That CEO smile

A new website finds art and humour in the corporate headshot

Corporate headshot, Smile, CEOThe art of the corporate mugshot is, to some, a serious business. To Gary Cutlack, a 36-year-old gaming and technology writer, it’s one big joke. Cutlack’s blog, Sexy Executives, focuses on poking fun­ of corporate photography, and occasionally offers style tips to the unfortunate subjects within.

“The thing I find most interesting about these photos is the body language,” says the soft-spoken Brit. “What I enjoy from a good executive photograph is getting the impression that they’re thinking, ‘Oh God, I really wish I wasn’t having my photograph taken, I’ve got so many better things to be doing today than standing in front of a cloudy background, trying to smile.’ But, at the same time, I get the impression that they’ve worn their nicest suit and special tie.”

Parodying corporate culture has become something of an art form since movies like Office Space and TV shows like The Office popularized the awkwardness of that world. This is something Cutlack understands. “I’ve had some pretty dull office jobs. I draw on that.” His subjects are mainly middle-aged white men sporting wan smiles, bad hair, tortoise-shell frames, and ill-fitting suits. Not exactly an appealing collection of photographs. But Cutlack’s commentary is what amuses his up to 9,000 daily readers.

“Possibly the MOST double-breasted suit money can buy. The hem must completely wrap around his waist and tie together at the back,” one post reads, describing a board member from a pharmaceutical firm. Cutlack’s dry wit is a hit with readers who frequently send in suggestions of who to take a run at next. But it’s not all moustache-cracks and suit critiques. Sometimes Cutlack offers plausible, albeit cutting, style tips. In a post about one exec suffering from male-pattern baldness, Cutlack suggests he “lose 50 lb. and shave it all off.” To make his point, he refers to “the single greatest executive makeover of all time”—of J Allard, a chief technology officer at Microsoft who shaved his head, lost weight, and now resembles a dapper, sophisticated Michael Stipe. “Seriously, you could pull this off,” he tells his target. “Buy a mountain bike, then start experimenting with more expensive shirts. They really do fit better.”

It might be funny, sure, but isn’t it all a bit rude? “I don’t think I’ve ever really been too offensive to people,” says Cutlack. Even still, there have been protests. “One woman went a bit crazy and filed a copyright takedown notice because she said I wasn’t allowed to use her photograph.” Google, who hosts his blog, forced him to take it down. But Cutlack, who works from home on the Isle of Mull, a tiny island off the coast of Scotland, emphasizes that no one should be taking him too seriously. “It’s just me mucking about with a few silly photographs of men in suits. It’s something I do to amuse myself.” And thousands of others, apparently.