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Mixing It Up

James Jackson, Jr. Delivers at the Post Office Cabaret

by Steve Desroches

It was one of those “I have a feeling we’re not in Kansas anymore” moments. Actor and singer James Jackson, Jr. arrived in Branson, Missouri, for a two and half month run in Christmas Dreams, a “knock off” of the Radio City Musical Hall Christmas Spectacular, of which he’d been a cast member previous holiday seasons. He was playing a poinsettia tree that falls in love with a snow woman. Poinsettias don’t grow on trees, but they don’t sing or dance either, laughs Jackson, so who cares. As an actor, a job is a job. The over-the-top storyline wasn’t what was so disorienting about the Ozark Mountain tourist hot spot, but rather the unsuspected culture shock even though he was in his own country. Branson is a favorite destination of conservative white evangelical Christians. As such, in addition to the Hollywood Wax Museum and a replica of the Titanic, Branson also is home to 45 theaters that over the years have attracted acts like Pat Boone and Anita Bryant, while also offering multiple Christian-themed musicals and other conservative fare. Russian-born comedian Yakov Smirnoff has his own theater, too. But mixed in with all the uber conservative visitors is a huge gay presence, albeit a hidden one, with all these performers from all over the world in town. Again, a job is a job is a job. While those were strange days, Jackson certainly doesn’t regret it as he made lifelong friends during that intense experience. And it was kind of an adventure to go someplace so radically different than his Massachusetts childhood and New York life as an adult.

“It’s a really freaky place,” says Jackson. “But I say just go. Really, I mean it. It’s just so weird you have to see it for yourself. Stay just a weekend, but you’ll have memories for the rest of your life. It’s just so weird. When my mother came to visit she took the bus from Springfield and when I picked her up she gave me a big hug and said, ‘I haven’t seen another Black person for four hours!’”

With wit and empathy Jackson is a master storyteller. He maneuvers life with a keen interest as he explores the human condition, applying it to his work. That brief time in Branson as a dancing poinsettia tree is of course memorable, but it’s his collective life experiences that continually fill his font of creativity from which to pull. His ability to observe and connect makes Jackson particularly primed for cabaret, that intimate art form of song and stories that requires a certain vulnerability for a show to be successful. And come the first weekend in October he’s bringing his cabaret show Mixtape to the Post Office Cabaret, one of his first forays back into live performance since prior to the pandemic.

Life on the stage, pandemics aside, is a wild ride. And Jackson laughs as an introduction before relaying a particularly memorable moment. Having grown up in Randolph, Massachusetts, Jackson was very familiar with Provincetown from a young age, visiting first with his family as a child and then on his own as an adult gay man. It’s only recently that he began to perform here, starting at Tin Pan Alley, where he’d sing for a three-hour stretch for a crowd that comes and goes, and might chit chat throughout. That’s no problem. But he learned quickly that those that come often communicate their mood. Perhaps they’re celebrating an anniversary or a birthday. Others are more somber reflecting on a recent death of a loved one or struggling with a recent serious diagnosis. Often like the realm of the bartender to be part-time counselor, a performer in a piano bar often takes the role, too. So he tailors song choices to whatever the patrons might be going through. Having a fight with your boyfriend? A little Pat Benatar is perfect, he says. But one night at the usually jubilant, yet peaceful Tin Pan Alley a drunk patron needed to be escorted out by the police. What do you sing when four cops are arresting someone only a few feet away? In this case Lady Gaga’s “You and I” seemed appropriate to distract from the drunken elephant in the room. When he sang it again for a new audience later in the same gig he let them know that the last time he performed it someone got arrested. It’s all about the mixtape, be it on stage or in life. There’s a song for every scenario and it’s what informs his show Mixtape.

“I’m of a certain age where I loved to make mixtapes in the 1980s and 1990s,” says Jackson. “I’d make them for friends. You know, like when a girl’s boyfriend who you know is gay anyway breaks up with her, you make her a mixtape to make her feel better. I still do that with the music at dinner parties, set the soundtrack. My therapist would say I have control issues. It’s always been my thing, though, setting a soundtrack for life.”

Jackson lets out a sigh when thinking about his work, which like for the rest of the world was interrupted by the pandemic. At the end of 2019 Jackson appeared in the off-Broadway musical A Strange Loop, for which he won an Obie Award and the play won the Pulitzer Prize for Drama. But then it all seemingly vanished. Plans to take it to Broadway as well as the award ceremonies that usually come with such accolades all disappeared. Working as an actor for over 20 years this felt special. And then it was gone. Rehearsals have begun again and there are plans for a run in Washington, DC, with hopes to go to Broadway thereafter. All the uncertainty still reigns supreme, says Jackson. He’s hopeful, but weary. And with Mixtape he hopes to connect with us all through music to ease our minds, shed trauma, and prepare for joy.

“It’s about getting art out,” says Jackson. “The most helpful thing you can do is tell the truth. That’s what I do with my shows. I tell the truth through music and humor. We all work things out differently. I just prefer to do it in front of an audience.”

James Jackson, Jr. presents Mixtape at the Post Office Cabaret, 303 Commercial St., Friday, October 1 and Saturday, October 2 at 9 p.m. Tickets ($35) are available at the box office and online at For more information call 508.487.0006.

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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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