“H.M.S. Pinafore” Uptown, on Repeat

A century ago, some Manhattan blue bloods in Blue Hill, Maine, decided that performing Gilbert and Sullivan would keep the kids out of trouble. They’re still at it.
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Illustration by João Fazenda

A hundred years ago, four moneyed New York families were summering in Blue Hill, Maine, including Dr. Seth Milliken and his wife. “A movie theatre had opened up in town, and they wanted to protect their children from this corruptive influence,” Joanne Lessner said the other day. To keep the youngsters out of trouble, the story goes, a house guest suggested mounting a production of Gilbert and Sullivan’s “H.M.S. Pinafore.” “They performed it on the Millikens’ schooner, and all the Pierce-Arrow cars were lined up at the docks with their headlights on, and that was the lighting,” Lessner recounted. “A piano and violins floated on a dinghy nearby. It stormed, and the piano almost washed overboard—but the troupe was born.”

The troupe is the Blue Hill Troupe, which now boasts some four hundred active members and stages a Gilbert and Sullivan operetta every spring. The proceeds go to charity, as decreed by its charter, which is written in rhyming verse. In the troupe’s early decades, it drew blue-blooded Upper East Siders—by 1926, its shows had moved to New York, with a rendition of “The Pirates of Penzance” at the Millikens’ Madison Avenue mansion—but it now welcomes what “Pinafore” calls the “lowly born,” alongside a descendant of J. Pierpont Morgan. The members, both “backstagers” and “frontstagers,” range from professionals to enthusiastic amateurs. “We have lawyers, we have baristas,” Lessner, who joined in 1997, said. “We have a retired C.I.A. agent.” The troupe attracts “like-minded people,” she explained, meaning hams who can toss off the lyrics to “I Am the Very Model of a Modern Major-General.”

Lessner, who writes musicals and detective novels by day, was playing Josephine in the centennial production of “Pinafore,” in April—which will be reprised in Maine in August, this time on dry land. Troupers describe the group as a “second family,” but its ranks are full of actual kin. To date, there are a hundred and two “met and marrieds”—couples forged in the troupe—and parents drag in their kids. Lessner is part of a three-generation clan of troupers. Her mother, Helen, a former ad copywriter, saw her first troupe show, “The Yeomen of the Guard,” in 1954, and she joined the chorus starting in 2000. In 2010, in “The Gondoliers,” she played Inez, who “solves the plot with a lovely recitative,” Helen recalled, over family dinner before a rehearsal. “My husband joined shortly after I did, and he was a backstager,” she added. She was singing in “Pinafore” alongside Lessner’s children, Julian and Phoebe. Lessner’s husband, the Broadway conductor Joshua Rosenblum, would not be participating. “His jam is the Russian composers—Prokofiev, Shostakovich—so for him Sullivan is a little bland,” Lessner said.

Lessner was six when Helen brought her to her first Blue Hill show. “I grew up a Gilbert and Sullivan addict,” she said. “I would make my babysitters listen to me while I put on the records and sang all the parts.” “Pinafore” is her thirteenth troupe show and her second go-round as Josephine, the captain’s daughter who falls for a humble sailor. “Of all the Gilbert and Sullivan heroines, I think she’s the juiciest,” she said.

Her son, Julian, a software engineer and a comedy writer, said, “I was like my dad, not super into Gilbert and Sullivan growing up. But then when I was twelve they did ‘The Sorcerer,’ which has a part for a little kid, and my mom was, like, ‘You have to audition.’ ” His fiancée, Sabrina, whom he met on Hinge, was in last year’s production of “Pirates.” They played a pirate-and-maiden couple; Helen was the assistant stage manager. “Every G. & S. show ends the same way: everyone gets married to whoever is nearby,” Julian said. “I texted, like, ‘Hey, Grandma, can you make sure Sabrina and I get paired up?’ ” He compared the troupe to “a very specific Hinge.”

Had the troupe fulfilled its original purpose of keeping the kids out of trouble? “I’m a pop-rock singer-songwriter, so we’re still rebelling,” Phoebe, who graduated from college last year, said. “It’s such a shame that Gilbert and Sullivan aren’t alive to have TikTok. If more Gen Z knew about them, they’d want to join a group like this.”

A few weeks later, all four were onstage at El Teatro of El Museo del Barrio, an Art Deco auditorium with dreamy muralled walls, on upper Fifth Avenue. Many in the crowd were longtime troupers, including Win Rutherfurd, a retired estate lawyer who’d relinquished the part of Captain Corcoran after a health scare. “This would have been my forty-second principal role,” he said. One of the troupe’s traditions is to cap rehearsals with a trip to a local watering hole, ending with a rousing chorus from “Pirates”: “Hail, Poetry, thou heav’n-born maid! / Thou gildest e’en the pirate’s trade.” ♦