Gus Van Sant seems nervous.

On a warm June night, the director is back in Portland, the city that long served as his home, and muse. Don't Worry, He Won't Get Far on Foot, his biopic of Portland cartoonist John Callahan, didn't open nationally until this week, but it's showing early at Cinema 21 as part of a fundraiser put on by Amazon Studios and Willamette Week, with proceeds going toward John Callahan Garden, located only a few blocks north.

It's a star-studded event, at least by Portland standards. Courtney Taylor-Taylor and Zia McCabe of the Dandy Warhols are there, along with singer Beth Ditto, who makes her acting debut in the movie.

Mostly, though, the audience is made up of the people who knew Callahan best—folks from The Dalles, where he grew up, and graying Old Portlanders who remember him from his days haunting this very neighborhood, zipping down Northwest 21st Avenue in his motorized wheelchair.

Expectations with this group are particularly high—they've been hearing about this movie for 20 years, going back to when Robin Williams was attached to play the lead role.

When he's called forward to say a few words before the film begins, it takes Van Sant a couple awkward seconds to materialize from the lobby.

"I think there are 250 Callahans here," he quips when he finally makes it to the microphone. And then, as if to warn the audience: "A lot of things aren't quite the real John. They're our interpretation."

Callahan (Jenna Biggs)
Callahan (Jenna Biggs)

But the director perhaps has other reasons to feel nervous than just the room in front of him.

The past decade, to put it kindly, has not been one of Van Sant's best.

Once regarded as a pioneer of raw, emotional independent cinema, Van Sant first emerged on the national radar with a trio of films set in Portland, where he attended Catlin Gabel School as a teenager and eventually settled in the 1980s. His movies since have ranged from mainstream crowd-pleasers like Good Will Hunting, which grossed more than $200 million worldwide, to more personal, experimental projects.

But over the past 10 years, Van Sant has slipped into making, in the words of one critic, "increasingly small and irrelevant art movies." His past three films received the worst reviews of his career—the last one was even booed at Cannes, the festival that had previously awarded him the prestigious Palme d'Or for Elephant, his haunting film about a high school shooting in Portland.

"Something happens in Hollywood when you have a bomb, or a string of bombs, where they put you in movie jail," says Variety film critic Peter Debruge. "It means, suddenly, your name goes from being on a shortlist of directors people want to work with to the list nobody calls."

Gus Van Sant
Gus Van Sant

So, while Don't Worry is a small film, with modest commercial expectations, for Van Sant the movie carries more baggage than it might appear.

Callahan is dead now, having succumbed in 2010, at age 59, to respiratory ailments related to his quadriplegia. Now, about the only trace you can find of him in Portland is a small courtyard on the campus of Legacy Good Samaritan Medical Center, where he was once a patient, in his old neighborhood of Northwest Portland. A path through the garden is lined with dozens of his drawings—the ones appropriate for public display, anyway.

But when he was alive, it was hard to avoid John Callahan if you lived in Portland.

For 27 years, if you opened Willamette Week, you'd find one of his cartoons, needling polite society with jokes about feminists, lesbians, nuns, doctors, lawyers, the homeless, conservatives, liberals and his fellow "quads."

(John Callahan)
(John Callahan)

Callahan pissed off many in his day. The cartoonist, who was paralyzed in a car accident at age 21, made a career of pushing buttons, testing boundaries and immolating all notions of good taste with the belabored stroke of a pen. Advertisers complained, and there were occasional boycotts. But none of that prohibited him from becoming, at one point, one of the most visible cartoonists in America.

Wander around Northwest Portland and chances were you'd run into him, or he into you, as he blitzed up the sidewalk at speeds that rendered his electric-orange hair a tangerine blur.

And sometimes, he'd just barge in on you.

"I was teaching a class at Portland State University on cartooning," says animator Bill Plympton. "The class was almost over, I hear a bang, and here's this bulky wheelchair crashing through the door. This redheaded kid says, 'Are you Bill Plympton? Can you look at my cartoons?'

"His style was very crude and kind of amateurish, but yet it had a certain charm to it that I thought was pretty special. And when I started seeing his humor, then I realized this was something special. It was really dark humor, which is the kind of humor I like."

"Dark" is certainly one way to describe Callahan's humor. Many called him "politically incorrect," others simply "tasteless." But the cartoonist preferred another term—"survivor humor."

He'd survived plenty. Adopted at 6 months old by a blue-collar family from The Dalles, Callahan struggled with issues of abandonment and belonging, which he began medicating with alcohol as a preteen. (The fact, revealed late in life, that he'd been sexually abused by someone outside the family probably exacerbated his distress.) A car accident in California severed his spine in 1972. He was passed out in the passenger seat of a VW Beetle, driven by a guy he'd only met that night.

"Dexter had mistaken a Con Edison pole for an exit and had run straight into it at 90 miles an hour," he'd later write. "I didn't notice, though. I was too drunk."

Seven years later, he got sober, went back to school and reconnected with the artistic impulses of his youth. Despite having limited use of his hands, he taught himself how to draw by clutching a pen in one hand and dragging it across the paper with the other. He got published, got famous, offended everyone and far exceeded the public's expectations of someone left paralyzed before his life had even really started. At one point, his work appeared in more than 200 newspapers; in 1992, The New York Times did a profile with the headline "Defiantly Incorrect."

(John Callahan)
(John Callahan)

In other words, it was the stuff movies are made of.

That's something his manager, Deborah Levin, recognized almost from the moment she started representing Callahan in the late '80s.

"When I met him, and I flew up to Portland, he was such an engaging character," she says. "He had so much charisma, and he was so likable, and his story was so compelling. I said, 'This is great movie material.'"

But first, she encouraged him to write a book. He titled it after the caption on one of his more self-deprecating pieces, in which an Old West sheriff's posse comes across an abandoned wheelchair in the desert. "Don't worry," the sheriff says, "he won't get far on foot."

It ended up becoming a best-seller. But the goal from the beginning, according to Levin, was to persuade someone to take Callahan's life off the page and put it on the screen.

Someone eventually did. It just took almost 30 years to happen.

(John Callahan)
(John Callahan)

Gus Van Sant didn't know John Callahan well.

Although they ran in similar circles within the Portland arts scene of the '80s—Callahan was friends with street poet Walt Curtis, whose book Mala Noche inspired Van Sant's first film—the director has only vague memories of meeting him back then. He knew his cartoons, and thought they were funny. But Van Sant didn't even know Callahan had written a book, until his friend, Robin Williams, approached him with the idea of turning Callahan's autobiography into a movie.

"I didn't agree to it before I read the book. I was cautious," Van Sant says over the phone from Los Angeles. "But I thought it sounded like a good project."

Williams had discovered Callahan's cartoons in a San Francisco alt-weekly and became a vociferous fan—he'd later write the foreword to the cartoonist's second "quasi-memoir," Will the Real John Callahan Please Stand Up? At the time, Williams was in the midst of a career recalibration, and his Oscar-winning role in Van Sant's mainstream breakthrough, 1997's Good Will Hunting, had gone a long way toward legitimizing him as a serious actor. Naturally, Williams was eager to work with him again. And given Van Sant's history with films about irreverent Portland outsiders, it seemed like the perfect pairing.

(John Callahan)
(John Callahan)

Van Sant eventually signed on. Variety reported on the project in 1998 with the painted headline, "Van Sant goes good Williams hunting," and said Williams and his then-wife, Marsha Garces, were "actively developing" it for their company, Blue Wolf Productions.

At least two different screenplays were shopped around the next few years. But nothing ever came of them. Van Sant doesn't know why the film was never green-lighted—he suspects a movie about a brash, alcoholic, quadriplegic cartoonist just wouldn't fly with the kind of studios apt to make a Robin Williams feature at the time.

For Callahan, the delays were frustrating.

"We're all gonna be dead by the time this film is made," he told Van Sant.

He was two-thirds right.

(Jenna Biggs)
(Jenna Biggs)

The year after John Callahan died, Van Sant released his 14th film, the whimsical romantic drama Restless.

It didn't flop so much as quietly fizzle.

Critics described its plot, about a terminal cancer patient's love affair with a death-obsessed boy, as "twee enough to make your teeth ache." It was deemed "an almighty dud" by TimeOut London, while The Boston Globe declared it "torpidly precious." It disappeared from theaters without a trace.

It marked the start of a particularly fallow period in Van Sant's career—a prolonged stretch of commercial apathy and critical derision he'd never before experienced.

"Something kind of slid after Milk," says the critic Debruge, referring to Van Sant's Oscar-winning 2008 hit about slain gay rights activist Harvey Milk. "It's kind of impossible to speculate what that was. But you just look at his work and you realize he'd fallen into this weirdly sentimental treacle."

Following Restless, Van Sant released Promised Land, a drama about fracking in rural Pennsylvania. It fared better than its predecessor, but the praise was hardly full-throated—the consensus said it was "well-intentioned but oversimplified." With 2015's Sea of Trees, however, the reviews turned vitriolic. Starring Matthew McConaughey as a widower intent on killing himself in Japan's infamous "Suicide Forest," it was universally panned, derided as "dull," "maudlin" and "dramatically stillborn." When it screened at Cannes, the press openly jeered.

"If Gus Van Sant's filmography can be divided, Scorsese-style, into 'one for me, one for them,'" one critic tweeted, "Sea of Trees is one for nobody."

Asked to assess the past decade of his career, Van Sant told WW he put as much effort into those films as any of his others, and points out that he's absorbed critical drubbings before, going back to 1993's Even Cowgirls Get the Blues, the Tom Robbins adaptation widely regarded as his first major misstep.

"The interest that once greeted every new Gus Van Sant film has been evaporating for some years now," a critic for the Israeli paper Haaretz wrote in response to Sea of Trees. "And this latest movie, which can aptly be termed pathetic, only strengthens that feeling."

When news got out last year that a movie version of Don't Worry was finally heading into production, those who'd followed the project throughout its long, fraught journey knew better than to get their hopes up.

"When this announcement came out," says Tom Callahan, John's younger brother, "I immediately thought, 'We'll see. We've heard this before.'"

This time, it turned out to be legitimate.

Joaquin Phoenix as Callahan in “Don’t Worry, He Won’t Get Far on Foot”
Joaquin Phoenix as Callahan in “Don’t Worry, He Won’t Get Far on Foot”

Sometime after Williams' death in 2014, Van Sant was interested in revisiting the idea. So was Amazon Studios.

There was only one question: Who could play John now?

Williams had aged out of the role even before he died. Callahan had once said that, if the movie ever got made, he'd prefer Philip Seymour Hoffman to play him, but that wasn't an option, either. So Van Sant turned to Joaquin Phoenix, the actor whose career he helped launch with 1995's To Die For.

Phoenix hadn't heard of Callahan before being approached to portray him. But Van Sant didn't need an elaborate pitch to convince him to take the part—he just handed him a copy of the book.

"John is so funny and honest that you immediately see the power of his story and his journey and his transformation," Phoenix says during a brief phone conversation. "I don't think it required much more than that."

As he's known to do, Phoenix threw himself into the role. He watched tapes of interviews Van Sant had conducted with Callahan when he was still alive, and spent days at Rancho Los Amigos, the same L.A. rehab facility that treated Callahan after his accident, studying the mannerisms of other quadriplegics. He also came to Portland to hang out with, and ask questions of, Callahan's family and friends. In the end, the portrayal is not a precise impression, but it was never meant to be.

"We're not really close to the real Callahan," Van Sant says. "I was trying to show his story, and we weren't trying to do an impression of him."

In the film, Van Sant zeroes in on Callahan's battle for sobriety. While his time in Alcoholics Anonymous takes up only a small portion of his memoir, Van Sant saw it as the hinge on which the rest of his life swung—after all, his career as a cartoonist didn't start until after he got sober.

Joaquin Phoenix (left) as John Callahan and Jonah Hill in “Don’t Worry, He Won’t Get Far On Foot.”
Joaquin Phoenix (left) as John Callahan and Jonah Hill in “Don’t Worry, He Won’t Get Far On Foot.”

At points in the film, Van Sant gives in to his gooier tendencies. But unlike his past few movies, it never slips into treacle. It finds a mixture of sweetness and grit that feels like classic Gus Van Sant—or, at least, the closest we've gotten to it in a while.

The reviews have been generally positive. In his review for Variety, Debruge called it "a life-affirming sweet-and-sour concoction," while the Los Angeles Times described it as "flawed, intelligent and weirdly captivating." The New York Post praised Phoenix's performance, saying "he disappears completely into the cartoonist's off-kilter persona." He's getting early awards buzz, as is Jonah Hill, who brings a zenlike radiance to the role of Callahan's AA sponsor, Donnie.

It might not quite represent a full-on comeback for Van Sant, but it's at least a return to form—and a reason to anticipate what might come next.

(Thomas Cobb)
(Thomas Cobb)

"What's encouraging about this movie is it does find Gus Van Sant back in the mode his critics and fans have most responded to," Debruge says. "So whether or not the glory comes along with it, I don't think matters to him."

As for Callahan, both Phoenix and Van Sant are hopeful Don't Worry will reinvigorate public interest in his work. But even if it doesn't, for those who knew him, the film alone is something to celebrate.

"I don't have any illusions that this would be a huge commercial hit, because it's not about Superman or Black Panther," Tom Callahan says. "But the fact that it didn't completely die off, and the movie got done, is something in itself."