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Vol.18, no.2
April/May 2015


The Good Shepherd 
Story By: Derek Ferrar

It’s New Year’s Eve afternoon on Maui, and fabled fame guru Shep Gordon is bopping along to screaming guitars as he oversees rehearsal for his annual star-studded New Year’s benefit bash. Onstage, shock-rock icon Alice Cooper’s backup band—which is serving as house band for the show—is nailing an impressive range of styles as a parade of Billboard names stops by to run through their numbers. Alice, whom Shep has managed for more than forty-five years, is on the bill, of course. So are Steven Tyler of Aerosmith, another regular; balladeer Sarah McLachlan, a first-timer; a couple of Doobie Brothers; local hero Willie K; and even clown prince Weird Al Yankovic.

Shep’s ability to garner such star power for his New Year’s dinner and show, which benefit the local food bank and the Maui Arts & Cultural Center, is testament to his reputation as one of the best connected—and best liked—figures in showbiz, thanks to his Dalai Lama-inspired philosophy of “compassionate business.” For decades the longtime Maui resident flew under the public radar: His storied feats of rock mayhem, media madness and extraordinary human kindness were kept mainly within elite circles. But then his buddy Mike Myers blew the lid off the Shep Gordon story in 2013 with his acclaimed bio-doc Supermensch. (Mensch, of course, being a Yiddish term for “stand-up guy.”)

The movie features an Entertainment Tonight lineup of megastars telling Shep stories, from pals Myers and Michael Douglas to Willie Nelson and Sly Stallone. But beyond being a loving tribute, the film is something of a meditation on the pursuit and price of fame, which Shep calls “scary” and Myers has been known to call “toxic.” At the beginning of Supermensch, Shep recalls how he used to sit new clients down, take off his glasses and warn them in dead earnest: “If I do my job perfectly, I will probably kill you.”

After rehearsing a few manic spoof songs from his latest album, Weird Al takes a break in a lobby chair, looking surprisingly, well, normal. Like many of the performers, he has a place on Maui, and this is his fourth time playing Shep’s benefit. So, does Shep really live up to his supermensch rep? “Yeah, he really is a sweetheart,” the Weird One replies. “I’d do anything for him. I’ll mow his lawn for him if he likes!” 

Maui Food Bank Development Director Marlene Rice, who is heading a crew of volunteers making decorations for the concert this evening, notes that Shep’s benefit donations have paid for close to 170,000 meals so far. On an island where ten thousand people a month need food assistance, she says, “Shep’s generosity helps make sure that no one in our Island ‘ohana goes to bed hungry.”

Growing up on Long Island, Shep (that’s his real name, by the way—shortened from his grandfather’s Shepsil) had a rough relationship with his domineering mother but was very close to his father, an accountant who himself was known as something of a mensch. 

“My father was very gentle, always kind to everyone, compassionate, put other people before him,” the 69-year-old Gordon told an audience after a screening of Supermensch at the Tribeca Film Festival. “I think a mensch walks into a room and has an awareness of where there’s need and plays into that.”