Whether playing a vengeful preacher in Red Headed Stranger or a killer version of himself on USA’s Monk, Willie Nelson is as at home in front of a camera as he is onstage. With a natural charisma and a drawling way with dialogue (his phrasing is as unique as the way he sings), Nelson has been casting bait for directors since Sydney Pollack first placed him opposite Robert Redford in 1979’s The Electric Horseman. We count down a dozen of his most memorable roles, including his epic 1986 Miami Vice appearance and — run for the border! — a Taco Bell commercial in 1991.
"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." With those lines, Willie Nelson made his feature-film debut unforgettable. Costarring as Wendell, the cowboy buddy of washed-up rodeo champ Sonny Steele, played with verve by Robert Redford, Nelson stole his scenes. Whether encouraging Steele to saddle up after one too many drunken nights or ruminating on how media folks — like Jane Fonda's Hallie Martin — use people to get what they want, Nelson's Wendell was full of Western wisdom. Of course, director Sydney Pollack couldn't have a country star on his set and not find a reason to have him sing. When an argument turns heated between Steele and another rodeo pal, Wendell defuses the situation by belting out a few bars of — what else? — "Mammas Don't Let Your Babies Grow Up to Be Cowboys."
While Willie ain’t likely to win Academy Awards for his acting chops, his classic "On the Road Again" did nab an Oscar nod for Best Original Song after appearing in the singer's 1980 silver-screen starring vehicle Honeysuckle Rose. The tender, time-stopping ballad "Angel Flying Too Close to the Ground" is all anybody needs to make a case for the film's shoo-in inclusion in this list. As for the millions-grossing, music-chocked film itself, it's pretty good, too. Country music's closest thing to Purple Rain (arguably), Rose tells the story of Nelson-esque (albeit slightly less successful) outlaw-country almost star Buck Bonham, whose domestic bliss is threatened by the temptations and rigors of the road. The film also gives fellow country luminaries the likes of Emmylou Harris, Johnny Gimble and the Family Band prime screen time along the way.
Nelson plays a horse-riding, pistol-twirling, double-braid-rocking outlaw in this overlooked western from 1982. Gary Busey, still fresh from his Academy Award-nominated turn in The Buddy Holly Story, is his bumbling sidekick, and writer William D. Wittliff — who also worked with Nelson on Honeysuckle Rose and Red Headed Stranger — handles the script. Barbarosa didn't exactly shoot 'em up at the box office, but the movie currently boasts a 100 percent score on Rotten Tomatoes — proof that it's aged rather well, much like ol' Willie himself.
Two decades before this movie's release, a young, cash-strapped Nelson sold one of his best songs, "Night Life," to a guitar instructor for $150. Whoops. Years later, he teamed up with fellow Highwayman Kris Kristofferson for this fierce, funny look into the seedy underbelly of the music industry. In the movie, a cash-strapped Willie (sound familiar?) goes toe-to-toe with shady promoters, flirts with young country ingenues and sings a lot of twangy tunes, often with help from Kristofferson… who just can't seem to button up his shirts. Art imitates life.
This remake of the John Wayne classic was released in May 1986, exactly one year after the Highwaymen's debut album hit shelves, and it more or less functions as a Western-themed commercial for the chemistry between Willie Nelson, Johnny Cash, Waylon Jennings and Kris Kristofferson. They're not the only country stars here, though. With additional cameos by June Carter, Jessi Colter and David Allan Coe, Stagecoach cracks its whip by focusing on country star power, not necessarily acting ability.
Nothing evokes words like "dated," "seminal" or "Lamborghini" quicker than über-sleek Eighties buddy cop series Miami Vice. But Willie Nelson is always Willie Nelson — timeless both in sound and style. Never is that more apparent than in the 1986 Vice episode "El Viejo." Set against the backdrop of Miami's fast and furious Reagan Era drug war (and a soundtrack of New Wave synthesizers), Nelson — sporting a cowboy hat, bushy beard, bolo tie and a stoic, thousand-yard-stare — plays Jake Pierson. A rough-hewn retired Texas Ranger who lives on a diet of cat food, the mysterious Pierson helps Crockett and Tubbs take down a Bolivian cocaine kingpin and his goons in a gunfight, taking a bullet in the process. Ever the cowboy, he shuffles off Miami's mortal coil in death scene worthy of Shane.
Nelson adapted his seminal 1975 album Red Headed Stranger for the big screen, playing the role of Reverend Julian Shay, a preacher who doesn't exactly practice what he, well, you know. Spurned by his lover, he becomes consumed with settling the score. The film's Western set, however, has held up better than the movie: Nelson built the entire production on his ranch outside of Austin. Dubbed "Luck, Texas," the town, with its own saloon, post office and church, has served as a retreat for the singer. Alas, the buildings were damaged during a recent storm, but Nelson has plans to restore and rebuild.
As it turned out, going on the road again, and again, and again… along with auxiliary income from film and TV cameos couldn’t keep the Red Headed Stranger from declaring bankruptcy after the IRS seized his assets for millions in unpaid back taxes in 1990. To make ends meet, in 1991 Nelson became the crackling voice of Taco Bell, singing passionately about the virtues of the steak burrito supremes and the like. Late, great comedian Bill Hicks, in a bit where he famously proclaimed, “Do a commercial, you’re off the artistic roll call,” made an exception for Willie, because his debt to The Man forced him to sell his soul. Overlook lyrics about running to the border to find love and zesty steak melts and, not unlike the Enchirito, the song Nelson croons in the commercial, “The Woman With the Rose Tattoo” is actually kinda good. Willie’s outlaw country comrade Johnny Cash also shilled for Taco Bell in the Nineties. Oh, how things have changed, as aligning with corporate brands has become part and parcel to life as a country star 20 years later.
The prophetic dark comedy Wag the Dog —released in 1997 — was a brilliant film and Nelson was undeniably brilliant in it. Playing ne'er-do-well songwriter Johnny Dean, Nelson helps drive home laughably nationalist sentiments with "found" country nuggets like "I Guard the Canadian Border" and "Good Old Shoe" — the faux old-timey soundtrack to America's equally fake war with Albania.
Like Marlon Brando as Vito Corleone, Half Baked's "Historian Smoker" (a.k.a. the "Should've Been There Smoker") is the role Willie Nelson was born to play. In the Nineties cult classic, Thurgood Jenkins (Dave Chappelle) and his stoner buds prevail upon the finest stash of medical marijuana New York City has ever seen, and stumble into the complex world of pot peddling. Willie "Historian Smoker" Nelson, a customer, makes a brief cameo to share a joint with Thurgood and regale him about the good ol' days of sanctioned pot smoking in the street and unprotected sex. "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 says with weed-hazed wisdom. "You cool as shit, mister," Thurgood replies. Hear, hear!
Who does America love more: Homer Simpson or Willie Nelson? Sure, famed musicians from Michael Jackson to Mick and Keith to Sonic Youth have made iconic, two-dimensional tour stops in Springfield over the course of their careers, but Nelson shares a kindred connection to Homer J. the rest don't. Without changing their ways, Homer and Willie each rack up a lifetime of unpredictable, amazing experiences and are loved unconditionally throughout. In "Behind the Laughter" — a 2000 episode telling the Simpsons' story in classic VH1 Behind the Music style — Nelson appears as himself (in voice-over form at least), bringing Springfield's most famous family back together at a fake awards show after the "staggering lows" of fame tear them apart.
Willie a killer? Say it ain't so! In the debut season of USA's detective comedy Monk, Nelson is accused of murdering his manager after discovering he has been pocketing some of his concert earnings. With the Red Headed Stranger seemingly caught red-handed, it's up to an unconvinced Monk to clear his name. Nelson looks like he's having fun with the role — he is playing himself after all — and the sly allusions to Willie's famous pot smoking are inspired. But what really got fans high was Nelson singing a solo version of "Blue Eyes Crying in the Rain" — with Tony Shalhoub's Monk backing him up on clarinet.
Nelson traded in his red bandanna for a Lawrence of Arabia headscarf when he appeared on Stephen Colbert's holiday special. Sure, it was a musical guest shot, but Nelson still had to flex his acting chops while singing the highly irreverent "The Little Dealer Boy" and squaring off with the Christmas-sweatered host. Especially when Colbert taunted him in a high falsetto: "You're really high/I'm going to tell your savior." But Nelson was unflappable, singing the three wise men spoof with all the seriousness he regularly brings to "Angel Flying Too Close to the Ground" or "Forgiving You Was Easy." Or maybe he was just stoned.