Winkler Also Has Role Formerly Played By The Material Girl In Sights

In the early 2000’s, Hennessy Winkler was called back for a Broadway Oklahoma! tour for the role of Ado Annie. Fast forward decades later, and this multi-faceted trans performer is playing the role of Wil Parker, Annie’s boyfriend in the nationwide touring production of Oklahoma! I sat down to talk to Winkler (as the traveling tour of Oklahoma! rolled into Philadelphia at the Fofrest Theatre) about bringing trans representation to this Rogers & Hammerstein classic, his work with comedian/actress Judy Gold on the Kill Me Now podcast (and what he learned from her) and what his dream role just might be….

Michael Cook: Congratulations on your first national tour with Oklahoma!; how does it feel? 


Henn: It is incredible. I am so grateful, I love it. I love being on the road, I love this iteration, I love the character, and I am just very grateful. 

MC: You have come a long way from being on the hilarious and thought-provoking podcast Kill Me Now with actress and comedian Judy Gold. 

H: That is awesome you know me from there, that is so much fun!


MC: What do you think you are enjoying the most being a part of Oklahoma

H: I am enjoying being on stage for eight shows a week, being able to do what I love and make some money at it! 

MC: When did you realize that live theater was going to be your passion? Is there one show that just lit everything up and made you realize that this is what you wanted to do? 

H: Yep; it was Jerome Robbins’ Broadway, around 1988-1989. After they did it on Broadway, it was toured and I saw it in California. I didn’t know whether I loved it or hated it as I was watching it, it was weird. There were all these grownups on stage acting like goofballs and I was the only kid in the audience; grownups were watching all of these other grownups do kids stuff. I hated it, then Act 1 ended and I was devastated; I wasn’t ready for it to be over. I was so relieved to hear that there was a second act, and I realized it was too much for me to ignore, I didn’t know if I loved it or hated it at that time, but I knew that I would be doing it for the rest of my life. 


MC: Oklahoma! is such a classic show; what do you think about the show makes it applicable to what is going on today and such a must-see production? 

H: Everything that is going on in the world today has been going on, I feel like it is just what we as humans become conscious of what is going on, and I feel like our consciousness has really shifted. The original musical came out before the movie and it had some really dark themes in it. The movie also has some, it has someone trying to convince someone to commit suicide, things between men and women, etc. When the film came out there was a war starting, and when the play came out there also a war starting; people want to come to the theater to be lifted up, not be reminded of the darker side of humanity. Rogers and Hammerstein wrote this and kept some of the darker themes, but the costumes, dancers, and chorus girls softened it and people didnt have to think about life too much. People could think about the music, the dancing and leave tapping their toes feeling a little lighter than before.

I feel like we’re in a different kind of vibe now, where people want a little more honesty, truth, there is a little more sarcasm and darkness in our entertainment. We want to be entertained as well and I think this musical does that. We have all the original tunes, and the orchestration is a little more different, it is a little bit more blue grassy, which I love. For the most part, it is the same script and score, we have not really changed that much. We are incorpating things that were left out of the movie and turning it on its axis a bit, and looking at the themes that have always been there that have been danced and sung over. 


MC: You make a good point, Oklahoma! itself was of its own time and it is truly being shown for today’s audiences in this iteration, while also staying true to its classic roots. 

H: Absolutely.  The casting is much more diverse than golden age musicals are normally cast, so I think that brings it into today also, so we can stop this whitewashing of everything in America. 

MC: Featuring a trans performer in Oklahoma! is not so much a brave step but a necessary step. I think it is crucial that we showcase all kinds of people in stage productions of classic material. How does it feel for you? 


HW: It feels incredible. I love seeing my trans brothers get work and really start to do things. You have Iris Menas that was in West Side Story, Mareya Salazar just got a CW show, we are really starting to come out and do more. I think our trans sisters have been a bit more visible, a lot of people don’t even know that trans men are a thing and we definitely fly under the radar; trans male erasure is a real thing. On one side, there is a little bit of privilege that comes with that, on the other side there is a bit of a loss of identity where we are hanging out in the wind tunnel saying “we’re here too”!

MC: As a trans person. what does it feel like from your perspective to see laws passed like the “Don’t Say Gay” law that just passed in Florida? 

HW: It feels like it always felt; this is what every underprivileged group goes through. Two steps forward, one step back. It is not surprising, it is growing pains. It is part of the countries’ transition. It is not just the country that is transitioning, it is everyone around them too. It feels like we have forgotten our trans history as human beings and our ancient trans history. We really have done a number on our psyche with things like religion, politics, and how people use religon to control others. Now I don’t think spirituality/religion is innately bad, but it has been used as a weapon for a long time. I know for myself it kept me down for a long time, I thought I was going to be spending an eternity in hell. It doesn’t surprise me that people are making laws who aren’t queer or think that they are going to be spending time in hell for an eternity would flop like a fish out of water; it is just this weird panic…


MC: You are absolutely right, it is two steps forward and one back. Trans performers like you are in Oklahoma!, trans performers like MJ Rodriguez are getting Emmy’s for her work in Pose, and then laws like the “Don’t Say Gay” law is passing in Florida, where there is massive LGBTQ representation. 

HW: Once there is a chink in the damn, the water is going to come in; that is what truth is and you cannot rebuild the damn. I am from Hawaii and they were one of the first states to legalize gay marriage. They legalized gay marriage and then a couple days later, they took it back.

MC: if you could manifest any show that you would like to perform in, what show would it be? 


HW: It would be this one; this would have been it if you had asked me before I got it. I would also love to develop a new musical that goes to Broadway. You know what would be cool?-A League Of Their Own-The Musical! I would like to see that happen. 

MC: A trans man playing Madonna’s role of Mae would be a delicious touch of ironic casting, wouldn’t it? 

HW: Yes! I would definitely play Mae!


MC: What is the one lesson that Judy Gold taught you that you have taken forward in your career that has stayed with you? 

HW: Showing up; she taught me about showing up. And perseverance, really. Keep showing up; her career has spanned decades and she has done so much, and she keeps showing up and putting herself out there. And she is still doing some amazing things. 

The Tony Award-winning revival of Rodgers & Hammerstein’s Oklahoma! is playing at the Forrest Theatre (March 8 – 20), in partnership with the Kimmel Cultural Campus. Tickets are available here

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