Alan Cumming was quick to tick off the things he loves about being in Maine – biking, taking a boat ride to the Isles of Shoals, and having dinner with his friend and fellow entertainer Caroline Rhea at her southern Maine home.

The Broadway, TV and film star was also quick – and decisive – in identifying his least favorite thing about Maine.

“My least favorite thing is answering dopey questions about what’s my least favorite thing about Maine. What’s not to like?” said Cumming.

Cumming has spent a lot of time recently, and over the years, finding out what he likes about the state. This summer, he spent time in Kennebunkport, performing at Club Cumming on the Coast at the Kennebunkport Inn, a summer edition of his Club Cumming cabaret bar in New York City. He’s coming back to Maine to perform Friday at Merrill Auditorium in Portland with National Public Radio’s Ari Shapiro in a show called “Och and Oy! A Considered Cabaret” presented by Portland Ovations. 

He’s come to Maine several times over the years to visit a sister-in-law in Falmouth. And he says he hopes Club Cumming at the Coast will continue for some time, though he hasn’t finalized details yet. This year, Club Cumming shows have been held on weekends at the Kennebunkport Inn. They started Memorial Day and are scheduled through October. Cumming has a friend involved with the Kennebunkport Resort Hotels, which includes the inn.

Cumming performed there in July, with Shapiro, but most weeks the shows featured regulars from his Club Cumming in New York. The series raised more than $25,000 for The Actors Fund, which helps entertainers dealing with health or financial issues.

Alan Cumming and Ari Shapiro will perform in Portland Oct. 22. They performed in Kennebunkport over the summer. Photo by JJ Geiger

Cumming, 56, was born in Scotland but has been well-known to American audiences for more than 20 years. He won a Tony on Broadway as the master of ceremonies in a 1998 revival of “Cabaret” and has been nominated for three Emmy awards for his role as political consultant Eli Gold on the CBS drama “The Good Wife” from 2010 to 2016. His film credits include “Romy and Michele’s High School Reunion,” “The Anniversary Party” and the “Spy Kids” adventure series. Cumming and Shapiro, who is host of NPR’s “All Things Considered,” started performing together in 2019 with an act that includes songs, old and new, and personal stories. Shapiro has been a guest singer with the jazz/pop orchestra Pink Martini for more than a decade.

Cumming agreed to answer a few emailed questions ahead of his appearance at Merrill Auditorium with Shapiro. He responded to some in writing and others by recording his answers and emailing the audio clips to the Press Herald. (Yes, he has a cool Scottish accent.)

Q: How did you and Ari Shapiro team up to perform together?

A: Our relationship first started out as a radio newsman interviewing an activist performer from stage, TV and film – now we are cabaret co-stars. I realized our chemistry and the unusual combo of us, as well as the fact that Ari has an amazing voice, would make for a really great cabaret show.

Q: Can you give us an idea of what your show with Ari is like? What songs you might do? What you might talk about?

A: My show with Ari Shapiro is a cornucopia of song and story. It’s really a very old fashioned kind of cabaret. It’s me and Ari with a piano – our musical director is called Henry Koperski – and it’s just us talking about how we met, things we share and sort of talking about how though we may seem like very different, disparate people, we actually are quite similar. We’re both storytellers, we both have a love of cabaret, and we’re both sort of fascinating queer men. And we just get on really well and we wanted to take our show on the road and maybe surprise people a little.

Alan Cumming, at his Club Cumming New York, will be performing in Portland Oct. 22 with Ari Shapiro. Photo by CBS Watch/Timothy Kuratek

Q: Why did you want the Kennebunkport Inn to be the location of your summertime Club Cumming this year?

A: I thought it’d be great if Club Cumming brought a little spice and mischief to Kennebunkport. We all need a bit of fun and joy in our lives, so this fusion of two seemingly disparate cultures, the East Village and Kennebunkport, makes for a really special experience. I wanted to create a place where people feel safe and comfortable and they could see things that maybe they wouldn’t expect to see, maybe have their horizons broadened.

Q: Do you think Club Cumming in Maine will be a regular thing?

A: We’re talking about the possibility of Club Cumming returning and having another presence in Kennebunkport. It certainly was a lovely experience all round, I think. So yes, that’s in the cards. We’re in discussions, hold the front page.

Q: If you were to live here, what would be your idea of a dream Maine house and location?

A: In terms of, if I were to stay permanently, my idea of my favorite home, I think it would be to live with Caroline Rhea (an actress and comedian who has a home on Maine’s southern coast). We went to her house for dinner and had such a lovely time. She’s had a house in the area for ages because she’s Canadian. A lot of Canadian people come down to Maine because it’s the closest place to the sea or something, she said. Anyway, I think I’d like to just move in with Caroline Rhea.

Q: What did you do while in Maine this summer, besides perform? Did you have a favorite spot or two to visit? A favorite activity?

A: This summer when I visited Kennebunkport I went on a little boat to Star Island in the Isles of Shoals, had a grand day. That was great, I love a little boat trip. We stayed at – where did we stay again? – at Hidden Pond (Resort in Kennebunkport), and that was absolutely glorious. I loved running around on bicycles. I’ve come to Maine over the years because my sister-in-law lives in Falmouth, so I’ve been there quite a lot. It was nice to go to Kennebunkport, my first time, and it did not disappoint.

Alan Cumming brought his Club Cumming to Kennebunkport this summer and will be at Portland’s Merrill Auditorium Oct. 22. Photo courtesy of Navadise Media

Q: You’ve raised a lot of money for the Actors Fund with Club Cummings shows in Kennebunkport. Why is the cause so dear to you?

A: As someone whose career first began working in TV, films and theater, the arts play a huge role in my life, both personally and in my business ventures. It’s been really sad watching so many venues, especially the old venues that have been around for generations, having to close over the past year. It shows just how volatile and precarious a life is trying to keep a bar or stage open, especially a queer one.

This partnership is more than just an opportunity to recreate this beloved NYC destination in Kennebunkport, it is an effort to save our stages by creating new ones. Club Cumming on the Coast has partnered with The Actors Fund, to support the national human service organization’s ongoing effort to support arts professionals who have been especially impacted by the COVID-19 pandemic. Since March 18, 2020, The Actors Fund has provided more than $20 million in emergency financial assistance to thousands of individuals across all 50 states and Puerto Rico.

Q: What is your favorite thing about performing at Club Cumming, either in Maine or in New York?

A: The cabaret clubs of Berlin blossomed in the Weimar Republic after the first World War, in that boomtime after the Spanish flu. That’s where the musical “Cabaret” has its origins, and that’s what Club Cumming is an homage to in its design and aims. It has been a bastion of equality, fairness and anti-racism. It is always fun to bring a show with so much spice to new environments, pushing each other to step outside of our comfort zones and sharing the Club Cumming spirit, reminding everyone that they are always welcome at our shows.