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Living a Legacy: James Jackson, Jr. Celebrates Provincetown’s Black Entertainment History

by Steve Desroches

James Jackson, Jr. has been on a deep dive into Provincetown history. A self-described nerd, once Jackson becomes obsessed with a topic, he’s relentless in his pursuit to learn more about it. Jackson performed in the original Broadway run of A Strange Loop, a Tony Award and Pulitzer-Prize-winning musical about a queer Black man telling a queer Black story. Throughout the run, and since, Jackson hears emotional stories from those who saw it and were moved by finally seeing themselves represented on the stage. Along the long road to Broadway the production heard time and time again that the show was “too Black” and “too gay” for mass appeal. Indeed, those critics and cynics were wrong as the show was a commercial and critical success not just in New York, but London as well, furthering the pursuit for an expansion of who gets to tell their story and where. The show made Broadway history in a field that can live up to the nickname the Great White Way. That got Jackson thinking about Provincetown.

A Massachusetts native who’s been coming to Provincetown since the 1980s, and now frequently performs on the stage and in piano bars in town, Jackson continually hears from LGBTQ Black friends in New York that while the town sounds great, “it’s not for them,” meaning there’s no space for Black queers. That perspective has long frustrated Jackson as that has not been his experience over the decades visiting Provincetown, and he wants more in the Black queer community to know that. Part of his efforts to get out the message is to shine a light on the history of Black performers who’ve come to Provincetown to be part of the town’s storied theater and entertainment scene over the decades. And the results of his research and rehearsals culminated into his brand-new show A Juneteenth Cabaret, to be presented this Sunday at the Gifford House’s performance space The Wilde.

“I found out the most amazing things,” says Jackson. “There’s that legendary summer of 1955 where in a matter of weeks Ella Fitzgerald, Billie Holiday, and Eartha Kitt all performed at the A House. That’s so amazing. There’s people who don’t know that. And there’s so much lore. How do we get the facts? Like Grace Jones at tea dance and demanding the music be stopped to find her lost earring. There’s a story that for a few weeks there was a shrine built at the Dick Dock to her lost earring. Is that just lore or is it true? I so want it to be true.”

What is true is that Provincetown has a long history of Black entertainers and artists that dates back to before the birth of the art colony in 1899. What is also true is that this legacy is not widely known, and Jackson believes if it were it could help to make Provincetown feel like a more welcoming destination for Black LGBTQ people. Jackson notes that in 1893 the Fisk University Jubilee Singers came to perform at Town Hall, while formerly enslaved people also came to town with several different jug bands or spiritual singing groups at the same time. And since then, the list of Black artists who’ve come to Provincetown includes Paul Robeson, LaWanda Page, Jennifer Holiday, James Lee Hooker, Richie Havens, Ronnie Spector, Freda Payne, Loleatta Holloway, Sylvester, Queen Ida, and more. And then there is of course the 1965 concert at the A House by Nina Simone.

A favorite singer of Jackson’s mother, Simone led him down a delightful rabbit hole as he searched for more information about her show in town, which led him to personally discovering the 1965 painting Homage to Nina Simone by Bob Thompson, who was also Black. The artist arrived in Provincetown for the summer of 1958 and came every year thereafter until 1965, when he met Simone and saw her show at the A House and then created the painting in question. And as Jackson continued to research Thompson, he found an old film of him dancing with abandon on Race Point Beach. 

“Here’s this man, who looks like me, dancing on a beach that I’ve been to looking so full of joy,” says Jackson. “It might sound cheesy, but I really believe that if you build it they will come. If you actively plan and make Provincetown more inclusive and showcase its history fully, the more diverse the town will be.”

A Juneteenth Cabaret with James Jackson, Jr. is on Sunday, June 16 at 6:30 p.m. at The Wilde at the Gifford House, 9 Carver St. Tickets ($40) are available at the box office and online at For more information call 508.487.0688. For more information on Juneteenth celebrations in Provincetown visit

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Ginger Mountain

Ginger Mountain (MS Communications Media, BA Fine Arts/Teaching Certification K-12) has been part of the graphic design team at Provincetown Magazine since 2008. Ginger has worked as a creative director, individual contractor, and freelance designer with clients representing many areas —business software, consumer products, professional services, entertainment, and network hardware to name just a few — providing creative layout and development of a wide range of print media content. Her clients ranged from small local businesses to large corporations and Fortune 500 companies, from New Hampshire to Georgia

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