Diane Sullivan
Diane Sullivan Credit: Matthew Thorsen

Cofounders Pamela Polston and Paula Routly scrimped, scrounged and labored to bring Seven Days into the world. And when their baby finally arrived, they took one look at its cover and cringed.

“Paula and I were both just so appalled,” Polston remembered.

It was “hideous,” Routly agreed.

That first issue, published in early September 1995, had a back-to-school theme, so Polston and Routly hired a guy they knew to take a picture of lockers, which they published in black and white. “A) It was a really boring photo,” Polston said. “And B) it just turned to total mud at the printers.”

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The cofounders “watched in horror” as the “way-too-gray lady” rolled off the press, Routly said.

But there was great stuff inside the issue, and the covers quickly improved.

Among the hundreds of awards Seven Days has collected in its 30 years are many (we haven’t counted) given for design. Most recently, in July, the Association of Alternative Newsmedia awarded Sean Metcalf first place for his illustrations for our 2024 Daysies awards magazine.

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Seven Days’ cover is the fresh face it puts on each week to greet the world. It needs to be eye-catching, relevant to the issue’s content and able to convey a message at a glance.

Lars-Erik Fisk was art director for the first year, creating the newspaper’s look and designing its early covers. When he left to pursue a career in sculpture, he passed the torch to Jim Lockridge of Big Heavy World, who subsequently handed it to Samantha Hunt, then a recent University of Vermont grad. For two years she designed the paper and also wrote for it on occasion. Hunt has since held a design job at the Village Voice and published several books.

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Current creative director Don Eggert, who joined the paper in 1998, has designed a slew of covers. For the past decade-plus, the job has largely fallen to Diane Sullivan, 56, who joined Seven Days in 1999 and became art director in 2006. Sullivan thinks with a pen in her hand, doodling during meetings.

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Human-interest stories featured on the cover often get illustrations. Sullivan sketches a concept, hands it off to an illustrator and lets them render her vision in their own style. She rarely asks for changes. The tattooed lead singer in the company house band Enemy of the People, Sullivan is as colorful and relaxed as the kimono jackets she wears to the office. She was married to Matthew Thorsen, our longtime staff photographer, until he died in 2019.

For Sullivan, aka “Sully,” news covers pose a creative challenge. Serious stories that make the cover usually require a photograph, a bit straightforward for someone who uses “Wacky!” as a compliment.

Sometimes Sullivan wriggles out of it. On February 11, 2015, the Burlington mayoral race was supposed to go on the cover. S-news-ville!

A sampling of Sullivan’s doodles and the final covers
A sampling of Sullivan’s doodles and the final covers Credit: File

“I mean, I know it’s important,” Sullivan said. But that issue also included a story about the 20th anniversary of the Winter Is a Drag Ball, then produced by the beloved drag queens of the House of LeMay. So Sullivan suggested putting them on the cover telling people to vote, an actual cause for which the LeMays advocated. Illustrator Marc Nadel produced caricatures of the queens toting signs that said, “Make Up your mind and VOTE!” and “ReDress Your Grievances — VOTE!” and a balloon emblazoned “House of LeMayor.”

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Nadel is among several nationally known cartoonists and illustrators whose work has appeared on Seven Days covers. Others include Alison Bechdel, Harry Bliss, Jeff Drew, James Kochalka and the late Ed Koren.

Early on, artists were limited by the fact that only one color could be added to an otherwise black-and-white cover. And for the first 14 years, the paper was folded, challenging designers to fit the most pertinent information above the fold so it would be visible on the newsstand.

The fold also presented the sort of opportunity an alt-weekly is compelled to seize. In 2007, when readers voted Rusty DeWees the Vermonter they’d most like to see naked, Seven Days delivered. The Logger’s mirrored shades, cheeky grin and sculpted torso appeared above the fold. Readers had to pick up the paper to see more.

A sampling of Sullivan’s doodles and the final covers
A sampling of Sullivan’s doodles and the final covers Credit: File

Covers have certainly stirred controversy, Polston said, noting that the paper’s annual theme issues used to include one on sex. “We were — and still are — in the alt-weekly family, and we were always trying to go for something not necessarily provocative but definitely edgy and creative.”

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Like interactive covers. For the 2011 Sex Issue, headlined “In and Out,” the cover featured a certain hand gesture and included instructions to fold Line A to meet Line B to complete the motion. Award-winning publication designer Robert Newman named it one of the top 10 alternative newsweekly covers of the year, and Sullivan counts it among her favorites.

Picking those now is like trying to pick a favorite child. That first ugly baby is tucked away in the archives, and so many more have come along, each lovable in its own way. Well, that’s the goal, anyway.

“They can’t all be super-duper winners,” Sullivan said, but they’re only out for a week. As of this writing, she had not created the cover for this issue. Hopefully, it lands in the “wins” column.

If not, she gets another crack at it next week.

A sampling of Sullivan’s doodles and the final covers
A sampling of Sullivan’s doodles and the final covers Credit: File
Credit: File

The original print version of this article was headlined “Cover to Cover | The “wacky” wisdom behind Seven Days’ cover images, from photos to illustrations to suggestive foldable art”

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Mary Ann Lickteig is a feature writer at Seven Days. She has worked as a reporter for the Burlington Free Press, the Des Moines Register and the Associated Press’ San Francisco bureau. Reporting has taken her to Broadway; to the Vermont Sheep &...