'I Can Sing That.' 'Strange Loop' Alum James Jackson, Jr. Connects with Favorite Songs for Ptown Cabaret

While "A Strange Loop" was playing on Broadway, James tweeted once that the role he wanted to play was the Baker's Wife in another Sondheim show, "Into the Woods." "Whatever I said, pissed people off," he recalls. "I got these angry tweets, and I thought, 'Oh my God. I've arrived!' That they were so offended by a make-believe tweet is funny to me." But it also gave James the resolve to sing the Baker's Wife endearing solo, "Moments in the Woods," but from his point of view. "I tell that story. And I tell a story of me meeting Bernadette Peters backstage at the Tonys, and her answering me in a tweet wanting me to sing this song. And people have said, 'Wow, I just I never heard it put that way.'"

James grew up in Randolph, a suburb of Boston, and recalls going to Provincetown all his life. "I remember as teenager, if one of my friends could drive and had a car, we'd head there. And we really didn't know why. But in hindsight, I think it was this big gay magnet that was pulling us there." But when James moved to New York, he found many of Black friends were not fans of the popular gay resort. "I have these friends in New York, these other artists of color, just performers and writers of color who don't understand why I travel to Provincetown so often. They always say that Provincetown just isn't for them. It's not for us. And that makes me so angry. I get, like, enraged by it, because that's never been my story. I've always felt so welcome there, and part of my own history is feeling part of that town."

Such was the genesis of his "A Juneteenth Cabaret," which he presented at the Gifford House's performance space The Wilde this past June, in which he looked back at the many Black performers who played Provincetown over the years. "I keep getting back to the amazing summer of 1955 where, over a four week period, Eartha Kitt, Ella Fitzgerald, and Billie Holiday all happened to play the A House. And I was like, 'What? How is this? How do I never know this?'" He added that many of singers' band members were not allowed to stay in town, so the families of the Portuguese fishermen took them in. "What they did speaks of Provincetown as a caring community that takes care of others."

He also learned in his research for the show that Kitt fell in love with the town and recorded a live album at Town Hall in 1988 or 1989. Also, that Nina Simone played there a number of times. And then there was Grace Jones, whose visit to Provincetown is famous for when she visited the Boatslip for T-Dance and lost an earring on the dance floor. She made the DJ stop the music so her entourage (along with everyone on the dance floor) could search for it. They didn't find it, and believe it fell beneath the deck, amongst the piling of the deck – which, coincidently, is the location of the Dick Dock, a well-known after-hours cruising area. "The lore around Grace Jones is that after no one found her earring, someone built a shrine at the Dick Dock commemorating that was the spot where Grace Jones had lost it. The shrine stayed there a couple of weeks. I don't know if it is true or not, but I think it a hysterical example of how lore can spread."

What James has always loved about Provincetown is its freedom. "It is a place where people are free to do whatever. And I think that's excellent to have a place anywhere on this planet that you could do that."

What he loves about performing is gazing out at an audience. "I have the best view in the world, whether it's on Broadway or at a small cabaret space in New York, or Boston, or in Provincetown. I get to watch people receive something. There is no greater joy in the world. And I kind of, I wish it on everyone. It is such a really cool thing. So if I am just getting up there to sing things, and under the guise of, 'Hey, I was told one time I shouldn't sing this.' So, here it is, and then you enjoyed it. Then I did my job. I did my job."