15 Questions in 15 Minutes with ‘A Strange Loop’ star James Jackson, Jr.

The one and “onliest” James Jackson, Jr. is a New York City-based actor, performance artist, Kabarettist, vocal coach, producer, and everything else a fabulous entertainer should be. From the downtown arts scene and regional theater to the grand stages of Radio City Music Hall and Carnegie Hall, the intimate cabaret spaces of 54 Below, Joe’s Pub, and The Green Room 42, and the phenomenal Off-Broadway production of the 2020 Pulitzer Prize-winning musical A Strange Loop at Playwrights Horizons (in the role of Thought 2), Jackson’s 20-year career has racked up 15 minutes after 15 minutes after another 15 minutes of fame. And there’s nothing strange about that loop; with so much talent, graciousness, and wit, it’s completely expected and richly deserved.

James Jackson, Jr. Photo by L Morgan Lee.

Jackson has continued to be active during the current pandemic shutdown, playing the central character in the upcoming theatrical song cycle Different Stars: A Reckoning with Time, Trauma and Circumstance by Karl Saint Lucy,  which examines the haunting memories that emerge, while alone in quarantine, of a first queer love gone awry. The new livestream presentation on YouTube will have its world premiere on Saturday, August 15, at 7:00 pm, as a benefit for QORDS – a music camp for LGBTQIA+ youth (ages 12-17) in North Carolina.

James generously agreed to share some time with us to take our Pop quiz about the shows and their themes, personal career favorites, and the significance of love and fame.

  1. Are you satisfied with the way you’ve been spending your time in quarantine?

James: Satisfied isn’t a word that’s come up during this. It’s been more about “What can I do for the next few hours, days, minutes?” while also understanding that there is no due date anymore. None of us “have” to do anything right now. So, I read a few pages of that book. I try a few of those new recipes. One thing I’ve been doing is making pants. Pants and caftans. I’ve been sewing. A lot. Sometimes all day. It’s so peaceful and so unbelievably cathartic and rewarding to make something from absolute scratch, laid out in the middle of my quarantined apartment, and then send it off to someone else in the hopes that it brings them some joy. I even put all my sewing stuff on an Instagram page to sort of document it. If it wasn’t hash-tagged, did it really even happen? Check out @sewsumthinelse.

  1. Have you ever rediscovered a personal memento that brought back a flood of emotional memories?

I’ve been saying “I miss my jewelry” during the pandemic. It may seem superficial, but we are all a little bit “that person.” Most recently, I miss a ring, or a bracelet, or a certain pair of jeans . . . or Oh, God, a swacket (combination sweater/jacket). I miss them because they remind me of the occasions on which I would have worn them, which means people would’ve been there and I desperately miss being around people.

  1. How would you define love?

It’s the thing that makes your shoulders go down. Let me explain. I stopped performing for a bit several years ago, went back to school, and became a massage therapist. I worked in a spa for many years after that. I studied the body for a very long time. I learned a lot about that perfect state of relaxation. When you see a skeleton in a biology class, the clavicles are almost a complete straight line. That’s the state you’re trying to get a body to achieve. Do it now. Let your shoulders relax and try to envision your clavicle as one straight line. It’s so relaxing, right? Letting your fingers just freely wiggle, your arms have no tension – it’s our natural state. When you walk into certain spaces, taste different foods, experience different people, see that perfect sunset or something like that – what do your shoulders do? If you encounter someone and they make your shoulders go down, stay there. That’s love.

James Jackson, Jr. (left) and the cast of Different Stars (Victoria Huston-Elem, Danielle Buonaiuto, and Karl Saint Lucy). Photo courtesy of the production.
  1. What’s the best advice you’ve ever been given by a friend?

Sing it like you got the job. A lot of working as a performer is about getting that next “gig” or hunting for that “track” where you may fit in. A lot of performers can be great mimics – and there’s definitely a market for that. Following direction and “taking the note” are tremendous assets. But remembering to be yourself is the greatest power of all. Remember that they hired YOU! I used to get nervous in a role and would want to perform it like I thought they wanted it done – if that makes sense. Trying so desperately to be what you think some casting person or director or producer wants you to be is definitely a balancing act. But to take a song or a role and “sing it like you got the job” is the best advice anyone has ever given me.

  1. What was your reaction when you first found out that the show you were in last season won the Pulitzer Prize?

My jaw dropped. I cried. And then (and still) I just wished all of us could be in a room together hugging and screaming and crying and doing the Electric Slide.

  1. What one line or lyric in A Strange Loop could you relate to most?

“I’m stuck with who I am/Someone who’s self-perception is based upon a lie/Someone who’s only problem is with the pronoun ‘I’” – it’s in the final song of A Strange Loop, and it hits me the hardest every time I hear it. I have spent, still occasionally spend, and probably will always spend (to some degree) a great deal of time dealing with my feelings around the worth of “me” or “I.” There’s a lot to unpack there, and I try to work on it. Is it growing up queer in a 1980s world that doesn’t recognize me in the way I seemed to be discovering myself? Is it what happens from balancing, asserting, and relishing in my Blackness in that same 1980s Boston, Massachusetts, that may have looked at me as out of place? It took a long time to realize that much of my struggling “I” was based on what I perceived “they” were seeing. Choosing a career looking at human behavior and replicating it, while also hoping you “get the part,” can be a mind trip . . . if you let it.

James Jackson, Jr. (left) and the cast of A Strange Loop. Photo by Joan Marcus.
  1. Have you ever heard voices in your head questioning your choices?

There’s been an ongoing staff meeting in my head for years. I’m human. I’m reading the minutes of last week’s meeting while I’m answering this.

  1. What’s your first creative memory?

I used to put on shows in the living room for my family, and I would just tell jokes, and maybe play the piano. My jokes were stolen from either Fozzie Bear (because The Muppets are the truth) or from Redd Foxx (because access to my dad’s 8-tracks can help shape a child’s imagination in the best way).

  1. Who was the biggest inspiration in your career?

My mother. When I was very young, I was so envious of her being able to play the piano.  So, she taught me. She was a bit of a musical prodigy when she was a kid. She also taught me about rhythm and cadence and how to tell a story. She first taught me music by letting me turn pages for her while she played at different family functions, weddings, funerals. I realized the musician was really in charge of setting the tone. We memorized Paul Laurence Dunbar and Countee Cullen poems together. Oh, and she taught me how to cook.

James Jackson, Jr. Photo by L Morgan Lee.
  1. Which three songs do you most enjoy performing?

“Do I Move You” by Nina Simone; “What Would I Do Without You” by Ray Charles; and “You Turn Me On” by Labelle (but only if I get to sing it with LaDonna Burns).

  1. What one line in your cabaret act is always guaranteed to get a laugh?

I try to keep the stories and jokes fresh as best I can. I do love an awkward silence though. As a kid I watched Whoopi Goldberg’s one woman show until I wore a hole in the VCR tape. She played a character named Fontaine visiting the Anne Frank house in one of her shows. I remember thinking as a child about the predominantly Jewish neighborhood (in Boston, of all places) that I grew up in, and how that shaped much of my humor. In the end of her diary, Anne Frank talks about being split into two as a person and still being able to see all the joy in life – balancing cheerfulness and flippancy. I remember wanting to create a quieter moment in the last solo show I did. It was right before I planned to tell a story about the last few weeks of my mother’s life and her four-year battle with cancer. I brought the lights down and said “We’re about to have a very serious moment. If I could have everyone’s attention, please. As my dear friend, Anne Frank, once said . . . ’Sshhh.’” It took a minute. But it worked.

  1. What has been the most memorable experience in your career to date?

Every single millisecond of A Strange Loop.

James Jackson, Jr. Photo by Brian Edwards.
  1. What do you miss most about being in front of a live audience?

Forgetting things and making them work. Hearing people laugh. Hearing people breathe is beautiful. Hearing an entire room go silent, but because they’re listening. Hearing people synch up is like tangible magic.

  1. How would you describe yourself to people who don’t know you?

James is great at parties. James is good with a map. James should bring the potato salad.

  1. What’s the best thing about achieving fame?

I hope I never have to find out.

James Jackson, Jr. Photo by L Morgan Lee.

Many thanks, James, for an extended and enlightening 15 minutes! Congratulations on your extraordinary success in A Strange Loop; may your Different Stars sparkle and your fame continue to flourish!

Different Stars premieres on Saturday, August 15, at 7 pm, livestreaming on YouTube. To view, go online, or click on the arrow below:


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