12 Transgender Celebs That Broke All the Rules

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It’s an open secret that life isn’t easy for those who are transgender. In addition to fighting for acceptance of their gender identity, trans men and women are constantly fighting for everything from legal rights to basic human respect.

Some leaders in this fight are trans celebrities who have used their success and platform to improve the lives of trans people throughout the country and even throughout the world. But to achieve this success in the first place, these celebs had to first break all the rules.

Which trans celebs broke all the rules to make history? Keep reading to discover the answer!

Lana Wachowski and Lilly Wachowski

Lana Wachowski and Lilly Wachowski are the directors of The Matrix, and they also directed great movies like Speed Racer. Over on Netflix, the two made waves by creating the successful series Sense8. After these two transitioned, they became some of the most prominent trans voices in Hollywood. And on social media, Lily Wachowski caused a major stir by responding to Ivanka Trump and Elon Musk talking about taking “the red pill” (a reference to The Matrix) with a simple message: “F*** both of you.”

Chris Mosier

While not as well-known as Caitlyn Jenner, Chris Mosier is another trans celeb from the world of Olympic sports. Mosier has the distinction of being the first trans man to compete against other men during Olympic trials. And in terms of media attention, Mosier made history by being the first transgender man to appear in ESPN’s special Body Issue.

Caroline Cossey

Sometimes, trans celebrities end up making history in ways even they didn’t expect. For example, Caroline Cossey is most famous for starring in a bit role in the James Bond movie For Your Eyes Only. British tabloids ended up outing her as a trans woman, and Cossey responded by leading the fight for trans rights in the United Kingdom and becoming the first trans model to pose for Playboy. Plus, while the studio casting a trans person as an extra was not intentional, transphobes now have to reckon with the fact that the ultimate macho man, James Bond, was attracted to a trans woman!

Caitlyn Jenner

Caitlyn Jenner’s right-wing politics in recent years have lost her quite a few of the fans she once had. However, nobody can deny that, as an Olympic gold medalist turned trans woman, Jenner is one of the most famous trans celebs in the world, and she helped to normalize transitioning for countless people who would other struggle with their gender identity.

Asia Kate Dillon

Asia Kate Dillon previously starred in the third John Wick movie and currently stars in Billions. Dillon has the distinction of being the first nonbinary star to play a role in a major American TV show, and they helped more people become aware of the importance of “they/them” pronouns, without which many people would be unable to better explore their gender identity.

Andreja Pejić

The stunning Andreja Pejić has an interesting distinction in the world of modeling: she has modeled for both men and women’s clothing! She also made history by being the first transgender to get profiled by Vogue. Between appearing on the covers of magazines like Elle and GQ and appearing as a guest judge on Britain’s Top Model, it looks like she won’t stop until she is a household name.

Billy Tipton

While Billy Tipton was alive, nobody knew this iconic jazz pianist was transgender. After his death, though, family members discovered that Tipton was assigned female at birth but performed around the country as a jazz star, making Tipton one of the earliest-known transgender celebrities.

Candis Cayne

Candis Cayne is a celeb that knows what it’s like to explore gender in baby steps. The star previously performed in drag before fully transitioning, later making appearances in various Ru Paul projects. However, what really makes Cayne notable is that she landed a role on the show Dirty Sexy Money, becoming the first trans character on American primetime television.

Chaz Bono

Due to being the son of Sonny Bono and Cher, Chaz Bono was always destined for a life of media scrutiny. This meant tabloids outing her as a lesbian before transitioning, and after the transition, Bono made the most of the press attention by advocating for LGBTQ+ rights. Between discussing his story in a 2011 documentary and then appearing on Dancing With the Stars, Bono has done more than most celebs to normalize embracing who you really are.

Christine Jorgensen

Christine Jorgensen has the honor of being the first recorded person to ever undergo sexual reassignment surgery. This World War II veteran used the media attention she received to campaign for trans rights and acceptance, and her popularity as a performer and actress meant that many fans were receptive to her message.

Laverne Cox

While there are many trans celebrities, none are as famous as Laverne Cox. She was one of the breakout stars of Orange Is the New Black, and her amazing performance led Cox to become the first recorded trans person to be nominated for an Emmy in acting. Eventually, Cox starred in Doubt, becoming the first trans star with a regular role on broadcast television. If that’s not enough, she is a prominent trans activist who fights for LGBTQ+ rights.

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