May 8, 2016 This article is more than 2 years old.

Making the connection is the difficult part—a long, vertical line of smoke and then twisting off into a new direction and across the atmosphere.

That’s how you draw letters in the sky with an airplane, and there are only five people on the planet skilled enough to make it their full-time job.

Greg Stinis learned how to pilot one of those planes before he learned how to drive a car. Not surprising for the son of a man who invented a new way to write sentences in the sky, whose plane hangs in a national museum.

“My dad would take my mom when she was pregnant with me, and that’s how it started,” he said. “I’ve always been in the air.”

Today, the 75-year-old still makes his living flying those curves and angles, leaving billowy white smoke trails that spell messages to people far below. Each letter is an optical illusion obstacle course. An ‘S’ looks like a straight line from the cockpit of his plane, and if the letters aren’t drawn at different altitudes—like on a staircase—his wingtips risk brushing against freshly placed smoke.

“I’ve been doing it for years and years and years, and still there’s a learning curve,” Stinis said. “You can’t see what you’re writing in the sky, everything is upside down and backwards.”

It’s his craft—a calling and his birthright. He was taught by his father, Andy. In turn, Greg is passing the skill down to his own son, Stephen.

Andy fundamentally changed the business in 1964, when he patented a new form of skywriting that allowed the family business to grow exponentially. It takes more than two minutes and a great deal of skill to draw a single letter with a single aircraft, so Andy invented skytyping, which involves five planes flying in steady formation, and a computer system programmed to belch smoke puffs, to create letters in under four seconds.

Here’s an animation of his patent drawing showing how the process works:

Each letter stands as tall as the Empire State Building and each message stretches five miles across. In 1979, the family started Skytypers Inc. Today, Greg and Stephen, 41, own and run the business.

The family now finds itself staring down another moment of change, this one ushered by new technologies that promise to reshape the next generation of skytyping—potentially at the cost of the art of single-plane skywriting. That will be a weighty decision for the youngest Stinis.

Most of the jobs they do are with the skytyping method, and most of those are commissioned by businesses looking for ostentatious advertising high above World Series baseball games, sprawling music festivals and NASCAR races.

Occasionally, someone will request single-plane skywriting. That’s Greg’s specialty, the craft in its truest form. He always starts by pulling out a little notecard and sketching the message, annotating his arches, his twists and the exact number of seconds he’ll need to release smoke to draw each line of each letter.

“I like the challenge of what I do and the fact that it is something that’s an art piece,” he said. “It’s like playing the piano, once you learn a certain tune a certain way.”

They can relate that there’s a real live person up there, doing artwork in the sky.

But if the sky is his palette, the wind is a devilish foil. Skywriting can be a fickle art. There are no do-overs, no erasing or re-drawing—only a race against time.

Sometimes he starts traffic jams. People will stop their cars to stare into the sky, pointing their fingers as his airplane tumbles around and around. Great puffs of white smoke emerge, sit for a moment, then begin a lazy float across the atmosphere.

“They can relate that there’s a real live person up there, doing artwork in the sky,” he said. “The only bad part is that I can’t take my canvas of art away with me. Eventually it fades away. It goes with the breeze.”

He never sees his finished work as it’s intended for people on the ground. It’s not until he lands his plane and scours social media for photos that he truly has a sense of his smoke, or validation.

Stinis wants to take sky messages to the next level, further distinguishing the medium by adding vivid colors to the smoke. That’s easier said than done. His company has been trying to make reliable colored smoke for more than 40 years, but the dyes have never cooperated with propeller planes. The chemicals would leave multi-colored streaks down the sides of the aircrafts, and cleaning them cost too much to justify keeping the service. Greg said he’s working with a firm in Europe that is very close to creating a dye that will work.

Take a 360° ride with the skytypers. (Best if experienced on mobile).

The first time anyone saw sky writing was in 1910, when British Royal Air Force Major John Savage developed it as an alternative means of communication. Another officer later capitalized on sky writing by spelling out the name “DAILY MAIL,” above Epsom Downs racetrack in England. It arrived in the US in 1922, when captain Allen Cameron flew above New York City, spelling out “HELLO USA.”

In 1932, Greg’s father started writing “PEPSI,” in the sky for the Pepsi-Cola company, which liked the response so much they offered Andy Stinis a contract. They helped him obtain 18 more planes and asked him to spread the word across the nation’s skies.

Today his father’s main plane, a red, white and blue Travel Air D4D “Pepsi Skywriter,” hangs in the Smithsonian National Air and Space Museum in Washington DC.

With so few people operating in such a rarefied business, Greg and Stephen Stinis command impressive global market share and frequently travel abroad for work. Stephen flew to Spain in February to get approval to establish a fleet of six planes there, and they own fleets in South Africa and France, as well. Greg has flown up and down the coast of Japan leaving messages for Dentsu, the largest Japanese advertising agency. On Father’s Day in June 2015, the skytypers were commissioned to work in Dubai, where they buzzed over Sheikh Mohammed bin Rashid Al Maktoum and his wife during a yacht party, writing out the pair’s initials inside an oversized heart.

“I go wherever the business goes,” Greg said.

The requests can get funky, too. Some people have asked to put curse words in the sky (they are refused). At least one person, looking to break the world record for the largest drawn penis, was also turned away. During the 2016 Rose Parade—for an undisclosed but large sum of money—five sky typing planes wrote “TRUMP IS DISGUSTING” over Pasadena, California, a reference to the polarizing Republican presidential hopeful.

“We’re not proud of it,” Greg said, the regret in his voice palpable. “We didn’t like it. We didn’t want it.”

And the company won’t be doing it again, he said. Best to keep the messy world of political mudslinging down on the ground.

For years, the Stinis family zealously guarded their patents and the sole authority to book their own jobs. Several people approach them each year eager to learn the craft, but aside from one man in France, Greg said he turns them away. His son, Stephen, has yet to complete his own training. It’s a family business and Greg intends to protect it.

“It sounds selfish I guess, but when you have a unique business you like to keep it that way,” he said. “If I trained ten other people to do exactly what I do and they stayed in Los Angeles, well, I’d lose all the jobs.”

That means the future of the business, once he’s gone, will fall almost entirely to his son, who has no children of his own.

Stephen may have the same cadence as his father, but the pace at which he approaches his fortune is markedly different. He eagerly chats about incorporating computer tablets and social media campaigns into sky messaging. More technologist than artist, he’s more likely brainstorming ways to produce custom logos in the sky, or glow-in-the-dark smoke, than the subtleties of old-fashioned skywriting.

His respect for the craft of single-plane skywriting is evident, but he questions its efficiencies in a world where people are more connected and distracted than ever.

“With our society becoming more ADHD, it’s difficult with the skywriting because it takes about two-and-a-half minutes to form a letter,” Stephen said.

Art in the sky is about to meet a fork in the road.

“I can look at it and say: It’s a dying art form, it died with my father—or I’ll take the torch and run with it,” he said.

He paused, sinking into the gravity of his inheritance.

As it turns out, the answer may be tucked inside a little box Stephen has kept for years. It’s where he keeps all those little notecard sketches his father draws before rumbling off into the sky to write a message. When his dad finishes, he usually heads back into the airport hangar, peeling away his gear and discarding the cards.

Stephen often follows, quietly scooping them up and depositing them away—the secrets of the art, and the one permanent representation of his father’s work.

“Sometimes I try to collect them, and that’s for my own personal use,” he said. “For understanding later in life the schematics of how to do these letters.”

Making the connection is the difficult part, including the handoff from one generation to the next.

The form has staying power, in spite of its fleeting nature. Every note the Stinis family writes—written by one plane or five—captures the attention of thousands, whether it’s advertising for a potato chip company or a proposal of marriage.

“The fact that millions of people see what I do—I can do some unique things with it,” Greg said. “Quite honestly, I’ve married off thousands and thousands of people. I’ve changed their lives.”

When Greg Stinis tells the tales of his message-making, each one seems increasingly outlandish: the great traffic jams and the World Series outfielders who missed catches to stop and read his messages. But every story shares one distinguishing thread, they all end with people stopping their routines to look into the sky. They stop to look at his airplane, with a person inside, sending smoke signals of a different sort for people to read thousands of feet below.