This week Playbill catches up with James Jackson, Jr., who is currently making his Broadway debut as Thought 2 in the Tony-winning Best Musical A Strange Loop, after receiving an Obie Award for his work in the musical's Off-Broadway premiere.

The actor, who has performed at Joe’s Pub, Green Room 42, DROM, 54 Below, A.R.T.’s Club Oberon, Los Angeles’ Lyric Theatre, and Provincetown’s Tin Pan Alley, has also been seen in the Radio City Christmas Spectacular and the national tour of Whistle Down the Wind as well as productions of Dreamgirls, Henri Gabler, and The Wild Party.

Checking In With… Hadestown Star Soara-Joye Ross

What is your typical day like now?
It features a lot of stretching. It features a great deal of Joni Mitchell, Lizz Wright, Tori Amos, and Kathleen Battle. It’s built on the foundation of a secure relationship with my neti pot. There are skincare products. There’s a gym that I’m becoming better friends with. And, there is a heavy rotation of salads from Chop’t, the burger at The Lambs Club, and the naan bread from Deep.

Are there any parts of your roles or the musical that seem particularly poignant/relevant following the events of the past two years?
I don’t think there’s a particular part of the show. It’s more about the entire event itself. Our story is not typically a story that is told on Broadway. I enjoy people-watching. I think people see the umbrella marketing of our show “The Big Black & Queer-Ass American Broadway Show,” and they think “Oh, this might not be for me, but I’m going to support it and see what it’s about.” Some people are surprised to see themselves reflected in the show. We all have a family. We all have career aspirations. We all have been on a bad date. My favorite thing each night is people-watching. Watching people receive this show is purely magical. Watching people receive something they didn’t think was for them is something I thoroughly enjoy.

What does it mean to you to be making your Broadway debut in this particular show? What did you feel the first time you stepped onto the stage at the Lyceum?
Everything feels pretty great. I’m pinching myself daily…still. Stepping onto the stage at the Lyceum for the first time was pretty cathartic. Everything made sense. This journey has been very long. Patience feels like a tangible thing. I have wanted this for so long, and with this particular show it is so very special. In my 20 years in New York as an artist, this is one of the very few creative spaces where I was allowed to bring my entire self into the room. If a writer, collaborator, or creative team (or anyone for that matter) ever asks you to come as you are, always go there.

Can you share one or two memories about Tony night?
The morning of the dress rehearsal was my “can’t believe what is happening” moment. We got off our bus and walked into Radio City Music Hall as the cast of Company was leaving. We waved and exchanged pleasantries in the lobby. I walked through the orchestra of Radio City and was greeted by a group of the amazing ushers who work there. A decade ago I was a singer in the Christmas Spectacular, and they were cheering me on. They knew how far the journey had been. Backstage, while they were putting microphones on us, I saw that Girl From the North Country was performing onstage. I watched on the monitor backstage, and I said out loud, “Wow, Mare Winningham is amazing!” At that very moment, I got a tap on my shoulder, and as I turned around to discover that it was Anthony Edwards, he looked at the monitor and said, “She’s pretty great. Someone oughta marry her!” I don’t get starstruck, but this was starting to be too much. I took two steps back because I was in shock, and I bumped into something. I looked over my other shoulder and didn’t see anything. Something in my head said I should probably look down. And there she was. I had literally bumped into Bernadette Peters. The Bernadette Peters. I knew then and there I was going to gay hell, and I’d never work in this town again. She looked up and said, “Hello. I can’t wait to see your show.” I don’t know if I had words. I mustered up a “Love your dress.” I think she said, “It’s Zac Posen,” and she asked, “Would you like to take a picture?” My stage manager Cherie B. Tay was there with the camera, and later told me the moment looked like “little eight-year-old James had just met his Broadway fairy godmother for the first time.” That I will never forget. 

The night of Tonys? I remember two things…. Sitting in the audience directly behind Jonathan Groff while I was eating jelly beans out of a borrowed clutch (thank you, Barbara Whitman), and then running to the stage like a track star when they called our show for Best Musical.

During this time of reflection and re-education regarding BIPOC artists and artistry, particularly in the theatre, what do you want people (those in power, fellow artists, audiences) to be aware of? What do you want them to consider further?
I am a Black gay man. I have so many stories, and complexities, and so much history. I am as interested in those stories, complexities, and histories as I have been in yours.

What, if anything did you learn about yourself during the past year-and-a-half that you didn’t already know?
There is no greater joy than creating something from scratch and giving it to someone. I started sewing during the pandemic. Can you tell?

Do you have any other stage or screen projects in the works?
I’m returning to the small stage by myself for the first time in a long time. I’ll be doing a solo show called Here for the Night at The Green Room 42 on Monday, November 7th at 9:30 PM.

What organization would you recommend people learn more about or donate to during this time of change?
The Center for Black Equity.

Checking In With… Frozen Tour Star Caroline Bowman

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