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Boston Weather: 41.0°F | A Few Clouds

A Mission To Bring Smiles To Boston

By Jiao Wang

In a city marked by subway bomb scares, high temperatures and humidity, and the usual stresses of life, one man stands in the middle of Haymarket Square in the sultry heat urging people to be happy.

“Smile, smile, smile …” says Irving Cherander, a 64-year-old, unmarried man of medium build.

“Are these free?” asks a passerby.

“What a stupid question. Why would I stand here and give away free things?”

Dressed in a beige suit jacket, Red Sox fan shirt, and blue jeans, Cherander stands next to his large black umbrella supported by a wooden stand and pole. Every once in a while, a child who runs ahead of his parents would wander under the umbrella to shade himself from the sun.

Smiley buttons adorn the front of Cherander’s jacket, adding radiance to the elderly man with blue eyes and evoking the attention of passersby. Upon the umbrella are pinned hundreds more identical smiles — two dotted eyes below which rests a long, narrow curve. The black outline comes on buttons of all different sizes and colors: yellow, red, blue, and green. At the turn of a back switch, the eyes of the smallest buttons flash red.

“They last forty-eight hours,” he tells the intermingled Bostonians and tourists. “Come back if you have a problem.”

Cherander, a vendor in Quincy Market from 1978 to 1992, first got the idea for his small business back in 1970. He was the first person to sell smiley buttons in downtown Boston, on Boylston Street where there used to be two lines across from the Copley Square public library. Over the years, he also sold many other souvenirs: stuffed animals, stuffed aliens, portraits, old newspaper collectibles, and picture frames. This summer, for the first time in more than thirty years, he is again marketing smiles.

Cherander buys three thousand buttons at a time from London for the price of 63 cents each and sells them here for two dollars. Every day this summer and possibly into the fall and winter, Cherander wakes up at seven in the morning and arrives at Haymarket Square at nine to begin a day’s work selling buttons and entertaining customers. In spite of the vendor’s tag strung visibly onto his umbrella, on some days, a noisy policeman comes and tries to force him away from Haymarket. “It is terrible in the city of Boston to have policemen driving away people who sell smiley buttons … I’m just trying to make people happy,” he says.

The buttons have come back into fashion. Commenting on the fast-paced world, the pressures of the war in Iraq, and memories of 9/11, he says that the blissful grin of the yellow smiley face seems to have the ability reaffirm hope in Bostonians. In the same way that a white dress represents virginity or the North Star a direction, the smiley face trademarks a universal expression of happiness.

These smiley buttons are night items, Cherander says, as he carefully blocks the July sun to show a tourist the flashing red eyes of a yellow smiley. His sales are best after dark, when passersby surround him to form a small crowd, eager to see the man with 10 sets of twinkling eyes on either side of his jacket and the outlines of an oversized umbrella traced by flashes of light.

Cherander reminds us that smileys were not around all the time. They were first designed in 1970 by a graphic artist named Harvey Ball who worked for State Mutual Life Assurance of Worcester, Massachusetts. In the early 1960s, State Mutual asked Ball to reinstill company morale. Ball responded by designing a happy face against a yellow background, which he first used on letterheads and stationary. Cherander says he made them yellow because “you smile when the sun is out.”

Although Ball’s idea was well-received, he never thought to copyright his design and only received $45 in payment from the insurance company. The French entrepreneur Franklin Loufrani picked up the design, copyrighting and patenting it in the process. Thus the smiley spread around the world, bestowing on its patent owner millions of dollars.

In the same way that Cherander never held a grudge against his forced evictions from vendor grounds, in his obituary, Ball’s children say Ball was never bitter about the millions he missed in life. Through the generosity of these men, the smiley lives on, destined to stir the hearts and faces of generations to come.