Alan Cumming, the award winning actor, best selling author and activist, is taking a road trip to the Vineyard. Like many who make their way to the Island in the summer, he plans to relax on the beach and visit with friends. He will also perform a cabaret show of sappy songs at the Old Whaling Church.

As a part of the inaugural season of the Martha’s Vineyard Concert Series, Mr. Cumming joins acts including David Sedaris, Amy Goodman, Chadwick Stokes, the Preservation Hall Jazz Band and more to bring comedy, songs and storytelling into the summer months. His show is Thursday, July 14, at 7:30 p.m.

Mr. Cumming created his current show, entitled Alan Cumming Sings Sappy Songs, a year ago during a highly emotional time in his life. He had recently turned 50 and published a memoir that explored his relationship with his abusive father. In creating a new work he wanted to delve into those emotions, so he turned to songs that made him feel. And feeling is what makes a song sappy, he says.

“For me it’s about a song that when I sing it something in my heart twinges, there’s something emotionally I connect with,” Mr. Cumming told the Gazette in a recent phone interview. “It could be the chord sequences, but it’s usually the message of the song.”

Meaningful messages transcend musical styles and Mr. Cumming reached across many genres to create the show. One source of inspiration was Club Cumming, the dressing room after-party he hosted while starring in Cabaret at Studio 54. He would deejay, playing pop songs that nobody would expect a Tony-award winning actor to sing. But Mr. Cumming didn’t get to where he is by doing what people expect. As a classically trained actor, he has starred as Hamlet and Macbeth while also voicing a Smurf. He’s appeared in a Stanley Kubrick film and a Spice Girls movie back to back. The Scottish actor easily jumps between blockbusters, independent films, stage and television — most recently, in The Good Wife.

“I take my judgment hat off and connect to the songs emotionally” he said about his current show. “When I first sing the songs in the show I get a little titter. I like that, because I know by the end of the show it will be different. I’m asking people to be more honest and authentic.”

He will sing songs by Miley Cyrus, Billy Joel, Stephen Sondheim and Rufus Wainwright. Also in the line up is an Alan Cumming original. Mr. Cumming will perform with cellist Eleanor Norton and long-time collaborator and Emmy-winning musical director, Lance Horne. The show is as varied as Mr. Cumming’s career, one that has often been described as eclectic.

“It’s a true cabaret, there’s thought provoking things, sad things, it’s a real smorgasbord of forms,” he said. “We go on a journey together, you shed a tear, you laugh a lot and you think new things.”

And one of the new things audience members will think about?

“Me, me, me, me,” Mr. Cumming said. “They are definitely going to find out more about me than they ever wanted to.”

Alan Cumming performs at the Old Whaling Church on July 14 at 7:30 p.m. Tickets and more information about the MV Concert Series are available at: mvconcertseries.com.