Leap of faith 

Behind the scenes of Freeload, a documentary about modern train hoppers

It was 1 a.m. in Toledo, Ohio, on the morning of his 29th birthday, when Daniel Skaggs plummeted 25 feet from a train trestle into the Maumee River. He and his fellow traveler, Skrappe, had been trying to hop a FedEx train to Chicago. "We were running next to the train," Skaggs says. "I was in the front. We started to cross over this trestle and all of a sudden the bridge is gone—there's just a hole in it—and I'm falling."

Besides his sleeping bag and clothes, Skaggs, aka "Skeeter," had 30-plus pounds of camera equipment on him, the weight of which immediately sunk him. "It didn't really hit me until I hit the water what had happened," Skaggs says. "But all of a sudden I'm sinking to the bottom of the river with my pack on, and I'm struggling because I can't get it off. I was drowning. I finally worked my right arm out of my pack. My main thing was getting to the surface because I had no more air in my lungs. At the same time I'm like, 'I gotta get my pack. Otherwise everything is fucked.'"

When he surfaced, Skaggs recalls Skrappe whispering loudly, "Skeeter! Skeeter!" from the river bank, trying to keep them from being spotted by the nearby drawbridge operator and the train policeman, aka "the bull," who was already shining his flashlight near the river's shore. "Hey motherfucker," Skrappe whispered again. "Are you alive?"

Skaggs' shoulder and ribs felt battered. "I ain't good, man," he recalls telling Skrappe. "I can climb up the bank, but I need you to carry my pack." Skrappe grabbed the waterlogged pack full of Go-Pro cameras and mics and an Olympus tape recorder. They crawled back up the bank, away from view, and walked back to the train yard.

"I was soaking wet," Skaggs says. "And even though it was June 21, I was freezing and in shock. Just then, a train pulled up and we climbed on. And within five minutes we were on our way to Chicago."

Not many documentary filmmakers immerse themselves so deep in their subject matter that they end up falling through bridges in the middle of the night. But Freeload, a new film by Skaggs and Highway Goat Productions about contemporary train hoppers, required a hands-on approach in order to capture a culture that travels thousands of miles in just days at a time. More specifically, it required Skaggs to uproot his life in Missoula and spend 18 months riding the rails to shoot the film.

If the final cut of the documentary is any indication, the behind-the-scenes challenges weren't for nothing. Freeload, which screens at the Big Sky Documentary Film Festival Feb. 21, follows a handful of young travelers—anarchist punks, couples in love, brothers—through 42 states as they hitch rides on the rails, sleep in dilapidated buildings and beg for change. It's not a documentary about train hopping so much as it's an intimate portrait of a few particular kids—including Skrappe and his brother Xmas—who have chosen to reject a mainstream path for windy boxcars and dirty sleeping bags.

Skaggs came up with the idea for Freeload several years ago after his own history with train hopping. "I got interested in riding trains because I had been hitchhiking and I found out about this group of people who were riding trains in the 21st century," he says. "I became obsessed with freight trains—with the culture, with the patches and the memorabilia and the rail enthusiasts. Everything about it."

click to enlarge Xmas shows off a bottle of trinkets he’s collected while hopping trains.
  • Xmas shows off a bottle of trinkets he’s collected while hopping trains.

He says he also felt like the culture got a bad rap and he wanted to change that viewpoint.

"There is a stigma associated with this group of people that maybe they're scary and dirty ... but the people I know that ride trains are just like people we all know," he says. "They come from all different backgrounds, they have brothers and sisters and moms and dads and they have the same emotions that we do as basic humans. So with that, the story of Freeload came about to speak on these things."

In 2010, Skaggs met University of Montana media arts students Ryan Seitz and Mather McKallor. They were all working at the Good Food Store in Missoula at the time, and Skaggs, a UM graduate, was also working as an organic vegetable farmer. Together, they started turning Freeload into a full-fledged project. They tapped another GFS coworker, noise musician Bryan Ramirez, to create a soundtrack.

"We went all in," Seitz says. "Mather and I are big documentary film enthusiasts—Les Blank, the Maisel brothers, Allan King. I admire those filmmakers because they do direct cinema or cinéma vérité, letting the story unfold on its own. That's what we wanted to do."

They put together a crew, including producer Neil LaRubbio, and after successful campaigns with Kickstarter and Indiegogo, plus a backyard pig roast fundraiser, they started filming.

That's where the project got tricky.

For a while, Skaggs and another camera operator approached groups of train hoppers and followed them from town to town while Seitz and McKallor tailed them in a car so that they could meet up and collect the footage for editing. That lasted about three months until the logistics fell apart.

"We decided it just wasn't feasible to do it that way because if I needed to ... go 2,000 miles away, these guys can't follow me," Skaggs says.

The Highway Goat crew went to Seattle and set up shop, leaving Skaggs to gather all the equipment and set out on his own. He mailed footage back to Seattle as he filmed and kept traveling across the country.

"In California we all said our goodbyes and I was basically at the fate of the characters of Freeload for the next 15 months," he says. "With [all the camera equipment in tow] it was the craziest type of traveling I'd ever done."

Though Skaggs wasn't new to train hopping, his filmmaking skills were amateur at best. Seitz says they had to review the footage and give Skaggs tips on how to make his shots better. The film shows the result: striking footage of oddball characters and boxcar-view landscapes."It was a crash course in filmmaking," Seitz says. "He was camera man and sound dude all by himself."

Besides falling into the Maumee River, which happened toward the end of production, there were a couple other near disasters. In Portland, Ore., just two weeks into meeting and hanging out with Skrappe's group of travelers, Skaggs got drunk and stole beer from a convenience store and brought it back to the train yard. The cops showed up to haul him off to jail and he found himself in a predicament: take his camera equipment to the jail where it might get lost, accidentally or otherwise, or leave it with his newfound companions? He decided on the latter. After being released six hours later, he nervously wandered through the city trying to track down Skrappe and the gang. He finally found them in the parking lot of a Fred Meyer.

"There were 10 train-riding kids sitting outside with their packs yelling at people and causing a ruckus," Skaggs says. "And Skrappe, who is such a charismatic individual, comes running up [with] my pack. He was so proud that he had [kept it safe]. And we eventually formed a really strong bond."

It's easy to come to Freeload with some skepticism and annoyance. The kids who pass through Missoula in their brown, patchwork clothing and piercings, who travel in raucous packs with tag-along dogs—they're not often welcomed even by those who embrace alternative lifestyles. And while Freeload doesn't mask the more obnoxious aspects of the culture, it does humanize its characters in surprising and touching ways. Blackbird, for instance, goes to visit his grandmother, who sweetly packages up toothpaste and other essentials for his next journey. She knows she can't change his mind about hopping trains, so she can either sever their relationship or choose to support him anyway.

click to enlarge Ponyboy points out a tattoo of a railroad track.
  • Ponyboy points out a tattoo of a railroad track.

Another scene shows Ponyboy philosophizing with his dad, resulting in some self-reflection about how the "freedom" of train hopping isn't always what it's cracked up to be. His dad, for his part, admits he's a little jealous of Ponyboy's lifestyle. In the end, the film gives the train hoppers a chance to pause and think about why they do what they do. It also gives viewers a chance to think about their own prejudices.

"The word hobo is such an iconic word," Skaggs says. "It's associated with American storytelling and it's this giant slice of American history—people with sticks and bindles traveling across the countryside through cities. The sense of freedom of riding trains and traveling is very gripping. It's exciting. But on the other hand it's scary and lonely, so you can imagine the confusing complexity of those emotions."

For Skaggs—and his crew, who came to know the characters during the editing process—it was a life-changing project. They spent their savings on making the film. Several months into the production, Skaggs found himself wandering around with holes in his shoes and no money to replace them—until a railroad worker named Bob offered up the pair he was wearing.

"It was difficult after a year of being in the trenches, living on the street with these people when I knew I didn't really have to," Skaggs says. "And there were a few times when I really didn't want to do it anymore. I had come from graduating at the top of my class at the university, getting an award and operating my own farm, to putting myself out there on the street being judged every day by the populace. But it opened my eyes to so many things. For every shithead out there, there is a kind-hearted person. Yeah, there's a lot of bad people and I saw some of that, too. But I saw more good than bad. Seeing the kindness that still exists with the human race in America, I can't stress enough how great that was."

Freeload screens at the Wilma Theatre Fri., Feb. 21, at 7 PM during the Big Sky Documentary Film Festival, which opens Sat., Feb. 15. Check out next week's Indy for full festival coverage.

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