In the opening scene of The Land, an unseen guidance counselor lays out possible futures for the film’s four high school protagonists. It’s lives as mechanics and welders, blue-collar jobs that once promised entrance into a thriving middle class that no longer exists. With dreams of escaping the urban decay of Cleveland as sponsored skateboarders, the boys instead chose a less legal path. And anyone familiar with the “at-risk youth” movies of the 1990s – from Boyz n the Hood and Menace II Society to Kids, Hurricane Streets, Juice, and Straight Out of Brooklyn – knows that path doesn’t end well.

Cinematographer Steve Holleran spoke to Filmmaker about the making of The Land, including his month-long Cleveland scouting trip, shooting a Dragon from a speeding skateboard, and what to do when one of your primary locations burns down.

Filmmaker: You met The Land’s director, Steven Caple Jr., when you were both students at USC. Were there particular films or filmmakers you bonded over?

Holleran: The first time we worked together was on a class project where we had to recreate a scene from Serpico. We liked those kinds of movies and we liked gritty indie things like Chop Shop, which was a big favorite that we bonded over. I just think we have similar outlooks on the world and similar tastes.

Filmmaker: I’m trying to envision this college Serpico exercise and I’m picturing the scene in Rushmore where Jason Schwartzman’s character stages his Serpico play.

Holleran: (laughs) Yeah, Steven was holding the boom and recording sound for me and I had the camera. We had a young actor with us that I’d cast and we were on the roof of some warehouse on the east side of the 110 in the South Central area (of Los Angeles). I had another couple friends come by to help out for a little bit, but Steven was the only one who stayed the whole time. I didn’t forget that. So when Steven had to do his scene, I shot it for him. And then every time he had something else to direct, I’d shoot it for him. We made all kinds of things, just passion projects together, but The Land was the first job we ever did together where we actually got paid anything.

Filmmaker: The Land began life as a short. Did you shoot it as a self-contained piece to send to festivals or was the intention to have it be a demo you could show to raise funds for the feature?

Holleran: Steven was already in the process of writing the feature version, but he also had written a short version for a screenwriting class at USC based off of some kids he’d met in LA that were dealing drugs to fund their skateboarding passions. I don’t think necessarily at the time we saw it as a way to gain funding, even though it was integral in that process later on. It was more about us wanting to step up and do something visually on another level than we had in the past. We shot it over one weekend in Los Angeles and I think we had maybe a thousand dollars or $1,500 in the budget. I just called all my friends with gear – a guy came with a Red, a Steadicam guy showed up – and we ran around town all day and all night for a few days and just picked off all these little moments, which were basically a day in the life of these four kids that you see in The Land.

Filmmaker: Tell me about this extended scouting trip you and Steven took to Cleveland, where he is from. That’s an incredible luxury for a low-budget film, to get to spend a month immersing yourself in the environment.

Holleran: We spent three or four weeks running around different parts of the city finding locations that spoke to the story. I wanted to hand pick each place for the texture, for the color, for the layout, for the light, for all of those things. I’d never had the chance to spend that much time location scouting just with the director. Usually it’s two days before the shoot and everyone is in the car and you’re basically doing a tech scout for a place that you already know is probably going to be the location.

We flew out to Cleveland in April and we stayed at his fiancé’s cousin’s house. They gave us an extra bedroom, so I was on a little twin bed and Steven was on a little blow-up mattress on the floor. I had butterfly sheets. It was great. They took really good care of us. His fiancé’s cousin’s boyfriend, who was a cop, lent us his civilian car. It was like this low-rider with tinted windows and we drove that around town and went everywhere. We explored abandoned warehouses, underground subways. We went to rough parts of town at three in the morning on a Friday night so we could see the dealers and the prostitutes at the Marathon gas station. Steven toured me around his old school, all the houses he grew up in, where he got in his first fight. I took thousands of photos on my phone and compiled them all into this Google drive document. We ID’d a good 85 percent of the locations before production even got there.

Filmmaker: I read that the original location you chose for the hot dog shop burned down before production. It’s a pivotal location – the lead character Cisco (Jorge Lendeborg Jr.) lives above it and his uncle (Kim Coates) runs the place.

Holleran: Two weeks before we went out to start (principal photography) Steven called me and told me the hot dog spot burned down from a grease fire. Steven was so sad. One of his favorite locations was gone. We went to a bunch of different hot dog places when we were scouting looking for the right one and I think we sampled a hot dog in every spot. Old Fashion Hot Dogs was Steven’s favorite hot dog of all the ones we tried so I think deep down maybe that’s why we picked it as our back-up. (laughs) I really liked that space that we used. It had this long counter with all these red seats. It was so narrow you could barely fit a crew in there. I just loved the claustrophobic feeling. It felt like if I lived there, I would want to get out too.

Filmmaker: And you had around 21 or 22 days to shoot?

Holleran: At this point I can’t remember, but I think officially it was 21 days. Then we shot another six days off the books. We called them “Black Op Days” or “Phantom Days.” On those days I would take my camera crew and Steven, and sometimes hair and wardrobe and make-up and the actors, and we just cruised around in a van shooting extra scenes. I’d say a good third of the movie we shot off-schedule because (production) wasn’t going to give us any more time. So we just shot them ourselves. Then I shot another eight to ten days of B-roll footage. I’d just drive around town with the Red Dragon and the anamorphics and at magic hour I’d post up under a bridge and shoot a really pretty shot that we needed.

Filmmaker: There’s two extended slow-motion sequences of the boys skating together. Did you shoot those on “Black Op Days?”

Holleran: Mostly. We shot the street montage totally on an off day. I just had my Sector 9 skateboard and the Dragon. I put it in slow-mo mode and I had my first AC (Dennis Scully) with me pulling focus. We would skate around and see a street we liked and just shoot. When Steven started writing the script for The Land and he told me it was going to be about skateboarding, I was so excited because I grew up surfing and skateboarding and I had an intimate connection to board riding.

Filmmaker: Tell me about the decision to shoot those skateboarding scenes in slow motion.

Holleran: It’s their escape. It gives them a sense of euphoria that they don’t have in the rest of their life, this feeling of flying and freedom. We wanted to capture that feeling with the visuals. I would skate with the boys with the camera and that in itself was a big experiment. I’d never actually skateboarded with a camera as big as the Dragon before, but with the help of Panavision and my AC we rigged it out in a way that allowed me to hold it with two hands on the top handle like a sub-machine gun. I could get going pretty fast and then insert the camera into their world so that the audience could also feel that sense of freedom.

Filmmaker: Did you ever eat it on the skateboard?

Holleran: I did, yeah. Once. I ate it in the Max Hayes High School hallway, that dark hallway where we shot the second skate montage. We were shooting and it was looking ugly and I couldn’t figure out what to do about it. This was on one of our “Phantom Days,” so I didn’t have any lights. So I thought, “I’ll turn the (practical lights) off because there’s this big window down at the end of the hallway and then I can shoot them as silhouettes.” So I turned the lights off and it turned into one of my favorite scenes. It looked so cool, but it meant that I couldn’t see the ground when I was skating. We were really into it so the boys were ripping down the hallway. Toward the end of the day I’m chasing after them, probably doing 15 miles an hour, and I hit a nice big chunk of glass on the ground on my left front tire and I just flew. Luckily my AC had left the dovetail plate on the bottom of the camera, which is this big piece of metal that allows you to clip into and out of tripods and other things, so I was able to lay the camera on the ground and let it skid and then I just ate it super hard. That was the only bad wipeout I took. I think a wipe out on the asphalt outside on the street would’ve been the end of me.

Filmmaker: There’s a shot during that first skate montage where one of the actors does a kick flip and the camera does a 360 as the board is spinning. Was that one of your iPhone shots?

Holleran: That was actually with the Dragon. For something like that you’d love to have some 360 remote head on a crane, but we couldn’t afford one or probably even get one into the warehouse where we shot that. So I called my gaffer (Gregory Doi) and I told him that I wanted to do this 360 rotating shot that Steven was in love with. Greg is a welder and he welded me this four-pronged apparatus where you’d mount the camera in between the prongs. We connected that rig to a camera cart and I sat on top of this camera cart straddling it and Greg pushed me behind the skateboarder as he did his kick flip. I basically had to spin the camera once really fast and then catch it in a perfectly horizontal position, which was not easy. (laughs)

Filmmaker: How many takes did you need?

Holleran: I think I did 20 takes. I got it a couple of times, but the one in the movie is the best one. So that’s how we pulled that off. It cost us all of $30 for the metal.

Filmmaker: In that same space there’s a pretty incredible stunt where a character leaps over a wide gap in one of the warehouse’s floors. One of the camera angles is from the floor below looking up, so it’s obviously not a cheat.

Holleran: We got a stunt skater who could actually clear that hole. He tested it on the street – we measured out the distance and it’s a huge gap. It’s like a ten-foot gap and it’s a twenty-foot drop to the floor below, which was covered in bricks and glass. We shot a bunch of other angles of him actually doing the jump with netting down there so if he fell on his first couple of tries he’d be safe. He kept making it and making it and he said, “I want to do one without the net.” So we shot one on the iPhone without the net from below. He probably cleared it twenty times.

Filmmaker: The iPhone doubles as a prop that the character of Junior (Moises Arias) picks up during one of the group’s carjackings. Did the actors actually operate that camera? And are those anamorphic flares I see on the iPhone footage?

Holleran: Yeah. Moondog Labs makes an anamorphic adapter for the iPhone 6. I reached out to them, they sent me one and we gave it to the actors. We thought maybe it would give us some unique, naturalistic material of the boys interacting together. We talked about using a GoPro or a DSLR, but I wanted it to feel like a phone so we just used an iPhone. Moises was always operating it and I swear he’s going to be a director some day. He’s got a good eye and he knows when to move the camera and he kept getting really cool stuff.

Filmmaker: There’s a moment late in the film where Cisco makes a decision to escalate the severity of his criminal activities – and that moment unfolds in a four-minute tracking shot. Walk me through the difficulties of pulling that shot off. It’s a huge area to have to light at night.

Holleran: It was tough. We only had one crane that night and we didn’t have big enough lights to really light that scene the way I wanted to. We also lost the house we were going to use, which was close to the street, and we had to redesign the shot and send (Cisco) deeper into this wooded section in order to get to a house that we had a permit for. And then we had lightning strikes that night and they got within a five-mile radius of the genny, so we had to shut down for three hours.

We were really pressed for time, but we felt like we needed to do that as a oner because we had established this aesthetic where every time Cisco goes into what we called “business mode,” we wanted to track with him. We choreographed it over a number of hours and we lit all the different sections and set up all our light gags, like for the passing car taillights and the gunshot flicker effects. I think we ended up using the first take, though. Our Steadicam guy Ivan Valadez just nailed it. That was a tough one, because he had to walk down this grassy hill and track through trees and it was really dark.

Filmmaker: That’s incredible to get that shot on the first take because you’ve got all these moving parts –whoever did the light gag for the tail lights has to haul ass out of the way before the camera pans around and then you’ve probably got a little entourage with the director and the sound guy and maybe an AC traveling behind the camera.

Holleran: Yeah, there are tons of moving parts. We had all the production crew and the trucks stuffed down a side street so you couldn’t see them. Then we hid the crane with branches and trees so you didn’t see the base of it in the shot because it’s hanging a moonlight backlight for Cisco. And then a bunch of us are walking behind our Steadicam guy Ivan – a grip, the director, a focus puller, sound. We’re all there trying to stay out of the frame.

Matt Mulcahey writes about film on his blog  Deep Fried Movies.