Is this man the most talented creative in America?

In 2011, while looking to make some money, he decided to submit an idea to Victors & Spoils, an agency that was working with Harley-Davidson in a new experiment with crowdsourcing ads.

Hiler’s idea was “No Cages,” a television spot where people and things were stuck in huge cages. It promoted the bike brand’s customization program, which, essentially, freed you from these metaphorical cages.

Hiler — otherwise unemployed at the time — saw his ad get made. Thrilled with the experience, he approached his wife, who happened to work at Cornett Integrated Marketing, in Lexington, Kentucky, and told her that he wanted to “make ideas.” Christy Hiler, chief strategy officer at the agency, told him to come work for her. Initially, though, she struggled with finding a way to put his weirdness to work. “To be honest,” she said, “we sometimes still don’t know how to use him.”

The struggle has paid off: Hiler has since been behind of the more interesting and ridiculous campaigns in a generation, including “The World’s Longest Hashtag,” created to promote A&W’s new chicken sandwich (#supertastylargeandinchargetexastoasttwohand-wichmadewithdeliciousonehundredpercentwhitemeathandbreadedchickentendersandyourchoiceofclassicorspicypapasauceeitherwayyoucan’tgowrongwowthatsoundsgoodyouneedtotryoneit’sonlyavailableforalimitedtimeI’mgoingtohavetogogetonemyselfareyoustillreadingthisseeyouatAandW)

He has won a Webby Award for “Beardvertising” — ads that clipped onto people’s beards — and worked on Applebee’s “Girls Night Out” push that featured perhaps the most annoying spokeswoman of all time.

Creative advertising may be Hiler’s second love after Christy, but Kentucky is a close third. That love for Kentucky — “There isn’t as much hype about Kentucky as some places but it’s really cool” — inspired Hiler, along with a friend, to start what might be his most well-known business: Kentucky for Kentucky. It began in 2011 as a crazy idea to crowdfund a Super Bowl commercial for the state, but since then, the brand has turned into a retail company that’s actually profitable.

“We collaborate with the cool creatives here and make products that represent this state,” said Hiler. Products include a sweatshirt that says “Y’all” ($50), “Kentucky Kicks Ass” bowls ($30) and various map prints. (The company’s initial slogan, “Kentucky Kicks Ass,” was so big that GE used it at the Savannah College of Art and Design to attract hires to the company’s office in Kentucky.)

“While Kentucky might not be viewed as a big creative hub, I think it’s definitely starting making some strong moves to achieve that status,” he said. “We’ve got some really cool startups coming out of Kentucky. We’ve got a lot of great agencies in Kentucky doing some really great work. We’ve got a lot of really creative entrepreneurs shaking things up.”

‘Prolific and perverse’
“Whit’s mind is prolific and perverse. I mean perverse in a great way: His ideas often challenge what is normal and expected,” said Griffin Van Meter, Hiler’s business partner in Kentucky for Kentucky. “He’s a Duchamp, a real artist. His ideas are over the top, but he’s creating a new top. He’s not worried about what people will think; if anything he’s getting them to think. Or maybe just he’s trying to get people to laugh.”

But two jobs — agency guy and entrepreneur — aren’t enough for Hiler. He also happens to be behind some of the biggest non-client-mandated “work” in recent years. You’d be hard-pressed to call some of it advertising, but it certainly is creative. A few years ago, Hiler attempted to make a splash on the Internet by posting and distributing fliers inviting people to recreate a scene from “The Human Centipede.”  Those ended up on the front page of reddit and in blogs everywhere. In another stunt, Hiler hosted a series of meetups that offered to teach people how to masturbate. Another was Rainbow Bus Club — a meetup for straight men to go and be gay “for an hour or so.”

“Making people uncomfortable is just something I’m good at,” said Hiler. “If I get my dad super uncomfortable, it’s a good idea.”

Hiler’s career path is meandering. By his own admission, he got into advertising late. The Lexington native might not have looked like he was destined for greatness after high school (he “barely passed”). He took off for Colorado to go to a community college called the Colorado Mountain College while working at the ski resort and a local eatery. Then, at 22, he found himself with a DUI. It was time to leave Colorado. “I was having too much fun.”

He came back home and began to work at a car dealership as an “Internet Sales Manager,” a quirky job title from the Web’s early days. “I was just good at sales. Sales are easy. Your results are clear. Every month, you sell X number of cars,” he said. “I was really good at selling cars.”

But an itch had been building within him, and after eight years of selling cars, it was time to scratch it. Hiler set out to start his own clothing company, Attus Apparel. As with most of Hiler’s endeavors, this one came with a twist. The clothing line centered around polo shirts that featured silly logos. Instead of the regular alligator or polo player, these shirts had toilets, bottles of liquor or guitarists.

Hiler made a website and realized he had no money left over to actually market. “That was the flaw in the plan,” he said. Hiler’s genius for out-of-the-box stunts took over, and he recruited a few friends to fire some shotguns at mannequins dressed in his shirts. Thus was born “Shot-Up Shirts,” a line of shirts that took distressed to new levels.

The business itself never did that well — but the stunt generated plenty of buzz, including a piece in the New York Times. As Christy Hiler puts it, “The clothes piece of the idea was never that successful. It was the stunts. That’s where he discovered the power of PR.”

‘The time of my life’
Hiler loves working at Cornett — “I’m having the time of his life”– but it’s not always easy. Even when he came on board, the agency found it tough to give him a title. He still doesn’t have one. “Entrepreneurs don’t always like working under other people. That was tricky,” said Christy Hiler. “And people here have defined roles. He’s resistant to those. And it’s not the best way to use him either.”

Hiler finds it hard to explain how his brain works, but his best ideas usually begin as a joke. “I’m a fan of the weird. I see things on the Internet, and they give me ideas. I always laugh my ass off about it first, and then I think, ‘Wait, maybe I can do this.’”

Joshua Kingsland, Hiler’s creative director at Kentucky for Kentucky, says he thinks Hiler’s process is “special.” “I have felt both blessed and cursed at times to be playing a role in placing some small pieces of reality into the otherworldly, lavish and at times completely unrealistic secretions of his overactive imagination.”

When it comes to future plans, Hiler is as erratic and irreverent as his best work. No big dreams of Cannes Lions here. He wants to retire early and spend time with his kids. Until then, he wants to help Cornett grow. “When I first came to Cornett, I’ve always thought that this agency here in Kentucky could be as big or small as they want to be. Louisville is the center of the country,” he said. “We can get anywhere in the country very quick. Creativity can come from anywhere. The big agency can come from anywhere.”