What It’s Like Taking Photos of the Ultra Wealthy from Inside a Helicopter

Jeff Cully has a unique window into an exclusive world of obscene wealth, marauding development, and breathtaking beauty. He’s been hanging out of helicopters as an aerial photographer for nearly three decades. Now, shooting primarily over the Hamptons, Cully enjoys the view while he gets paid to capture the sprawling summer playgrounds of billionaires and celebrities.

Cully got his start working as an assistant for acclaimed photographer Thomas Kelly. “I had just turned 19 and was in the back of an army helicopter—a French Alouette that probably should have been mothballed decades earlier—with the big bay doors off, cruising over Kathmandu. That hooked me,” he said.

VICE talked to him about the close calls, eccentric clients, and why even the most intimidating rollercoaster has nothing on a helicopter.

VICE: How do you end up an aerial photographer in the Hamptons?
Jeff Cully: I had done summer sessions [in photography] at the Rochester Institute of Technology starting in eighth grade. It’s all I’ve ever wanted to do. I ended up overseas for a few years after high school—I went to South Asia and the Middle East. Then San Francisco, East Village… and then moved out to the beach. I summered there growing up and always had wanted to live there. Plus, it’s a rather beautiful area both photographically and to live in. The money is great in season but it’s much more about the area itself than the money.

Who hires you?
In recent years, I was flying three to four times a week—[working for] real estate, advertising, film work, custom builders, home owners, the news (ABC, NBC, CNN, Bloomberg TV, Business Insider, NYT). People love aerial views/footage. The Hamptons are always a hot item in the summer.

How does a typical shoot go?
You plot your route, double-check the night before, go over the route with the pilot on the laptop before you even get in, preflight the helicopter with the pilot. Load in your gear, take the door off, strap in, and hope the weather stays good.

Most aerial photogs get a list of locations, fly them, shoot/film them and that’s it. I take my lists and then add everything/anything in between the assigned locations and never stop shooting or filming during the flights. That led to being known as the “Hamptons stock” guy for news outlets, magazines, TV, etc. I have a 63TB collection of “all things Hamptons” that many have drawn from over many years.

What’s it like?
Trust in thy seatbelt is the motto. You’re strapped in a seat and leaning almost completely out with the camera in your hand. Occasionally you’re sitting on the floor with no seat, feet on the skids. It’s sensory overload. Even as you’re filming, you’re watching the gauges, you’re looking for places to land, just in case. I’ve been flying with the same guys for over 20 years—they’re agricultural aviation guys. The communication [with your pilot] is critical. The coordination of the movement is almost like a ballet.

What are some memorable residences you’ve photographed?
There’s a lot of excess out here. [Industrialist and junk bond king] Ira Rennert’s Fair Field Estate in Sagaponack, NY. This place is nuts. It was America’s biggest residential compound—it’s sprawling and ridiculous. Multiple pools, gardens that go on and on, multiple tennis courts side-by-side. It’s completely over-the-top. Though his gardens create some really cool patterns so it photographs beautifully.

And David Tepper—he tore down the house because he didn’t like the view of the sunrise or something. He wanted to rotate the angle of the house about a degree and a half from what was there before. I caught Tepper and his girlfriend on the upper deck of his house a couple of times. The man probably hates me, but that’s OK. Yep, that’s me again, coming over your house, running circles around it at 8 in the morning with that whup-whup-whup. If you look down at his compound, his pool looks like a penis with two giant balls. You get a mix—from the extremely eccentric to wealthy people who are extremely normal. It’s the full range. Any client that puts me in the air, I’m pretty happy with.

Any weird occurrences?
One time I saw smoke, so we diverted and headed towards it. It was like this gazillion square foot house on fire. We were there before the fire department. We stayed up top and went around and around. They were some incredible pictures of this (relatively new) monstrosity of a mansion burning down.

I was working on this campaign for Hustler Powerboats, these million dollar plus, 50-foot race boats that go incredibly fast. We were filming this brand new model out on the ocean, probably five or six feet off the deck—right over this boat. And we blew the primary hydraulic system. What we realized when we got back, was that we coated the boat from bow to stern (and the owner and his wife and best friends) with hydraulic fluid. Things like that happen!

Any close calls?
Yeah. It’s an occupational hazard. We refer to them as “in-flight incidents.” It’s not a lot of fun. In tight turns—downdrafts, crosswinds, mechanical failures—you get those oh dear god moments. Even as the photographer, you’re always looking around for a place to land if everything goes to hell. Auto rotation is an interesting experience—that when you lose all power. So you point the stick all the way forward, drop the nose so you’re going straight towards the ground, building up enough power in the rotors. At the very last minute, you jack the stick back, release the transmission, and (hopefully) land softly. That’s not something I would wish on anyone.

What was your weirdest assignment?
The first time Anthony Weiner screwed up—I don’t normally do paparazzi stuff—but what that shot would have been worth if we’d got him out on the deck or something. We went from location to location around the Hamptons, and ended up buzzing around Jon Stewart’s house in Sag Harbor, where he was supposedly staying. We went searching for Weiner, but we got nothing.

How expensive are your shoots?
More photographers like working from [fixed wing] planes. It’s safer, it’s slower and it’s a quarter of the price. But I consider planes a pain in the butt. It takes a lot longer and you’re limited to your angles. A helicopter is high energy, but it’s not cheap. If you take up an R66, you’re looking at $1,200-$1,800 an hour, just for the airframe. No peanuts or drink service, obviously. You can easily spend $30,000-$40,000 a year on helicopter rentals, on the low end.

Drones are increasingly used for aerial footage now. What’s lost?
At some point, they’ll probably be able to emulate the movement of a handheld in a helicopter, but right now—you can almost always tell its drone footage. Between a good pilot and what I can do with a handheld camera—you just can’t get that with the drone.

What traits do you need to be a great aerial photographer?
You need a really good eye. Gotta be able to multitask on a level most people couldn’t dream of. You gotta know the equipment. Situational awareness. And you better be a pretty damn good photographer. You have to be willing to get into a helicopter. They don’t glide—they drop like stones. I’d never take a girlfriend or significant other up in a helicopter with me—never have, never will. Not going to put both of us in that situation at the same time.

Interview has been edited and condensed.

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