You know those shows you’ll see that just strike such a chord with you, and you aren’t sure why until later in life? If not, let me tell you…it is a whirlwind. I remember a few years back, I decided to go see this show called It Shoulda Been You at the Brooks Atkinson Theater. I remember a lot of things about that production that moved and shocked me, I just didn’t realize how much the show would impact me until well after the show’s final bow. This week, The Theatrical Board is writing about the relationship between theatre and sexuality. However, there are more issues in this show aside from sexuality that I’d like to discuss, so consider this part one of a two-part editorial. Just a heads up, there will be huge spoilers for It Shoulda Been You in this piece, so consider this your SPOILER ALERT before reading any further.
It Shoulda Been You takes place on the day Rebecca Steinberg is set to marry her fiancé, Brian, but the story is centered around her older sister Jenny’s experiences throughout the day. I could honestly go on and on about Jenny Steinberg, that character means a lot to me. But we’ll discuss that in part two. Instead, I shift your attention to Jenny’s sister, Rebecca Steinberg. Towards the end of It Shoulda Been You, it is revealed that both Rebecca and her fiancé are gay and in love with other people. Rebecca comes out to her family in a beautifully honest song called “A Little Bit Less Than.” I connected with a lot of songs in this show, but this one seemed to carry a weight of uncertainty. I felt connected to the song, but didn’t understand why. I wasn’t gay, so why did I find myself relating to a coming out song? I wouldn’t be able to answer that question until over a year later. That song became all too comforting during a time in my life when I was desperately trying to understand myself. There were days when I’d listen to it on repeat all day long hoping it would help me muster up the courage to come to terms with my own sexuality. Long story of self-discovery short, I came out as bisexual in 2016, and I’d be remiss if I didn’t credit that song as being a source of courage for me to do it.
I was happy for all of the couples that were formed by the end of It Shoulda Been You, but I found myself being fixated on the relationship between Rebecca and Annie. Annie Shepard, originated by Montego Glover, is the woman Rebecca is actually in love with and ends up marrying. I recall how flabbergasted I was to learn all of the layers of secrets the characters in this show possessed, but Annie’s secret relationship with Rebecca is the one that lingers the most in my mind to this day. The character of Annie Shepard is the first openly queer woman of color I’d ever seen on stage. I didn’t know at the time just how significant that was. Looking back as a queer woman of color myself, it brings joy to my soul knowing that a group often forgotten had representation on stage.
I’ll admit that I frequently watched bootlegs of the show after I came out, just to watch Montego Glover and Sierra Boggess get to interact with one another. That may seem kind of bizarre, but it is difficult to find characters that are queer women of color in general, let alone on the stage, and since Annie was the first female character that was part of the LGBTQ community and black I could find and relate to. It was important to me that I analyze everything I could about the character, especially as I was discovering myself. I hope that Broadway continues to embrace queer women of color so that other young women like me can have the feeling of acceptance Annie Shepard now gives me.
(Photo credit of It Should've Been You)