family could not avoid the trappings of fame and success. Soon, they found themselves jailed, broke, and not speaking to each other.  

Nelson put on a phony awards show to bring them all back together, and it worked — or so it seemed. 

Monk (2002)

Willie Nelson appeared in the debut season of USA’s detective comedy Monk. His character was accused of murdering his manager when he discovered that he has been pocketing some of his concert earnings.

With the country star seemingly caught red-handed, it’s up to an unconvinced Monk to clear his name. Nelson absolutely had fun with his role – after all, he was playing himself, and the sly references to Willie’s famous pot smoking are inspired. But what really got fans high was when Nelson sang a solo version of “Blue Eyes Crying in the Rain.”

A Colbert Christmas: The Greatest Gift of All (2008)

The country star traded off his red bandanna into a Lawrence of Arabia headscarf as he appeared on Stephen Colbert’s holiday special. 

Though it was just a musical guest shot, Nelson was able to show off his acting chops. He sang the highly irreverent “The Little Dealer Boy” and even squared off with the Christmas-sweatered host.