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Yoop and Behold: The Creative Energy and Endeavors of Bugsy Sailor

by Jennifer Vosters

A person wearing a red winter coat and bright hat standing in the street as snow falls. They are holding up a cardboard sign with sharpie text that reads "watch more sunrises"
Photo Credit: Courtesy of Bugsy Sailor
“From a young artist standpoint, I hear about a lot of hesitation in putting your work into the world, the vulnerability that requires,” he acknowledges. “Just do it. Just get that project going.”

This artist, entrepreneur, and “Official Unofficial Ambassador to the U.P.” is on a mission to uplift the Upper Peninsula through quirky creativity and human connection.


Bugsy Sailor is a “doer of things.” 

Sunrise photographer. Festival co-founder. Business owner, web designer, holiday inventor. Above all, a Yooper. That’s someone who lives in the Upper Peninsula—“U.P.”—of Michigan.

“We really latch onto the word ‘sisu,’ a Finnish word meaning ‘resilient,’” says Sailor. Physically separate from the rest of the state, the U.P. “is its own little subculture” of resilience, resourcefulness, and the great outdoors. 

Sailor makes it his life’s work to expand and celebrate that subculture. No idea is too small…or big.

“A big driving force of a lot of my work,” he says, is “using the quirky to bring people together.”

A large group of people all wearing plaid-patterned clothing posing together.
Photo Credit: Courtesy of Bugsy Sailor
“I like to connect with people over all these different subjects, make someone smile with it, get people together in a big way,” he says. Here’s the 2019 Plaidurday celebration.

Like Plaidurday, a “worldwide” celebration—founded by Sailor—of the U.P.’s (unofficial) pattern with suggested activities like wearing plaid, making plaid cookies, and donating plaid clothing to shelters.

Or 906 Day, another Bugsy Sailor original, which encourages Yoopers to celebrate their area code by sharing photos with the hashtag #906Day annually on September 6.

Or the dating site Yooper Singles.

Or about a dozen others.

“I don’t like sitting on ideas,” he says. “We all have little ideas that surface. Hopefully, people see my work and think, ‘Oh, I should start that little quirky idea I had.”

 

“What I think we’re blessed with here in the U.P. [are] communities that are willing to say yes,” he says. “That ‘yes’ mentality is really important.”

BUGSY SAILOR

Shining Bright for the U.P.

As his friend group’s “token Yooper” at Michigan State University, Sailor discovered a passion for sharing all things U.P.: the lakes, the plaid, the people. He earned degrees in advertising and sociology and started working in web design. “It was always this enjoyment of the worldwide web, which I’ve latched onto for the core of most of my projects,” he says.

Sailor’s best-known project is Year of the Sunrise

He wakes before dawn to photograph sunrises in blizzards, downpours, and clear skies on the shores of Lake Superior. He’s amassed a following on social media and was featured on CBS Sunday Morning. “I don’t think I ever imagined this whole sunrise endeavor to strike a chord with as many people as it has. I feel incredibly blessed.”

Sailor publishes his photos online and one day, hopefully, in a book. He’s in his 8th year of documenting sunrises.

He sells prints at his business in downtown Marquette, the Upper Peninsula Supply Co., which carries a trove of Yooper merch including original designs by Sailor. One example is his Marquette Salamanders gear, a “semi-fictional sports team” Sailor invented to celebrate the blue-spotted salamanders that migrate through the area. 

Then, there’s Fresh Coast Film Festival, a first-of-its-kind documentary fest co-founded by Sailor. Film buffs and outdoors enthusiasts unite to explore Marquette’s natural beauty by day and enjoy cinema honoring the “outdoor lifestyle, water-rich environment and resilient spirit of the Great Lakes” by night.

A large audience of people sitting in chairs, all facing one direction under a large tent-like structure.
Photo Credit: Courtesy of Bugsy Sailor
Fresh Coast Film Festival, supported in part by the Michigan Arts & Culture Council and National Endowment for the Arts, is held in Marquette each October. It also hosts pop-ups in other cities across the state.

“What I think we’re blessed with here in the U.P. [are] communities that are willing to say yes,” he says. “That ‘yes’ mentality is really important.”

Sailor’s creative endeavors in service of the U.P. have earned him a title: Official Unofficial Ambassador. “I’m still waiting for a nod from the governor,” he chuckles. 

But until then, he’ll keep “repping the U.P. in a fresh and unique perspective,” he says, and “putting a little more fun and joy into the world.”