Jesse James Keitel And Sydney Freeland Boldly Go

Producers of the newest streaming series in the Paramount+ Star Trek franchise have boldly gone where no television show has gone before: Casting an out transgender woman actress—the incredible Jesse James Keitel—in an episode directed by an accomplished out trans director, Sydney Freeland.

And the result is not merely a Pride Month bonus for LGBTQ+ fans, or just another rainbow moment in pop culture history. It’s also an exciting, entertaining and action-packed episode of Star Trek: Strange New Worlds, the series that depicts the adventures of the U.S.S. Enterprise a decade before Capt. James T. Kirk commanded the famous starship.

Episode 107, “The Serene Squall,” also features romance, comic relief, suspense and intrigue, as well as a plot twist involving pirates. So, be warned, me maties: From this point forward, there be spoilers ahead!

Meet the Villain

Keitel plays a nonbinary space pirate wreaking havoc in what Capt. Christopher Pike calls the “wild, wild west” frontier of the galaxy. Pike, played by Anson Mount, is captain of the Enterprise in this era, and Keitel’s character is Capt. Angel of the dreaded pirate ship, Serene Squall. When we first meet Angel, they’re masquerading as a former counselor turned relief worker named Dr. Aspen. They stranded the real Aspen on a faraway planet as part of their plot to free an infamous, incarcerated renegade Vulcan, whom they love.

Angel lures the Enterprise into a trap in order to use Lt. Spock, played by Ethan Peck, as bait to free their lover. And that lover is ultimately revealed to be none other than Spock’s half-brother, Sybok, a character from Star Trek V: The Final Frontier, regarded as most fans’ least favorite film in the franchise, the one directed by the original Capt. Kirk, actor William Shatner. Although Spock, Pike and crew finally outwit Angel, the crafty villain escapes.

Both Keitel and Freeland joined me for separate one-on-one interviews.

Jesse James Keitel

Keitel said she believed our chat was her first-ever with an out trans journalist, as far as she knows. The following has been edited for clarity and contains spoilers.

Jesse James Keitel: You know, actually, I don’t know if I’ve ever been interviewed by a trans person, that I know of? I may have.

Dawn Ennis: It could have been somebody who hadn’t come out. And you play a nonbinary character or is that part of the whole charade by Capt. Angel pretending to be Dr. Aspen?

Keitel: That’s a great question. Actually, the first time that question was posed to me was this morning. I saw it on Twitter. I was like, “Oh, I actually don’t know the answer to that.” My assumption was both of them are nonbinary. Nonbinary has played a very complicated role in my own identity. It gave me a lot of freedom; It was limitless. There were no rules within that for me. But then I eventually felt more restricted by that. So, for me, living in a more binary label eventually ended up feeling more like home, especially when we were filming. I am very much nonbinary now. The part of me that is nonbinary is just that, none of this is real, none of this matters. We’re all just sacks of flesh rotting on a giant rock in space, so we might as well just make the most of it we can.

Ennis: I was telling someone, a trans icon I was interviewing, ‘You’re so calm about the state we’re in right now. I want to scream about how dangerous and terrible the situation is.’ And she told me, “You know what,. times change. Things will come, things will go. We just need to wait it out.” And I was wondering, just on a personal note, how are you handling Pride and all the hate that’s out there right now?

Keitel: Pride is so interesting to me this year because I’m also celebrating the release of Queer As Folk, and I’m infinitely proud of the stories I’ve gotten to tell on that show, specifically with my character, who’s a trans woman who’s beautifully flawed and complicated. Maybe I’m falling into a little bit of a villain phase!

Keitel (cont’d): It’s hard to feel good about all of our accomplishments when there’s so many things and so many people trying to legislate us out of existence, trying to make sure there can’t be more trans people to come after us, people who wish I wasn’t on Star Trek or who wish I wasn’t part of the Queer As Folk universe. It’s sad that the small bits of hate do stand out more than the love sometimes. But Pride for me this year? I felt like, in years past, Pride for me was, “Where do I fit in, into this community? Where do I fit in?” I know where I fit in now. Now, Pride is where do we, as a community, fit into the culture. And, being a lead on Queer As Folk, having this moment on Star Trek, that’s where I fit into the culture.

Ennis: You made history. You are the first out trans woman guest star in Star Trek history. And it’s something that every single person I’ve spoken to at Star Trek has heard me complain about, too. “Please tell [executive producer] Alex Kurtzman we need a Star Trek character who is a trans female.” And you know, it’s great to have [trans nonbinary actors] Blu del Barrio and Ian Alexander. I don’t want to dismiss their accomplishments. I love [out gay actors] Wilson Cruz and Anthony Rapp. But I wanted someone like us, you know? I wanted to see someone like us.

Keitel: I agree. I feel the same, the same way, because I know there’s probably complicated thoughts on me playing a villain in this, too, which I guess, you know, queer people have had a really complicated history in TV and film, you know?

Ennis: Thank you, Law & Order.

Keitel: Thank you, ‘Dead Body Number Seven.’ However, I’m like, also: Fuck that. Let me be a villain. It’s not my character’s queerness or her transness that makes them a villain. It’s love. The real villain of the story is love.

Ennis: Isn’t it more fun being the villain? I was a child actor and I have a trans daughter who wants to be an actor. Come on!

Keitel: I mean, we’re all the villain Find me one bitch that ain’t the villain, you know? And I think robbing trans people of the experiences that we give cis characters is a disservice to the community. That is not activism. Maybe there will be people who disagree with me. I am thrilled that by your words, that the first trans woman guest star is a villain, because you know what? You won’t forget it. Not only that, but she gets away. Little spoiler. She gets away!

Ennis: Will you come back, if invited?

Keitel: I would sell my kidneys, both of them, to go back.

Ennis: Tell me about Queer As Folk and how that opportunity came about. You’re a lead! That’s huge.

Keitel: She’s a lead baby. That came up very unexpectedly. I was about to sign on to more Big Sky and this role that felt like home just showed up on my doorstep. And I had a tough decision to make. And I made it very quickly.

Ennis: There are going to be trans girls who are going to see you and they’re going to think, ‘I can do that. That could be me.’

Keitel: ‘I can take over that starship!’

Ennis: Yeah! It’s opening a world to trans girls who, you know, never saw themselves on TV before. And I’m just wondering what that means for you? I’m someone who grew up wanting to be who I am. I knew since I was four; It took me until 45 years later to realize this authentic life. What does that mean for you to be sending a message to young trans girls?

Keitel: Well, I hope I’m not just sending a message to the young ones. I hope I’m sending a message to the ones of all ages who may need to see someone like me on TV. I’m slowly building the career I needed, to see someone who is, you know, like me. I prevented myself from transition for years because I thought I would never be successful if I leaned into my queerness. I thought I would only make it as an actor if I hated myself and walked through the world with a very narrow experience, very limited experience of what my life could be. Not only did my career expand, but I expanded. My life became fruitful after I leaned into myself. And I hope people who see me on TV in a batshit crazy role like Angel on Star Trek: Strange New Worlds can lean into themselves. It can give them permission to live, to lean into themselves, to avoid the way I tortured myself for years.

Ennis: My BFF Melody Maia Monet, who also happens to be a trans woman, told me, “Her little black outfit is sexy AF.” I can’t imagine it was comfortable, but that catsuit was something else.

Keitel: I felt so hot in that catsuit. However, I am pale as a ghost and I always wear sunscreen. The one day I didn’t wear sunscreen, I went for just a short walk around Toronto. It was the day before filming! I had one of the worst sunburns of my life for that first day of filming. The first scene we had to film was me in Spock’s quarters, where I go sit on the couch. Every single second in that suit was like a screen door scraping against my soul. It hurt so bad!

Ennis: Since you mentioned Ethan Peck. What’s he like? I think a lot of us have this fantasy of being Nurse Chapel in that episode.

Keitel: He is the kindest costar I could ever ask for. It was so much fun shooting with him. Truly, I felt so, so lovingly welcomed by him and Rebecca [Romijn] and just truly everyone, the whole cast. The crew of that show, it’s like, I wasn’t a guest star, I was part of the family. It was really special. And it reinvigorated a love for acting that I really desperately needed at that time.

Ennis: Tell me about working with director Sydney Freeland.

Keitel: Sydney was the first trans woman I’ve ever worked with in that capacity. And there wasn’t a learning curve. I didn’t feel like the token trans person in the room. I felt like we were telling stories that were complicated and nuanced. Having a trans person behind the camera, I could trust that we were in good hands. Yes, I am playing a villain. And yeah, there are going to be people who have opinions on that, because, you know, queer-coded villains, etc., etc. This is explicitly a queer villain. There’s a difference. There’s a huge difference. And I trusted her so much, and she’s become such a dear friend. And yeah, I cried after we filmed my last scene. Calling this experience a gift is quite the understatement.

Ennis: Knowing you were going to talk to me and having spoken to all these reporters all day long, was there anything you wanted me to ask that I didn’t ask? Anything you want to make sure I put in my story about you or about Queer As Folk or about Star Trek. I just want to make sure you have that opportunity.

Keitel: That’s a great question, Dawn. No one has ever asked me that. It probably sounds cliché, but this role was a lifelong dream. I don’t know if I believe in manifestation, but I feel like I manifested the shit out of this one. I’m such a Star Trek fan. I’m such a sci fi fan. And getting to walk onto the Enterprise and captain the Enterprise…

Ennis: You sat in the captain’s chair!

Keitel: Not only did I sit in the chair, I lounged in the chair, and then I shot Spock from it. I appreciate what you said before, about young trans girls who may watch this and see themselves do something really fucking badass and be inspired by that, and I hope that is the case, because I wish I grew up with villains like Angel. I think it’s so cool to be unapologetically villainous and in love and sexy and truly go for it. Having the freedom to take a risk like that. It can make me emotional saying that, not only did I have my own selfish reasons get to be part of this world, but there’s also impact on people. These stories and these characters have a legacy. And, you know, just like how Blu and Ian kind of paved the way for trans people in the Star Trek universe, I hope Angel can open the door somewhere.

Sydney Freeland

This was my second-ever interview with the award-winning director.

Freeland revealed her identity to me in a 2015 interview to promote Her Story: a look “inside the dating lives of trans and queer women as they navigate the intersections of desire and identity.”

“I’m transgender myself,” Freeland told me at the time. That’s an aspect of her that actor/writer/producer Jen Richards, cocreator and costar Laura Zak, costar Angelica Ross, and producer Katherine Fisher said they didn’t know when they approached Freeland to direct.

“I got the script and I read it, and I think the thing I really responded to was, it was showing me something I hadn’t really seen before: a trans woman and a lesbian woman having a relationship.” But it was more than that which drew her to the project, Freeland told The Advocate in 2015: “On a deeper level, one thing that attracted me was that in media, trans women have a tendency to be sexualized, fetishized, and in Her Story it was kind of the opposite. It was two people getting to know each other. Hopefully that’s what will attract audiences as well.”

Sydney Freeland: Yes! Yes! I remember you and I remember your name, and yes, I remember that.

Ennis: I wasn’t sure where you were in your journey in 2015. But I think what it did was, it lent Her Story that much more authenticity, that the person behind the camera and the other people in production were identified as trans and nonbinary. It makes a difference, don’t you think?

Freeland: It absolutely does. Back then, it was like “Wow, we have folks on the crew that are trans!” And actually two of the folks working on that project have since come out, one as nonbinary and one as trans. I remember feeling it was a very new and exciting experience at the time. We still have a long way to go, but I think we’ve been able to kind of expand the roles that people can play and where they are, behind the camera, in a really great way.

Ennis: What I always say is that being trans is the fifth most interesting thing about me.

Freeland: Yeah, that’s true. I love that.

Ennis: Tell me about the people you’re working with, because some of the directors who have sat in the chair that you’ve sat in are just some of the most amazingly talented people, not just the directors, but also the producers and the talent. And I am blown away as a lifelong Star Trek fan at how amazing Strange New Worlds has been in just seven episodes. Full disclosure: I’ve seen eight, but fans will only have seen seven.

Freeland: Oh, amazing. Well, I’m glad you like the show. It’s very humbling, but it’s also very inspiring because you’re stepping in some really, really big shoes. And, you know, it’s a dance between you want to get it right, you don’t want to mess it up, but you also want to tell a good story and do the job that they’re there to do. And so it’s always a balance. And I think I think the one thing we had working in our favor is an excellent script, an excellent cast and then an excellent crew. So, I can come in, but I can only do so much as director. You need good people around you, really good. You need good actors working for the camera. And, you know, I was extremely fortunate that I had all of those things. And then you add in Jesse James Keitel, who was, for me, a revelation, and absolutely adored every second of working with her. You know, you bring her in and I was very, very pleased with the result.

Ennis: She’s a phenomenal actor. What was it like for you working with her? Was it different in any way? I mean, this is for the cisgender people reading this: Is it any different directing a trans actor, being a trans director? Is there a difference that, you know, someone who is cisgender can or can’t understand? Because, like I said, being trans is just one part of our experience. It’s not everything. And I’m just wondering if you find that there is some kind of difference in either casting or working as a director who’s trans.

Freeland: Yes and no. No, it is not different, insofar as the process is the process. The character is still the character, you’re still the director, the actor is still the actor. And you want to work together to create this performance. And if it’s well written, there should be this aspect of humanity to the character that is the same with whatever the actor is whether they’re trans, nonbinary, whatever their background is. If there is an element of humanity to this character, then then the process is the process.

But then I think here’s where you differentiate things. There’s little things about working with a trans actress; There can be a shorthand, if that makes sense. The shorthand of the trans experience. But then you also bring Jesse’s life experience to the table, my life experience to the table, and we have different experiences ourselves. But then that lived experience is what ultimately elevates that character and gives it that nuance. And so I think with her, I think there was that lived experience that was absolutely crucial to to fleshing this character out. And we want to have a portrayal that felt lived-in and kind of matter-of-fact and not apologetic. It’s almost as if you’re you were lucky to be graced by the presence of Dr. Aspen, or Angel.

But it’s also interesting too, because I’m also a Native American and there are certain parallels, right? Like you have the lived experience as an indigenous person, a Native American person, and that does bring something to the table. What I found is that the more different we are, it’s ultimately it’s our similarities that bring us together. Those are the things that I try to focus on and portray, because those are things that are relatable to everybody.

Ennis: Star Trek has a somewhat, let’s just say, troubled past when it comes to Native American portrayals, from TOS to TNG, as well as Cmdr. Chakotay in Star Trek: Voyager and Star Trek: Prodigy, in casting, you know, non-indigenous actors as Native Americans. Do you hope to return to Star Trek and perhaps rely on some of your own Native American ancestry to inform your work?

Freeland: Oh, if the opportunity presents itself, yeah, I’d love to do that.

Ennis: What’s the reason why no one uses the word “nonbinary” to describe either Aspen or Angel in the episode, just they/them pronouns? I imagine that was deliberate.

Freeland: I have to defer to the writers, but because we’re in the 23rd century, the year 2250-something or other, you know, roughly, what we’ve said is that even the idea of “nonbinary,” we may have evolved past that label.

Ennis: What else are you working on that we will see, that you must be excited about?

Freeland: I’m currently directing on a project for Marvel and it’s called Echo. It’s a spinoff from [the Disney+ streaming series] Hawkeye.

Follow Sydney Freeland on Twitter by clicking here. Click here to follow Jesse James Keitel on Twitter and she’s also on Instagram. Also: You’ll find a full recap of this episode by Jay Stobie at startrek.com or just click here. And if you’re curious about the actress’s last name and her distant relationship to actor Harvey Keitel, find out more here.