From us: We’ve never met Aisha Jackson in person, we just admire her with all of our might. When we had a friend offer us her email address to see if she was interested in being on the blog, we couldn’t help ourselves. Since coming to NYC in 2013, she’s performed on Broadway, Off-Broadway, and regionally. Her Broadway credits include Beautiful: The Carole King Musical, Waitress, and being the first woman of color to perform Anna in Frozen on Broadway. That princess look suits her. She was in rehearsals playing Snow White in Britney Spears’ new Chicago and Broadway bound musical Once Upon a One More Time when COVID-19 shut down the industry. You can understand why we might not think Aisha had time for our little blog.

But, as we came to learn, that’s not who Aisha is. She is gracious with a capital “G”. Her written word is infectiously inspiring, her heart is pure gold, and talent to send you through the rafters. When we imagine what the rebuilt world of theatre looks like, you imagine someone like Aisha leading the way. And we have proof:

She recently participated in #TheaterInColor’s IG video thread revealing her reality as a POC in Theatre, particularly in reference to experience as a standby for Anna in Frozen. And we know the challenge must have been real, because we naively perpetuated that reality. In our original form we sent Aisha pre-Coronavirus, we asked, “what it felt like to play a role she wouldn’t ‘traditionally’ have had the opportunity to play.” 

Even though she had never met us, Aisha graciously omitted the question, answered every other question in breathtaking form, and wrote back explaining why that wording was offensive. That’s grace. In the “Moving Forward” section of her #TheaterInColor post, she challenged storytellers to cast BIPOC artists in the principal roles. Complicated, varied, and 3-Dimensional roles that they’re not only capable of, that they deserve. Above that, show the audience you know that they deserve them. Don’t give them the cover. Give them the role. 

We hope you enjoy Aisha’s wisdom for The Obvious Path- both from the normal of old and the world we’re hoping to reimagine. We’re thrilled you get to experience something that has been so meaningful for us. And, just for the record, if The Obvious Path was a musical: We’re casting Aisha as the lead.

Aisha Jackson. Wow, What an honor it is to have you featured on our blog. Can you please introduce yourself to our readers?

Hey there! Thanks for having me! I’ve lived in New York for six years now, but I am originally from College Park, Georgia. I grew up singing and dancing with my family in church, and I have always had a passion for the arts. After graduating college in 2013, I moved to New York to pursue my dream of performing on Broadway! I had no money, no place to live, and no job lined up. What I did have was about five bags and a lot of faith!! Since moving here in 2013, I’ve done three Broadway shows and have been blessed to have a myriad of opportunities to do what I love. Truly grateful!! 

You went to University of Northern Colorado. What brought you to school there? Positive or negative, how did UNC impact your career?

 When I was a junior in high school, I participated in the main stage production of Hairspray at the International Thespian Festival in Nebraska. Since UNC was the hosting school that year, we rehearsed for weekends at a time on campus. When making my decision for college, I remembered my time at UNC being joyful and welcoming. So, I gave Colorado a try, and I loved it! I never fell in love with the snow though. It’s pretty to look at, but those treks across campus in the snow were no joke! 

I think every college has positives and negatives. It’s definitely what you make it! I am grateful for the lessons I learned at UNC! I felt like I received a well balanced education, and I had my very first voice lesson. I grew tremendously during my years there, and I carry those lessons with me still today. I do believe all college curriculums could stand to be updated. There are countless career opportunities in this industry beyond the stage that aren’t offered as fields of study at most schools. I also believe we need more college professors of color and more teachers and/or guest artists that have worked in the industry. 

What was the most important thing you learned your first few years out of school? 

DO NOT COMPARE YOUR JOURNEY TO OTHERS! There are countless paths to achieving the dream of performing on Broadway. Comparing your path to someone else’s will not help you get there any quicker. We all have unique gifts that only we can bring to the table. I had to trust what I brought to the table and believe that my time to shine would come in due season. 

How do you handle the pressure and rejection this business inevitably brings you?

WOOF! There is a ton of rejection involved in this industry. I think it’s important to have a strong love and passion for performing. Otherwise, you’ll fizzle out during the times of rejection. My remedy is remembering that I want to inspire others by utilizing the gifts God has placed inside of me. I can’t give up if I desire to see that become a reality. I also realized that not booking a job doesn’t mean I suck. Maybe they wanted someone taller or maybe I just wasn’t right for it. Who knows? At the end of the day, I’m still a great performer and my blessing will come when it’s supposed to. What is for me will not pass me by. 

And now the question we ALL want to hear about. At the time of this interview, you are the stand by for Anna in Frozen on Broadway and are the first person of color to portray her. Can you talk us through this journey? Give us all the feelings!

That I am! Stepping into the role of Anna has been a whirlwind. As a standby, which is an offstage cover for a principal role, you don’t really rehearse on your feet until the week after the show officially opens. Swings and standbys report to rehearsal everyday but we are mostly on the sidelines taking copious notes. The main focus is on the cast that will be on every night. 

I was told I would be going on for Anna the day BEFORE the first understudy rehearsal. YEP! Day BEFORE! Thankfully, I had done my homework and was as prepared as I could be. (Plus, we’d already done a full production of Frozen in Denver. I’d rehearsed the Denver version, but the Broadway version was a bit different.) I said prayer, took a deep breath, and trusted my instincts. With help from the dance captain, the ensemble, our wonderful wardrobe team, our magnificent stage management team, and GOD, I stepped onstage and made it happen. On March 28, 2018, I took my very first bow as a principal on Broadway!! I also became the first woman of color to portray Anna on Broadway. (There were already women of color playing the role in the parks.)

Anna has been such a wonderful role to play! She is goofy, unique, quirky, loving, speaks her mind, and is unapologetically herself. Anna and I are alike in many ways, but she’s taught me how to embrace my weirdness more and more! Playing the role of Anna also made me realize how important it is for young men and women of color to see themselves represented onstage. It’s been a pleasure to step into this role and show them that they too can play princesses and princes. My fondest memory from the first week I went on was a woman telling me she overheard a young African American girl in the audience say, “Mommy, she looks like me!” Hearing those words reminded me that it wasn’t about me; it was, and still is, about what God wants to do through me. I’m grateful for the chance to show these beautiful chocolate drops that their possibilities are limitless!! 

How do you define success in this industry?

If I am doing what I love, I am succeeding. Whether it be on a Broadway stage, at an open mic night, or volunteering for career day, I am doing what I love. Success to me is being true to myself, showing up and doing the work, using my gifts to inspire and bring joy, standing up against inequality, and breaking down barriers! Success is what YOU make it! 

Where are you on your mountain?

In the middle somewhere! I never really want to be at the top of my mountain because I feel like there is always more to learn, more to do! I do know I’d like to start a mentorship program for women of color. I am also dreaming of someone writing a show/role just for me. Maybe I’ll do it myself! Who knows?! I do know one thing though! My next Broadway show is happening in a few months! SUPER EXCITED!! 

How has Coronavirus changed your perspective on the business and/or your life?  

This pandemic has actually gifted me with time to connect more with God, my family, and friends. I carve out time daily to pray, worship, meditate, read my bible, and FaceTime my friends and family. Being stuck at home has forced me to find peace and joy in new ways, and it's given me time to develop ideas that I’ve put off. I have wanted to start my own mentorship program for quite some time. So, I’m using this time to connect with young artists and answer their questions about the industry. Broadway is currently shut down, but when it returns I want them to be prepared. I’ve also challenged myself to find more ways to be active in the fight against racism and prejudice that is still very much so alive in our country. And I have been extending grace to myself and to others. We must remember to be kind to ourselves during this strange time. I challenge myself daily to focus on what I DO have and switch my perspective to gratitude. It’s not always an easy shift to make, but it is very beneficial for my mental, spiritual, and emotional health. 

RAPID FIRE:

Favorite Broadway show: It’s a tie between Aida and Memphis! 

TV show you binge: How to Get Away with Murder, Grace and Frankie, Queen Sugar, Handmaid’s Tale

On your commute, I’m listening to ________: Jonathan McReynolds, Emily King, John Legend, Gregory Porter, Lianna Le Havas, Tiana Major9

Religious, Spiritual, or nah?: I have a beautiful relationship with God! 

Former side hustles: Hosting at Jane Restaurant 

One tip for auditioning?: Think of auditioning as an opportunity to do what you love!! Also keep an audition log. Write down who was in the room, what you wore, how you felt about it, what went amazingly well, and how you can improve next time. 

Any bad audition stories?: Uh….I’ve had someone answer a phone call while I was singing for them…

Your first experience performing was _________ : Performing period? In church with my family. Performing in a musical? Once On This island in the sixth grade!

I get inspired when _________: I see young people get excited about the arts. It always reminds me that we have to pave the way for those coming up after us. 

Nobody is talking about _______, but it’s so important because ___________: Police brutality against people of color, but it’s important because it’s inhumane, unacceptable, and could happen to any of us. 

Job you didn’t expect to book: Standby for Anna because my first audition for Frozen was for Elsa! 

Biggest beef with the business: Lack of representation and inclusivity on and off stage 

Favorite thing about the business: Connecting with the audience after the show! The power that theatre has to change people and open their minds.  

Social media handles?: Instagram: @gifted2sing Twitter: @starringaisha (My siblings made my twitter page for me…I should change that name soon) 

Anything you’d like to promote?: Be on the lookout for my mentorship program. Challenging myself to start one this year for young women of color to connect with other women of color succeeding in their industry. I want to show them that they’re possibilities are limitless! 

Photo Credits: Photo 6 and 7: Janie Willison

From Kat: I had the pleasure of getting to know Alex while I was working at DDO Artists in the Voiceover department. He has one of those 'voices' that you can't forget. He then made the leap over into our commercial department right around the same time I switched divisions as well. I actually think Alex booked his first commercial audition, which is not surprising when you see this guy perform. If you saw Dave Malloy's Octet this past year, you know what I'm talking about. He's as kind as he is talented, and as joyful offstage as he is on. 

Getting to hear about Alex's journey was such a joy. He is honest, vulnerable, insightful and offers a surprising look at what it takes for talent, even if they're on Broadway, to get representation. He has a lot of gems of wisdom in here, so I'll let him take it from here.

Alex! One of my favorite clients EVER who had a bit of a hard time recognizing me after a show! (*Insert crying laughing face emoji here*) Can you please introduce yourself to our readers?

Hi, I’m Alex Gibson! I’m an actor, improvisor, and occasional writer. I’ve been in the city for a bit now and went to school at NYU. I was in Natasha Pierre and the Great Comet of 1812, SpongeBob SquarePants: The Broadway Musical, and this past summer I was in Octet at the Signature Theatre. Andddd that’s me!

You attended NYU and were in the inaugural class of the Tisch School of the Arts’ New Studio on Broadway. How did you end up there? Can you talk to us about how/if the program set you up for the career?

It was crazy being in the inaugural class because we became the guinea pigs for everything they were developing! In hindsight, it was one of the most amazing opportunities I could have had because they were so willing to try so many different things. We got an incredible amount amount of masterclasses and opportunities that I wouldn’t have had without the program. Something else that was amazing about this program was that they treated us seriously as actors and as individuals. It’s pretty groundbreaking when you are eighteen, in a new environment just trying to figure out where you fit in the mold, and then you find out that there is no mold! They didn’t want me to ‘fit’ any type of mold, and that was life changing. They gave me permission to be an actor first, and tell a unique and powerful story on my own. Very grateful for that program.

I actually did not showcase out of school. At that time, NYU didn’t have an official showcase, so we had various productions that industry folks would come to instead of a showcase.

We had the pleasure of seeing you perform in Octet at The Signature (so good y’all). What is it like to have a part written FOR you? Can you talk to us about that rehearsal process and what is was like harmonizing every night together? 

Ah! I love Octet. I am in love with Dave Malloy (Writer and Composer) and Annie Tippe (Director). They are both thoughtful and down to earth people, so getting to be in that environment was such a dream for what the creative process should be like. It was incredible on a number of reasons. One, being that Dave has a gift for writing for voices that are not his own and really delves into what those voices are. He wrote a real bass part! So many composers write for their own voice and what fits comfortably for them. So, to get to be in a show where I was singing in such a comfortable range for myself and at the same time, getting to be funny was such a gift. So many bass parts usually just feature a ‘basso profondo’ speaking voice, but in this show it was so freeing to be able to be both. 

There were two workshops, which I luckily got to be involved in those which was helpful to get to work on the music. The music is so incredibly dense and I definitely had some ‘brain melting out of my ears’ moments! But, he is such a smart writer, once I heard what the song was as a whole, it just clicked. I understood how it worked, and it just stuck. We had three weeks of rehearsals for the production, so we had to be so specific with working. We were incredibly lucky to have the Music Director, Or Matias, who is one of my favorite music directors to ever work with. He is a genius and would be able to dissect incredibly difficult music and pick out one little part that was off in the entire 8 staff sheet music. We owe so much of the quickness and accuracy to him. It was my first time working at the Signature too, which exceeded my expectations. They created such a great environment for everyone involved and it was such a beautiful space for the creative process to take place. It was really special. 

How did you find your current representation? (If my memory serves correct, you were in SpongeBob before you found your current rep right?) Can you talk us through that timeline if you don’t mind? We love agent/manager stories!

So... it's not immediately great for the hope aspect haha but here we go. I had gotten Spongebob out of an EPA and was actively looking for representation at that point. I was sending out postcards, going to "pay for plays" - you name it I did it. And nothing was quite working. So when I knew I was going on for Squidward I bought tickets and would offer agents free tickets to come see me perform. And even then I had a great deal of difficulty getting people to come. Which at the time felt crazy given how many times I had heard to just let people know when I was finally in something they could come see!  But ultimately, it's a good reminder to not beat yourself up - agents are just busy! They aren't going to be able to come to every random show they get invited to. I have to check myself on this all the time, but theater is - at it's best - about creating and perpetuating empathy, compassion, and imagination. It's surprising how frequently we forget that agents and other industry folks are people too! They have lives and busy schedules and all that.  We are all just people working together to try and make stuff happen.

This story does get better tho! I have a friend who was able to get me a meeting with reps who I auditioned for and then signed with. They are amazing and it happened to come at the perfect time where I really knew I needed an agent. I had been going it by myself for a bit but at that point I really needed someone to help me have the sometimes difficult conversations with casting offices and navigate some of the stuff that was coming my way. So it was a long journey but I'm incredibly happy with where I've ended up!

You are SUPER versatile and have been on Broadway, worked at some wonderful regional houses, performed in celebrity concerts, done voiceovers, commercials and have taken tons of classes at UCB. Looking back to your first year out of school, what is the most important thing you did that help set you up for success? If you could go back and change something from that first year, would you? If so, what would that be?

I had a moment of fierceness, that I try to remind myself that this actually happened…. but I did My Fair Lady at The Guthrie, and it was such an incredible experience. I loved working with this theatre and really wanted to try and go back whenever I could. I saw that they were doing A Midsummer Night's Dream, and I really wanted to be considered, but knew it was a long shot since they had really only seen me sing and dance for My Fair Lady. SO...I  reached out directly to the artistic director and explained that he had only really seen me sing and dance, but that I was trained in Shakespeare and asked for an audition. Turns out he gave me a shot, and I booked it! 

When looking back, that is sooo out of character for me, but I am really proud that I took that leap. Of course, I only recommend this when you are really right for something and your skill set fits perfectly. Confidence is at it’s best when it is the result of a cultivated sense of self and experience. 

If I could change one thing, it would be how I handled a tour I did in Japan during my first year out of school. I was so worried about what was next in my career and about what I was missing in NY. Looking back, I wish I could have chilled out and realized how cool it was that I was in Japan!

What’s been the biggest surprise of this industry? 

When looking back at the history of show business, I am constantly reminded that this has all happened before! It’s kind of freeing to think about. I think about this with just how quickly things happen in this industry. Amazing things and devastating things. Shows open and close. Shows sometimes go to Broadway and many times they don’t.  So, at the end of the day, its freeing to know that I’m not the first person to experience all of these things- good or bad. We have all had the rug pulled out from under us, and that’s comforting to know in those times.

Has there ever been a moment where you felt like giving up or that this career wasn’t for you? If so, what did you do to get through that time?

Constantly. All the time. BUT I think it’s healthy to engage with that lightly. Therapy. Therapy. Therapy. For me, I try and think about why I got into this in the first place and try and work out if those same reasons are still serving me or helping me in the way I thought they would. At this point, I feel very lucky that I get to make a living doing this and that I have a group of collaborators that I enjoy working with. At the same time having in the back of my head that this is my job and it doesn’t need to be something that makes or breaks my existence.

Where are you on your mountain?

Right now, I am in a rocky mountain spot! I think career wise, I feel excited and that I am getting to work with incredible collaborators and feel like I am moving in the right direction. Personally, I feel like I am in the midst of figuring out a lot of stuff that has been confusing and very complicated. So when you put them together, I think I am moving up, but all I can do right now is  focus on the little rocky parts right in front of me.

RAPID FIRE:

Favorite Broadway show: Sunday in the Park With George

Three pieces of advice to 13 y/o Alex?: Start meditation and work on stress reduction, take ballet now, and you don’t need everyone to like you all the time to be worthy.

TV show you binge: Big Mouth

Podcasts you love: Las Culturistas (college buddies of mine!)

Religious, Spiritual, or nah?: Spiritual (ish)

Former side hustles: In college I graded papers in the computer science department.

Biggest tip for auditioning?: Wear something that you would feel cute in on a date!

Fav SpongeBob character?: SpongeBob...sorry if that is lame! 

Any bad audition stories?: omg all of them. So many. I used to have a habit of forgetting words, but I wouldn’t stop singing. So, one time I sang ‘You’re a Mean One Mr. Grinch’ which is all ‘seussisms’. So I forgot all the words and decided to start making up the lyrics. I ‘improv'ed’ the entire song. It was not okay. Shockingly, I did not book it!

Favorite audition song: Folsom Prison Blues, by Johnny Cash

What inspires you in 2-5 words?: Those before and yet to come.

Job you didn’t expect to book: SpongeBob

Biggest beef with the business: That so many theatres are dusty and moldy. So, if it’s an old theatre, you are sick all the time! It’s completely at odds with being able to perform well.

Social media handles?: @alexgibby on IG and Twitter

Anything you’d like to promote?: I’ll be doing The Unsinkable Molly Brown! Come see it!

From Kat: Here’s the funny thing about Jessie… I can’t remember meeting her! (She will read this and instantly remember because she is just that kind of person). We probably met at an audition? Regardless, in a funny way, she just feels like one of those people I’ve always known. This positive, joyful, talented, successful and humble presence in my circle of NY people. She is as real as they come, my friends. I got to follow her career through social media, Peter met Jessie when she was doing “Freaky Friday” at Cleveland Play House, and we’ve stayed in touch personally and professionally when I got back to NYC.

If that weren’t enough, when I started at HCKR I noticed a familiar name on my new roster….THE Gilbert L. Bailey II! I was thrilled I get to work with one of the Bailey’s. They aren’t just sickly talented, they’re also some of the hardest workers I have come by in this industry. They have a beautiful relationship (which you will hear about more) and are good to the core. Enjoy this honest, joyful, and humble feature. 

Jessie and Gilbert! We are SO excited for you to be our first couple interview (cue studio audience: “awwwww”)! Can you introduce yourselves to our readers? 

Jessie: YAY I’m soooo excited to get to do anything couple-y :) I’m Jessie Hooker-Bailey! I was most recently in Waitress the musical on Broadway, which just closed up on January 5th! I’m from Wilkes- Barre, PA. I love wine and cheese, good friends and my husband and our future dog (wherever you are and whenever Gil lets us get you ;) ) 

Gil: Hey, I’m Gilbert! I’m currently in the cast of Beetlejuice on Broadway and I am happily married to Jessie! 

Jessie, you went to Shenandoah and Gilbert to Penn State. Can you talk to us about how/if those programs led you to NYC and how they impacted your career? Did it help find your representation? 

Jessie: I went to Shenandoah Conservatory in Virginia. Looking back and now having a little bit of real-life/business experience I’m especially grateful for Shenandoah’s music training. I graduated with a BFA in musical theater but at the time I studied we had to take music theory with the music majors. I had to compose my own pieces and all of that. Not saying I’m a mastermind now, but I’m a decent sight-reader and I love learning new melodies and harmonies. I think those skills help me when it comes to working on new musicals and workshops of new shows. I feel super prepared and well versed in that area specifically thanks to Shenandoah. Representation? Nah- I kinda had to find all of that stuff on my own and in classes once I was here in NYC. 

Gil: Penn State was really hitting its stride as a top training program when I was attending so I feel I was unwittingly lucky to have ended up there because I really knew nothing about Music Theatre college programs when I applied. I was planning on going to school to be a lawyer and only considered performance as a possibility of study after one of my high school drama club directors suggested it in my junior year. Because of her suggestion, I did a summer program at University of the Arts in Philadelphia between my Junior and Senior year that was supposed to give you a sense of what college was like. The summer was fun enough, so that fall I decided that I would throw my hat in the ring at a few auditions and see what came of it. If I got in, cool, and if I didn’t, that would be cool too because I was a Mock Trial captain and truly was interested in Law as a profession. I did well and got into several programs, but getting into The Penn State Music Theatre program was one of the best things that has ever happened to me in my life (fun fact: I only auditioned for Penn State in the first place because of a joke that Carlton tells in a episode of The Fresh Prince of Bel - Air. He called it the “state pen” and that’s what I recognized the school from. As I said, I didn’t know anything about music theatre programs!). Penn State provided me with a lot of wonderful things, the most important of which, I would say, is confidence. When I was there, so many opportunities existed and I felt it easy to be inspired by not only the students in my program, but most importantly, the students outside of the program who represented a broad variety of demographics. These were the young versions of audiences I would be hoping to entertain professionally in the future. Going to a program like Penn State’s program, which is as intimate as a conservatory but within a hugely populated university, really mirrored what it is actually like to live in New York City as an artist. We were on Penn State's main campus and had less than 60 students total in all four years while the campus as a whole represented student body of 48,000 or so. That’s what it’s like to be a member of a performance union (AEA) that has about 50,000 members in total while working on an island that holds 8 million people. It was really good preparation for days that the denizens of the New York City subway don’t care to be quiet so you can get some last-minute study in on your lines on the way to an audition. When it was time to graduate I wasn’t convinced I would move to New York but Penn State changed my mind again because I got an agent from showcase and booked a NYMF show soon after. I would say Penn State provided me a great springboard into the world of professional music theatre. I had no context before I started the program but I can truly say that where I am at this point in my career is the result of the four years I spent studying there. 

You both have really found your footing here in NY. With that, came tons of hard work and traveling. Can you talk to us about working out of town and/or doing long distance? 

Jessie: Yeahhhh. We met doing a show which was super special (I was Squeak and he was Harpo in The Color Purple at Milwaukee Rep). After that, we came back to NYC and he went back on the road and then eventually to Broadway with Book of Mormon, and I went back to my babysitting and catering gigs. It was definitely one of the most testing parts of our relationship in the beginning. I was so in my head about the fact that he was on Broadway and dealing with what being on Broadway means (8 shows a week, etc) and I was unhappy in my side jobs. I can, with full transparency, say I was resentful because I didn’t yet understand what Broadway was (in reality). It was, to me, a dream I had been working toward and hadn’t gotten yet and was upset with myself because of it- so that made it hard at times when Gil wanted to come home and decompress from a day that isn’t always rainbows and butterflies. We worked through it but it’s SO REAL that it was hard. I was getting work that was out of town which brought its own issues but I’m not even kidding, Gil has been a trooper because he simply just understood I had to go out of town for work. I found out I got “Freaky Friday” just days after he proposed and we planned most of our wedding when I was on the road (in California, Ohio, Texas..). He did all of the venue shopping with the help of my bestie Jill, met with vendors.. it was incredible. He just has my back in a lot of ways and I think he handled it better than I would’ve if it were me at home and him away. He taught me a lot about being a good partner in that way. 

Gil: Well that was a nice little admission from Jessie because some of those times were indeed tough. Long-distance takes a lot of communication and understanding to do well and we were kinda thrust into long-distance situations so early in our relationship that there really wasn’t any way to expect us to handle it better than we did. Undoubtedly the communication between us would go a lot smoother were one of us to go on tour or take an out of town gig now. That being said, in my experience going out of town can be a trick bag. Some of my most fulfilling theatrical experiences have occurred out of town, like meeting and working with Jessie, the woman who would end up my wife, in a production of The Color Purple, in Milwaukee, or getting to play Ozie Powell the LA production of The Scottsboro Boys. On the other hand, my time on the international tour of Riverdance proved to be so traumatizing that I have literally never looked at a pair of tap shoes the same way since. I think there are people who love to be on tour and love to be working out of town... I have learned that I am not one of them. But, working out of town is necessary and unavoidable so I’ve made a certain peace with that. When I go out of town I try engage with whatever city I’m in as if I’m not a visitor by getting away from tourist centers whenever possible. One of my favorite out of town hobbies is to eat at a local diner. Local diners in cities are the best because there are so many stories and usually people interested in telling them. That’s how I deal with it, but yeah, it’s tough. You have to really want to do this, to do it. 

Was there ever a moment where you felt like giving up? What did you do to get through that time? 

Jessie: Someone recently asked me this and they laughed and gasped at my reply- but I think about giving up a lot! Hahaha. I think about what else I could do and what would be “steady” and “reasonable”. There’s an interesting thing when you finally achieve something you’ve wanted for so long. There’s a moment of relief and happiness and then almost an immediate worry feeling of “what now”??? After I debuted in Beautiful, I experienced the high and then started worrying about learning the rest of my tracks as a swing (having to be ready with 4 different roles). Then I moved over to Waitress and I think it’s there, the every day of it, the in rehearsals for most of my weeks, the prepping as an understudy and not always getting to go on because of this and that where I’m like - Woah, this is not what I dreamed it would be. ALL OF THAT SAID- I wouldn’t take back any of it. These experiences are truly life-impacting and lesson filled and oh so good when it’s good and when it’s shitty it honestly will never be as shitty as when I was cleaning up spit buckets from wine tastings (one of my side jobs). No, but, in all seriousness, I think about giving up at times AND the desire for anything else hasn’t been as strong as my desire to perform, connect, change the world, and impact people with art. Not yet. Maybe it’ll change and I’ll teach someday. Who knows! But right now, I’m just trusting my feelings and going with where my desire is most, which is performing. 

Gil: Honestly, no. I’ve been frustrated and extremely hurt by things in the business like anyone else but I can honestly say the idea of giving up has never been a serious notion in my mind. If anything, I would say instead that the failures I’ve suffered have invigorated new ambitions within me such that my goals have significantly evolved from what they were when I graduated college to now. I don’t say this to characterize myself as some unflappably strong person, quite the opposite, my reticence to “give up” is, I think, a direct result of a very real character flaw that I have been burdened by my whole life. I’m stubborn. 

What is the biggest surprise you’ve discovered about this industry? Biggest disappointment?

Jessie: Biggest surprise- the work has just begun. Also, the Broadway schedule is NOT to be laughed at! It is NO joke! Goodbye baby showers, weddings, life things... You miss a LOT on this schedule. Biggest disappointment (but also a relief/releases the pressure a bit)- you will never ever stop learning and there is no such thing as perfect (only a disappointment to my perfectionist mind but I’m working on it!!). 

Gil: The biggest surprise: The check. The money you make on Broadway, at least the production minimum you make from the ensemble of a Broadway musical, won’t make you a Rockefeller. It is, for sure, a wonderful blessing to be employed on a Broadway stage and the check is better than anything I would make doing the same work regionally. But the truth (which I think is worth voicing because I certainly harbored different expectations within my imagination before I got to Broadway and I KNOW I’m not alone) is, as wonderful as the check is, it is ultimately ephemeral (shows close), and all the cliches about New York rent are very real. I think, for whatever reason, I got to the city and thought that if I could just make it to Broadway my financial problems would disappear, so it was quite a humbling experience the first time I showed up to a Broadway half-hour and sat at my station knowing I had an overdraft bank account. It was like, “Surprise, you’ve made it! You’re on Broadway! Now let’s hope you make this month’s rent...” I’ve gotten a better handle on things and figured out ways of staying on top of my account balances, but the struggle is still real.

The biggest disappointment: I HAVEN’T MET STEPHEN SONDHEIM!!! Like not even backstage after a show. The real dream, of course, is to get cast in a revival of one of his shows and he’s actively involved but I’ve been here almost ten years and I’ve never even been in the same theatre auditorium as the man, much less an audition room. It’s extremely disappointing!!! 

Jessie: Okay, jumping back in here to agree with Gil and say YES I HAD A TOTALLY DIFFERENT IDEA as to what Broadway money was. I’m grateful I’m currently able to pay my bills and my rent but on the standard ensemble production contract it’s just not what I thought it was...especially considering the 8 show a week schedule and what that really means with rehearsals and all the work put in. Again, I am VERY grateful I can pay my rent doing a Broadway show, I just had a totally different idea of what that money would look like. I think most people do. I know half of my friends and family definitely think I’m “rich” now and I ain’t rich! We also live in an expensive city, that’s just what it is. But maybe I’ll be “rich” one day— when tv/movie work comes! When I can pay my rent/mortgage and buy my parents a house and I’ll know I’ve made it! 

It’s very clear even by lightly stalking social media how incredibly supportive you both are for each others careers. It’s beautiful! Did you ever go through a time of playing the comparison game with each other? Or did it come naturally to be content and supportive of both of your journeys? 

Jessie: Yes! (I think I answered this in the long-distance question so you can move some of those answers down here if you want.) Gil is very supportive. He truly believes in me more than I believe in myself. I say that with everything in me. If we’re being for real for real—sometimes I wish Gil could baby me a little when I’m feeling the disappointments of the biz. He has such a good mindset about it all and is really good at caring about the work but not caring about the bullshit (the “who is doing what and why” and “why didn’t I get picked”). He’s good at letting his auditions go. I’m a results-oriented person. If I don’t get a callback or hear exactly WHY it didn’t work out I mourn it a bit (I’m working on it- bc it’s not exactly healthy to be that way) and Gil automatically greets those feelings with tough love when sometimes I’m like “CAN WE BE SAD PLEASE?!?!”. SO- we’re always working on how to be there for each other. That’s a constant ebb and flow- understanding how YOU feel but coming to your person and being there how they need you to be. That’s a relationship. So I think the basic foundation of support is 100% there but it’s something we’re always working on because we’re different human beings and what we need changes. When it comes to him?- I think Gil is one of the smartest, big-hearted, hard-working, openly creative, and BEAUTIFUL souls you could be around and work with- and I’m pretty sure everyone he’s worked with will say the same.. so yeah, I support that 100%. 

Gil: I find it really easy to be supportive of Jessie because I really think she’s amazing. She’s right that I’m not one to lament the results of auditions or the myriad other disappointments that pop up during the day to day life as an actor in this business so I don’t even think about her and I in terms of business long enough to stew over the differences. I will say that Jessie gets WAY MORE auditions than I ever get! HAHAHA! if there was something I would lament it would be that, but even that, I understand, is a by-product of her versatility and marketability. She’s beautiful, she’s talented, she’s friendly, she’s just great! How could I not stand behind a woman like that? 

What was the most important thing you did to get where you are? 

Jessie: I just kept going. Kept showing up...and I try to keep doing that. 

Gil: Ditto. I worked, I studied, and I kept showing up. I can’t say I’ve been my most impressive self in every audition I’ve ever gone to, I’m no stranger to the 99 “no”s that come before a “yes”, but I have had enough moments of brilliance in a room to get cast in two OBCs and a bonafide hit. I consider those accomplishments matters of persistence over anything else. 

Where are you on your mountain? 

Jessie: Wow. Hmmm. Some days and moments I feel halfway, somedays and moments I feel at the bottom, just beginning...this question makes me excited though because does anyone ever get to the “top”!? 

Gil: I’m standing on the top of one mountain looking at the much taller mountain ahead that I want to climb. 

RAPID FIRE: 

Favorite Broadway show:

Jessie: Currently?! There’s so much I HAVEN’T seen. Currently, I am a BIG fan of my husband’s show, Beetlejuice. I think it’s SO good- SO smart- SO hilarious! I listen to it around the house (and not just bc we get royalties but bc it’s so good hahaha). 

Gil: Before it closed, Beautiful, was my favorite show on Broadway and that was even before it was Jessie’s debut. I was so thrilled by that show every time I saw it. I thought the production was gorgeous, slick, and engaging. I don’t particularly like jukebox musicals (I’m one of those people) but I was always pleasantly surprised at how satiating and entertaining an experience that show was. 

Gilbert, favorite role you’ve seen Jessie perform?:

Gil: I’m partial to her turn as Squeak in, The Color Purple, mostly because I got to see it right up close as Harpo, but my favorite memory of Jessie onstage was watching her play, Dorothy, in a production of, The Wiz. She was up there LIVING in all those big numbers and I was in the audience just mouth open the whole time! I think my favorite thing is hearing her let loose on a big belt song. 

Jessie, favorite role you’ve seen Gilbert perform?:

Jessie: There’s something about the first time I saw him on Broadway- he was on for Mutumbo in Book of Mormon. I’ve never been so proud watching him f**K a frog center stage hahaha. 

TV show you binge:

Jessie: Together? We’re into The Good Place otherwise he’s always (always) watching The Office and I’m always catching up on This is Us and How To Get Away With Murder 

Gil: THE. OFFICE. 

Podcasts you like:

Jessie: The Daily is my go-to! 

Gil: I never got into podcasts. I prefer to read. 

Religious, Spiritual, or nah?:

Jessie: Spiritual. There’s definitely a higher power! Praise GOD! 

Gil: Very spiritual, not very religious, although black gospel music fills my soul as much now as it did when I was a church kid growing up. 

Former side hustles:

Jessie: temping (worked some wine shows where people spit the wine out in buckets WHO DOES THAT), catering, babysitting... 

Gil: I worked as a salesman at GuitarCenter when I first moved to the city and I loved it! I worked at Ample Hills Creamery serving ice cream over a summer and I loved it! And I once hung lights in the ballroom at The Waldorf Astoria for an aerial circus show and I loved it! I love to work the side hustles. Of course, you don’t want them to last forever but I find the clientele interesting at those jobs. 

Any bad audition stories:

Jessie: I’ve cracked in a callback during one of musical theater’s most EPIC songs and it was in front of a LOT of people (all of the creative team, ALL of the producers- AND they were taping) and I won’t say the show in case that role works out one day (THEN I will tell the story..hahaha). 

Gil: Once, during the process of auditioning for, A Bronx Tale, I showed up over an hour late to an invited dance call for Sergio Trujillo. The reason I was late was a mixture of train trouble and subsequent traffic that occurred when I got into a taxi and the driver decided to take a tunnel instead of a bridge, but neither of those are things choreographers with Sergio’s resume tend to accept as legitimate and I am sure, had I not already done well with the music supervisor, Ron Melrose, and the director, Jerry Zaks, in the days preceding, Sergio would have denied me the audition outright. I managed to still book the show but throughout the work session Sergio made no effort to mask his annoyance at my tardiness and it made for quite an awkward first impression. I’d like to think that throughout the rehearsal process I proved to be worth the wait but I’ll never know. 

Favorite audition song:

Jessie: I sing a lot of pop/rock and I love when I get to sing Whitney Houston. “How Will I Know” is one of my faves. 

Gil: I love to sing, “Something’s Coming” from West Side Story. I have never booked a single job with that song, but I love any audition where I get to sing it. 

Best part of being married to an actor:

Jessie: the understanding of the schedule.

Gil: She added books I’d never read and plays I’d never heard of to my bookshelf. 

Job you didn’t expect to book:

Jessie: I didn’t think I would get Sarah in Ragtime at Milwaukee Rep. I SO thought they would go with a name. I’m so happy I got to revisit that show and with such a great company. 

Gil: A Bronx Tale. I’m telling you, the look on Sergio’s face when Merri (Merri Sugarman who happens to be my favorite casting director in the city) brought me into that studio... I was sure that was gonna be a solid, “hell no.” And I totally understood. 

Biggest beef with the business:

Jessie: The lack of diversity. TRUE diversity- not just putting in a single chocolate drop or two in the ensemble/understudy situation... and that it’s all legit a BUSINESS. A lot of people don’t really care about you, y’all.. not even the art of it. 

Gil: This is a whole other article, but my biggest beef with the business is the lack of investment in work that shows the complexity and fullness of the current black American experience. 

Anything you’d like to promote?:

Jessie: Gilbert Lewis Bailey II and how I love working with him and we want that opportunity again. Winnifred and Dauntless? Audrey and Seymour? Shoot we don’t even have to play a couple in the piece just hire us :) we’re a good time! Hahaha

Gil: I am so here for a Baileys-do-Little-Shop-Of-Horrors-Moment!!!