Sing a sappy song with Alan Cumming

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Alan Cumming — Gareth Easton

It wouldn’t surprise me if the last thing you watched on TV had Alan Cumming’s name listed somewhere in the credits. Known for his standout performances in television, film, and theater, as well as writing and producing, the four-time Emmy nominee and Tony awardwinner is a familiar face in show business. This past year, Mr. Cumming has brought his talents on tour, testing an onstage role he’s yet to try: Himself.

In an old-fashioned cabaret show, “Alan Cumming Sings Sappy Songs,” Mr. Cumming will bring laughs, songs, and stories to the Old Whaling Church in Edgartown on Thursday, July 14. Alongside his musical director, Lance Horne, and cellist Eleanor Norton, Mr. Cumming tells stories meant to make you laugh while plucking at the heartstrings.

“The show is quite eclectic, like myself,” Mr. Cumming said in an interview with The Times.

In the breaks between filming his television series “The Good Wife,” Mr. Cumming allotted time to be on tour. He’s brought his show to venues all over Australia, Canada, and the United States since its debut in New York last summer. He plans to attend the Edinburgh International Festival in Scotland this August, where the show will finally hit his homeland. This will be his first time performing on Martha’s Vineyard, and his second time visiting.

“I like this tour a lot, because everything is so spread out,” Mr. Cumming said. “Each time I go to do a show, it still feels special, it feels fun, and it doesn’t feel like work.”

Intimacy is the most important aspect of this show. Mr. Cumming wants the audience to feel connected and comfortable, so he tries to create an honest and open atmosphere where everyone feels like they know him in a way. In the past, bits of the show have been interactive and improvised. Some extensive experience in standup comedy has Mr. Cumming armed with one-liners.

“I like that feeling of being on your toes, being sharp and responding to a moment where the audience engages in a certain way,” he said.

In a performance in Austin, Texas, last week — one of Mr. Cumming’s favorite U.S. cities — he found himself complying with audience requests and opening up the floor for conversation. “Wait, I thought this was my show,” he said at one point. But all in all, captivating the audience is the aspect of the show that Mr. Cumming likes most.

Since it’s all about connections, Mr. Cumming and his band have some preperformance rituals to keep themselves aligned with the show’s purpose. Before going on stage, everyone locks eyes, keeps eye contact, and wags a finger in front of one another. “It’s a weird, funny thing, but we have to do it,” Mr. Cumming said. And if they forget, they’ll flag one another offstage to sync back up. Rituals are rituals.

Originally from Scotland, Mr. Cumming lives in New York City with his husband and two dogs. “I love living in the city,” he said. “Every single time I walk out of my building, it feels like a new adventure begins.”

Whether you’ve loved him all your life, recognize his name, or only know him as the villain in some of your favorite guilty-pleasure movies — including “Spy Kids,” “Josie and the Pussycats,” and “Spice World” — Mr. Cumming knows how to put on a show, and he’s endlessly excited to entertain.

“Each time I do the show, there’s a different energy,” he said. “I look forward to the challenge of walking into a room of people I don’t know, discovering the mood, and taking it from there.”

While on the Vineyard, Mr. Cumming anticipates the challenge of keeping up a vegan diet among a population of seafood-fueled Islanders, but like all of us, he is most excited to get to the beach, swim in the ocean, and hide under an umbrella for a few hours.

“Alan Cumming Sings Sappy Songs,” presented by Martha’s Vineyard Concert Series. Thursday, July 14, 7:30 pm, the Old Whaling Church, Edgartown. Tickets start at $125 and can be purchased at mvconcertseries.com.