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How Tales of the City Avoided a Trans Casting Controversy

The Netflix revival of a beloved queer series brings back Olympia Dukakis as Anna Madrigal—and, in a crucial flashback episode, introduces trans actor Jen Richards as a young Anna.
Jen Richards in Tales of the City.
Jen Richards in Tales of the City.By Alison Cohen Rosa/Netflix.

When veteran actor Olympia Dukakis appears in Netflix’s upcoming Tales of the City, it’ll be her fourth time playing Anna Madrigal—the beloved matriarch of 28 Barbary Lane. Dukakis originated the role in 1993, in the original PBS miniseries adaptation of Armistead Maupin’s beloved novels, which quickly became a cult classic for its revolutionary depictions of queer life in San Francisco. She reprised Anna again in the 1998 and 2001 follow-up series. Eighteen years later, Dukakis is one of the only actors to appear in all iterations of the saga—alongside Laura Linney and Barbara Garrick.

The new limited series kicks off with the tenants of Barbary Lane throwing their beloved landlady a 90th birthday party. In typically queer San Francisco style, there’s drag queens, interactive art, and, of course, copious amounts of weed. But this celebration for a subversive heroine comes with a big asterisk. Dukakis, 87 years old, is a cis actor playing a trans character—a common sight on screens big and small.

Though he won’t speak for his colleagues—including Maupin and Tales of the City showrunner Lauren Morelli, a former writer on Orange Is the New Black—executive producer Alan Poul, who has produced every iteration of Tales, never considered casting anyone besides Dukakis to play Anna. “Having Olympia was critical to making the show again,” he said in an interview. “Olympia is clearly grandfathered in and paid her dues.” Just as importantly, he continued, “Olympia has clearly earned the right to finish out the role”—citing Dukakis’s “very bold” decision to play a trans character in the 1990s, a time when there was little trans representation in media.

Still, Morelli seems to know that Dukakis’s return has the potential to ruffle feathers. “We know how starved the younger, queer community is for authentic representation,” she told Vanity Fair in March. The team behind the new limited series hired a predominately queer cast and crew to make its story ring as true as possible; trans talent behind the camera included writer Thomas Page McBee and directors Silas Howard and Sydney Freeland. The new Tales includes of-the-moment story lines, like one in which Margot, a lesbian cisgender woman, considers how her relationship has changed now that her partner, Jake (played by trans nonbinary actor Garcia), has transitioned.

Even so, the younger queer community’s pursuit of authentic representation often involves calling out Hollywood for outdated and outmoded views and practices. Last year Terry Crews was lambasted for equating transgender people with “transracial” people, while Ellen DeGeneres was criticized for supporting Kevin Hart after his old homophobic jokes resurfaced—and Netflix’s “trans trauma porn” film, Girl, spurred an entire news cycle of its own. There’s a strong chance that at least a few viewers won’t be so forgiving of Dukakis’s legacy casting.

Yet Poul, who has already addressed Dukakis’s portrayal in other interviews, isn’t going to budge. “If we had re-cast the role with a trans actress who could play a 90-year-old woman, there would have been an enormous uproar,” he said. “That would have been a huge act of disrespect and sacrilege on the part of the fans, whom we owe a lot.”

Still, Poul and his fellow executive producers took pains to make the series’s latest iteration contemporary and inclusive. They reached out to Nick Adams at GLAAD to hold cast sensitivity training. Adams, a transgender man, works with networks and film studios to educate them about creating safe workplaces for trans talent and writing trans characters with nuance.

With an informed crew and an opening episode centered on Anna’s 90th birthday, the limited series’s arc quickly came into view. Morelli and her writers saw an opportunity to finally dive into Anna’s mysterious past. The original 1993 series depicts Anna already living on Barbary Lane, while Maupin’s final book, 2014’s The Days of Anna Madrigal, follows her teen years as Andy Ramsey in Winnemucca, Nevada. The in-between period—Anna’s early years in San Francisco—were rarely acknowledged in the Tales books or TV adaptations until now.

The new series, though, features a stunning flashback episode set in the 1960s, depicting Anna’s arrival in San Francisco. In it, characters played by Daniela Vega (from the Oscar winner A Fantastic Woman) and a slew of other trans actors take Anna under their wing. The episode culminates in a fictional depiction of the very real, very important 1966 Compton’s Cafeteria riot, a milestone incident in the gay-rights movement that preceded Stonewall by nearly three years.

And in this episode, Anna isn’t played by a cis woman. “If we’re to cast a young Anna, we knew we had to find a trans actress,” Poul said. The team located her in Jen Richards, the Emmy-nominated star and co-creator of Her Story. “Jen, to me, was the one actress I found who could be credible as Young Anna, the person who would then very much become Olympia,” he added.

It didn’t hurt that Richards is a trans activist, as well as a performer. In 2016, she was at the center of another controversy surrounding cis actors playing trans women: in an eloquent Twitter thread, she expressed her frustration after Matt Bomer was cast as a trans woman in the film Anything. Richards later uploaded a YouTube testimonial detailing the real-life implications of cis men playing trans women, like Jared Leto in Dallas Buyers Club and Jeffrey Tambor in Transparent. “These kinds of depictions actually do lead to violence against trans women,” she said in the video.

https://twitter.com/SmartAssJen/status/769936316922376193

But when it came to Dukakis returning as Anna Madrigal, Richards had no objection. “I never really had an issue with cis women playing trans women,” she said in an interview. “For me, the concern is: how does this affect trans women in the real world? When you watch Olympia as Anna, you walk away with the sense that trans women are women.”

Of Tales’ many trans characters, none are depicted using the tropes that have become commonplace across TV and film: there are no spiritual mentors, or tragic souls, or campy comic relief here. Instead, these characters are nuanced, at times messy, and always very real. As the flashback episode reveals, Anna is far from perfect: she almost immediately betrays her trans sisters. “People will be like, ‘Oh, she’s a fucked-up, selfish white trans woman,’” Richards said. “I also love the fact that it’s not so simple.”

In playing a young Anna, Richards had to evoke a 1960s housewife, assuming the aura of Olympia Dukakis while adding her own flourishes. “That’s intimidating as fuck,” she said. “I definitely had a little crisis of confidence.”

She confided in Poul, who put her in contact with fellow Tales star Laura Linney. The two actors spent three hours in Richards’s hotel room honing her character. Richards’s voice is naturally higher than Dukakis’s, so Linney helped with lowering her register while remaining resonant. In a twist of irony, “You have a trans woman having to lower her voice to match the cis woman,” Richards said with a laugh. “By the end of those three hours with Laura, I just felt this part is mine too.” She sees the dual portrayal as a beautiful balance, “a kind of way to retire that portrayal of Anna and enter this new one.”

Richards and Dukakis never actually met over the course of filming Tales; whenever Richards stopped by the set when other episodes were being shot, she said, Dukakis didn’t happen to be there. Then again, “Maybe we weren’t meant to meet yet,” Richards said. “I’m not playing Olympia. I’m playing Anna.”

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