Very Special Gay Episode: 15 Years Ago ‘Drop Dead Diva’ Cast Candis Cayne as a Trans Lesbian

Welcome to Very Special Gay Episode, a series where we recap standalone lesbian episodes from classic TV shows that are not otherwise gay. In this installment, we discuss Drop Dead Gorgeous season two, episode eight: “Queen of Mean.”


“A model who dies in a car accident and comes back to life as a fat lawyer” sounds like a deeply offensive 30 Rock sketch, but it’s not. It’s the premise of Drop Dead Diva, a heartwarming girly legal procedural that ran from 2009 to 2014.

Growing up in more of a Lost/Prison Break/24 family, I didn’t watch Drop Dead Diva when it was on air, but my partner did! And recently, fueled by a burst of nostalgia, we started rewatching it together for the low, low price of $11.99 a season. The first thing that struck me was how quickly the main character Jane stopped trying to lose the weight. This wasn’t your typical “woe is me for being fat and therefore unlovable” early 2000’s drivel. It was deeper. Jane was hot, desirable, and desired. Men wanted her, she had canonically good sex, was a great friend, and one hell of a lawyer.

The cast was populated with its fair share of queer icons: Margaret Cho plays Jane’s trusty, sassy assistant Teri, and Rosie O’Donnell is featured as the recurring character Judge Madeline Summers. Unfortunately both of those characters were straight. Rosie O’Donnell’s character even had a whole episode dedicated to suing a dating service for not finding her a suitable man. But then we arrived at season two episode eight, and I got more than I had ever dared to imagine from a pre-Obergefell comedy… not only were there dykes, one of them was trans.

Despite Time boldly announcing 2014 as “The Transgender Tipping Point,” it took several more years for trans actors playing trans roles to become industry standard. (Even last year’s Squid Game season two cast a cis man as a trans woman.) And yet 15 years ago, Drop Dead Diva got it right. Trans actress Candis Cayne plays Allison Webb, a trans woman in a legal battle with her in-laws over her wife’s possessions after her wife dies suddenly in a car accident. Her in-laws who, by the way, couldn’t even be bothered to attend their own daughter’s funeral.

This plotline rings true to the countless stories of queer people who lost their loved ones to AIDS, only to have their absent in-laws take away all of their late partner’s possessions and even their homes. Ultimately, that was the main goal of gay marriage. Yes, having the government recognize your love is great, but it’s more important to have a legal right to your partners’ possessions, to visit them in the hospital, and to make decisions about their care over an absent, homophobic biological family. This narrative is complicated in Drop Dead Diva by the fact that Allison had been legally married to her wife even though gay marriage was not yet legal in California. Allison and her wife had gotten married pretransition, so technically their marriage was straight, and therefore legally binding… maybe.

Here’s where I was expecting the episode to get problematic. The narrative in my head played out like this: Allison’s lawyers Greyson and Kim argue that because Allison is biologically male (whatever that means) their marriage is still a law-abiding straight marriage, plain and simple, transphobia saves the day! And initially, that is what Greyson and Kim suggest. But Allison immediately shoots it down, “When I transitioned, Melanie stood by me every step of the way. By saying I’m a man denies everything that we went through. Please, find another way.” And find another way they do!

After a suggestion from Jane, Greyson uses the logic of Littleton v Prange, a real case that invalidated marriages between men and transgender women in the state of Texas based on the fact that same sex marriage was illegal in the state and Christine Littleton, a transgender woman, was assigned male at birth. He argues that according to this logic, Allison’s marriage was still legal, as she was also assigned male at birth, a distinct difference from being male. Shockingly enough, this TV argument has a real legal basis: After Littleton v Prange, lesbian couples were legally allowed to marry in Texas if one of them was a trans woman.

The episode ends with Allison winning her case; she is named as her wife’s next of kin and retains legal ownership of their possessions. Not only that, Greyson, who had originally been uncomfortable with the case, even misgendering Allison once (but only once! And not to her face! Shockingly sensitive for the time!), gives an impassioned speech about how Allison’s case was arguing for the existence of true love. “What these two went through… and they stayed together. It makes you believe that love can conquer all, and nobody should be able to take that away from them.” Even the transphobic father-in-law comes around, telling Allison, “I can never forgive myself for turning my back on my daughter. Now I’ll never see her again. Thank you for making her happy,” before giving her his mother’s necklace. It’s a heartwarming tale of trans acceptance and queer love conquering all, and something I was not at all expecting from an episode of a sitcom that came out in 2010.

My partner and I cried as we watched holding each other in our bed. As a trans lesbian couple, I don’t think either of us expects to see our relationship used as an example of true love in current media, let alone in a show from before gay marriage was legal. So often trans characters are relegated to corpses, punchlines, boogeymen, and cautionary tales. I can name so many examples in media of The Trans Struggle™, and yet so few of trans people falling in love, and even less so about that love being legitimate in the eyes of your average cis lawyer.

It’s no secret: Things are scary for trans people right now. The Democrats are shying away from defending us, Joe Biden signed a transphobic bill into law, Kamala Harris tried to use Trump’s record of providing gender affirming care to prisoners as a gotcha, and Trump has used his first few days in office to aggressively attack trans rights. This is reflected in our media. One of the most beloved children’s book series was written by a virulent transphobe who continues to benefit off the IP as it’s spun off into prequels, theme parks, musicals, and TV adaptations. Matt Walsh and The Daily Wire produced What is a Woman? and Ladyballers, and even the Olympics is full of transmisogynistic vitriol directed at cis women of color.

Our enemies are doing everything they can to delegitimize our existence. But maybe if we can continue to showcase our beautiful love stories, the kind I see at every bar and house party and friends wedding, the kind I see in my own home, there’s hope. Because, to paraphrase Drop Dead Diva, queer love makes you believe that love can conquer all, and nobody can take that away from us.


Drop Dead Diva is available to buy.

Before you go! Autostraddle runs on the reader support of our AF+ Members. If this article meant something to you today — if it informed you or made you smile or feel seen, will you consider joining AF and supporting the people who make this queer media site possible?

Join AF+!

Sunny Laprade

Based in NYC, Sunny Laprade is a standup comedian, storyteller, writer, and producer. Sunny performed her first hour of comedy at Alfred University in 2017 at just 17 years old. She is the current host and producer of T4T Comedy, a monthly all-transgender comedy show. Her first 75 minute comedy special, Queer Enough, which she filmed, wrote, and produced, ran for two nights to sold out audiences and was released to the public on YouTube in 2022. She is a staff writer for Late Stage Live, and her variety hour Dolls on Tour is currently touring the country!

Sunny has written 1 article for us.

1 Comment

Contribute to the conversation...

Yay! You've decided to leave a comment. That's fantastic. Please keep in mind that comments are moderated by the guidelines laid out in our comment policy. Let's have a personal and meaningful conversation and thanks for stopping by!