Power Couple: Jessie Hooker-Bailey and Gilbert L. Bailey II

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” (que studio audience: “awwwww”) interview! Can you introduce yourselves to our readers? 

J- YAY I’m soooo excited to get to do anything couple-y :) I’m Jessie Hooker-Bailey! I’m currently in Waitress the musical on Broadway until we close up shop Jan 5! 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 let’s us get you ;) ) 

G - 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? 

J- 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 and 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. 

G - 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 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? 

J-Yeahhhh. We met doing a show which was super special (I was Squeak and he was Harpo in the Color Purple at Milwaukee Rep) but then 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 it’s 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. 

G - 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? 

J-Someone recently asked me this and they laughed and gasped at my reply- but I think about giving up a lot! Hahah. 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 everyday 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 some day. Who knows! But right now, I’m just trusting my feelings and going with where my desire is most, which is performing. 

G - 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?

J- 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!!). 

G- 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, absolutely, 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 lets 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!!! 

J- 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? 

J-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%. 

G- 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 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? 

J- I just kept going. Kept showing up...and I try to keep doing that. 

G- 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? 

J- Wow. Hmmm. Somedays and moments I feel half way, somedays and moments I feel at the bottom, just beginning...this question makes me excited though because does anyone every get to the “top”!? 

G- 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:

J-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). 

G- 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?:

G- 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?:

J-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:

J- 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 

G- THE. OFFICE. 

Podcasts you like:

J- The Daily is my go to! 

G- I never got into podcasts. I prefer to read. 

Religious, Spiritual, or nah?:

J-Spiritual. There’s definitely a higher power! Praise GOD! 

G- 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:

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

G- 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:

J- I’ve cracked in a callback during a 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..hahah). 

G- 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:

J-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.. 

G- 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:

J- the understanding of the schedule

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

Job you didn’t expect to book:

J- 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. 

G- 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:

J- 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. 

G- 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?:

J- 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! Hahah

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