Stillpoint is asking the Vineyard to say “yes, and” to a night of improvisational comedy for its second annual fundraiser.

Laughing Matters, a star-studded night of long-form improvisational comedy from Bluebird Improv, will take place at the Martha’s Vineyard Regional High School Performing Arts Center on July 18, with proceeds from ticket sales supporting the nonprofit.

Stillpoint opened its doors in late 2024 as a venue and launchpad for public educational programming and events, from community suppers and soundbaths to lectures and workshops. Stillpoint’s Friday Night Forums invite members of the public to discuss the far-reaching issues of the day.

When asked to distill Stillpoint’s essential mission, assistant director Allison Simon laughed. She said it’s a question that has been challenging to answer given that openness is its ethos.

“I think Stillpoint is an invitation for people... to think about what it is that they have to offer others and then to come and offer it,” she said. ‘We encourage discourse here. It’s something of an experiment in community building.”

Founder Thomas Bena, who sees Stillpoint as a “reimagined community center,” has been impressed by Stillpoint’s growth over the past year and a half. Fundraising, he said, will help the young organization to catch up with that growth operationally.

“I feel like we’ve kind of made a go-kart,” Mr. Bena said. “We’ve been pushing it on flat land, and this year it’s like we’re going down a hill, and we realized the wheels are kind of loose and we’ve got to tighten the bolts.”

Bluebird performed at Stillpoint for last year’s fundraiser. The group specializes in long-form improv — a style of play that differs from the quick series of segments many remember from Whose Line Is It Anyway? Using a “suggestion” from the audience, long-form improvisers work in tandem to act out a series of unscripted comedic scenes, often woven together in surprising ways.

This year’s cast includes Joe Canale, Tim Meadows, Brad Morris, Marc Evan Jackson and Matt Walsh.

Mr. Jackson, a Bluebird cast member who audiences will recognize from Brooklyn Nine-Nine and The Good Place, spoke with the Gazette about the thrills of bringing the art form to audiences. He started doing improv as a college student in 1994, before going on to work with renowned improv theater The Second City and Detroit-based troupe The 313. He and his wife, Beth Hagenlocker, started the Detroit Creativity Project, which brings improv to students at Detroit’s public schools.

For Mr. Jackson, being able to flip an audience suggestion into comedy is something akin to sorcery.

“It truly feels like a highwire act, and a bit of a magic trick,” he said.

Bluebird gets its suggestions by conversing with audience members and mining stories they tell for scene ideas. He has some words of advice for those chosen: be incredibly specific, but be honest.

“Tell the truth,” he said. “Don’t amplify anything, don’t exaggerate anything.”

He’s encountered his fair share of skeptics, who are convinced he and the other performers scripted the show beforehand and somehow tricked the audience into offering a specific suggestion.

“We promise, we’re making it up,” he said. “We’re not mentalists.”

An improv background has been foundational to Mr. Jackson’s work as an actor, but it’s not just performers-by-trade who can benefit from practicing the art form.

“Everybody in the world should take an improv class,” he said. “It’s practice at accepting uncertainty, and failing, and realizing that failure is not a lasting or fatal condition.”

“We’re improvising every moment of every day,” he added.

For the team at Stillpoint, improvisational comedy and growing a nonprofit have more in common than meets the eye.

“What we’re doing is improv,” said board clerk Bill Russell. “We’ve made mistakes, and we’ve adjusted, and we’re moving forward with our mission in mind.”

Ms. Simon added that improv, much like Stillpoint, only works with participation from the public. Just as improvisers accept and build on suggestions, Stillpoint’s programming model relies on ideas from the community.

“We’re here to be interactive, to collaborate,” she said.

Stillpoint moved this year’s fundraiser from its home in West Tisbury to the high school’s Performing Arts Center to accommodate more guests and introduce tiered ticket prices, making the event more accessible.

For Stillpoint treasurer Scott Fish, helping as many people as possible access the space — and fill it with the gifts they have to offer — is the goal.

“I think every person that has come here has felt something magical and special and powerful,” Mr. Fish said. “When they come here, they get it.”