 When Sasha Colby first appeared on season 15 of RuPaul's Drag Race, she was already being described as your favorite drag queen's favorite drag queen. And while that might sound like a pretty lofty title to live up to, it's also accurate because the former 2012 Miss Continental winner has more than two decades of drag performances under her gown already. Despite the lengthy list of trans women working in the drag industry and openly trans women competitor has yet to win the Drag Race flagship series, until Sasha did. And now that she's accomplished this remarkable feat, Sasha's finally getting the flowers she's always deserved. Beginning with her childhood in Hawaii, Sasha Keikooha formed a lifelong relationship with clothes as a means of gender expression and freedom. She also had some surprisingly unintentional helpers. As a kid, Sasha Colby was raised in a family of Jehovah's Witnesses, but that never stopped her parents from dressing her in tight little shorts that no other boy her age was wearing at the time. She once explained to Out Magazine, In elementary school, I was already a blonde kid in the middle of Hawaii. I had green eyes, pretty fair skin and was femme presenting. I felt like my parents unintentionally dressed me up very feminine and they didn't even realize it. Short shorts were only the beginning. As a kid, Sasha would try on different forms of female clothing, which then allowed her to access new realms of her own creativity. The first gender-affirming clothes she ever donned were her sister's negligee and bra. She described these moments of discovery telling out, From elementary to high school, I would come home and I would play in my sister's makeup because she would have it in the bathroom. So it was easy for me to just grab a little liner, put some mascara on, light a candle, put on music and I would lip-sync in front of the mirror for hours. Three hours from three to six a.m. By the early morning, Sasha's father would be banging on the bathroom door, pleading to be let in so that he could shower and get ready for work. Of course, there were also pop culture references that definitely played a part in helping Sasha come to terms with who she really was. Films like Mrs. Doubtfire and to Wong Fu, thanks for everything. Then she met her first trans woman in real life, her mom's hairdresser Tammy, a super tall, very loud queen who Sasha immediately gravitated towards as she began her own transitioning journey. Around that time, some of Sasha's friends took her to her first drag show at a local nightclub and she's been chasing the amazing feeling that evening instilled in her ever since. The house of Colby began not with Sasha but with another queen named Cassandra. Like Sasha, Cassandra is also a native Hawaiian and trans woman who Sasha encountered when she began sneaking her way into LGBTQ plus bars to catch her new favorite form of entertainment, drag shows. At the time, Sasha was around 18 years old and looking for a seasoned queen to pass on their maternal instincts as a drag mother. Most of the women Sasha met and asked wound up telling her no, but Cassandra was different. The moment these two met, there was an indescribable energy and they soon discovered that they shared a whole lot in common in terms of their history. When Sasha confided in Cassandra about her trans identity, she'd call from home, whispering on the phone so that her parents wouldn't hear. Learning from Cassandra gave Sasha the confidence and belief that she could carve out a normal life for herself as well. Soon afterwards, Cassandra adopted Sasha and the Colby family has only grown from there with Sasha adopting her own kids like former drag race contestant, Carrie Colby. Her relationship with Cassandra would also become all the motivation that Sasha needed to transition into a woman. Once that journey had begun, Sasha continued to express herself through fashion and style as she gained more confidence and experience. Then she began to hit the stage. 2005 was the very first time that Sasha competed in the Miss Continental Pageant. An annual drag queen event founded in 1980. During that first appearance, Sasha put on the first gown she ever worn, a piece that was handed down to her by none other than Cassandra. Cassandra wore that same dress when she won the Miss Universal Show Queen and all Sasha did was update the look by adding on a cool coat. While she might not have won the trophy that year, a short time later in 2012, she finally took on the crown in a performance that drag queens still talk about to this day. While Cassandra might have passed on all she knew about fashion and style, it was another individual who taught Sasha about makeup, her drag brother Preston. Sasha's always the first to admit that makeup is more or less the last frontier for her when it comes to her own sense of style. Simply put, glam isn't her strong suit. So she relies heavily on Preston's ideas when it comes designing her elaborate looks. Then there's her hair. In terms of inspiration, Sasha always likes to go back to the archetype of the beautiful, effortless hula girl. For most of her life, Sasha has always kept her hair long. But then, just before she was set to appear on Drag Race, she lost two family members. In an attempt to cleanse herself, she actually cut her hair to realize that she didn't need it to feel affirmed. The idea worked and Sasha immediately felt liberated. Then she prepared herself for the biggest stage of her career. Being the drag veteran that she is, Sasha Colby put a lot of thought behind how she would enter the workroom of Drag Race for the very first time. She looked to who she is as a person, a native Hawaiian, and then took on the persona of a powerful tribal warrior. The type of skirt she wore with this look is referred to as a mahalo and it's usually worn more often by men rather than women. So with this little touch, Sasha was reminding other queer Hawaiians that she's a master of both the masculine and the feminine. As for the tattoos that completed the look, they symbolized transformation, which for a trans woman like Sasha provided another powerful statement. When it came time to put on her first runway look for the series, Sasha found a 10-year-old gown made by a New York City-based designer named Gustavo Bustos, a piece that she previously wore the same year she won Miss Continental. As Sasha continued to survive cut after cut, there remained a sense of inevitability around her potential win. After all, she's already a legend and having killed it as much as she did this season, why shouldn't she win? Well, working against her was the sad fact that representation has always been something of a thorny issue for Drag Race. For years, the contestant pool was largely made up of cis gay men performing in drag as women. And while the production company behind the series never officially prohibited trans performers from competing, in 2018, RuPaul told The Guardian that he would probably not let trans women on the show, stating, "'You can identify as a woman and say you're transitioning, but it changes once you start changing your body.'" That led to a massive fan outcry leading to RuPaul eventually walking back on his comments. Since then, a number of openly trans contestants have appeared on Drag Race, but none of them ever won until Sasha Coolbie took home the crown at the end of this season. When asked to reflect on what winning this world-famous competition meant to her, Sasha told out, "'I've just been working so hard and never thought that anybody was watching or even noticed it. The amount of love that I've gotten has made me feel like my 20 years of work really meant something, that people are really watching.'" Winning RuPaul's Drag Race was all about seizing control of an opportunity for Sasha and accomplishing her wildest dreams. Now that she's done it and turned herself into a household name like never before, well, you can be sure that Sasha Coolbie won't be going anywhere anytime soon. Not now that she's finally arrived once and for all after 20 years of hard work and transformation. All right, everyone, that'll bring this latest before and after to a close. Thanks so much for watching today's video and before you head out, consider answering the following question. If you could be adopted by just one drag mother, who would you want it to be? Let me know which drag goddess you look up to in the comments down below. Otherwise, like, subscribe, and turn on your notifications to make sure you never miss a draw. My name's Kara. If you'd like to keep watching some of the most amazing transformation in celebrity culture, then stay tuned because coming up is a look into the transition of Dylan Mulvaney. I'll see you all next time. Bye. Dylan Mulvaney is a 26-year-old professional actress and comedian who grew up as a theater kid in San Diego, California. She also just happened to be born a boy. Dylan is known for about as long as she can remember that she identifies as female and as difficult as that made her childhood. It became an even bigger obstacle once she entered the theater industry and realized how gendered everything was. Simply put, producers were only willing to cast Dylan in male-oriented roles, which gave her very little wiggle room to expand into feminine characters. Mulvaney's 2022-er with the Broadway musical The Book of Mormon was where everything in her life began to change. When that production was halted, thanks to the onset of the pandemic, Dylan was finally able to turn her gaze inward and discover what it is she wanted out of life. While living back in her parents' house without a job, Dylan finally began to ask herself questions about gender that she had suppressed for so long. She explained to girl boss, I had never asked myself those dark questions because when I was four, I tried coming out to my mom as a girl, but it just wasn't a thing then. Being trans was very taboo. Then, during the pandemic, I was back at home living with my family and asking myself, Dylan, do you feel like a boy? Realizing the answer to that question was a resounding no, Dylan turned to TikTok and started producing comedy-style videos that included throwing a gender reveal party for herself. After getting her feet wet by creating a ton more content on the popular social media platform, a little over a year later, Dylan would inform her audience that she was officially a trans woman. Following that initial announcement in March of 2022, Dylan began documenting her transition the very next day. Over the course of 2022, Dylan Mulvaney created a series on TikTok. She called Days of Girlhood, in which she openly addressed topics like why she decided against changing her name while also documenting her experience with hormone replacement therapy and so much more. Initially, a lot of questions were raised over her decision to title the series Days of Girlhood rather than Days of Womanhood. So she broke down her reasoning in the following way. I didn't get to have Girlhood growing up on time as everyone else, and I'm now learning all the little things that little girls got to learn so long ago. I am going through many of the experiences of a child or a young adult, and that's why I don't feel really guilty about calling it that. For the most part, Dylan focused on sharing the highs of her transitioning experience, although she has also occasionally led us in on some of her lows as well. Such as that time in Uber driver made her feel wildly uncomfortable. But more often than not, her daily clips are chock full of optimism as well as humor from buying her first set of boobs to discovering how to use female sanitary products. Dylan never fails to share the good, the bad, and the ugly of her journey. By day 73, Dylan had come so far and made such inroads that even her own father was finally referring to her as his daughter for the first time. Then in December of 2022, Dylan took things to the next level. That was the day that she announced she was getting dropped off at the hospital to undergo facial feminization surgery. Now, for those of you who don't know, FFS encompasses a broad range of procedures that change the shape of the face to make it look more feminine. Examples include having the hairline move to create a smaller forehead, having lips and cheekbones augmented, or having the jaw and chin reshaped and resized. In late December 2022, Dylan began posting selfies from her hospital bed, letting us know that the process was over and that the time for healing had begun. She also wrote a personal note to her old face, saying, for now you are still a friend. Thank you for listening to my needs and taking one for the team. Please don't feel like you failed. I can assure it's me, it's not you. Since then, fans have continued to keep themselves updated on her recovery, like this clip from early January 2023, where Dylan reveals that she is literally the happiest she's ever been in her life. Later that month came the big moment, the face reveal. On January 27th, Dylan posted an epic two minute clip to TikTok. The features her channeling Audrey Hepburn in breakfast at Tiffany's and dancing to Swan Lake. Since then, Dylan has continued to see her popularity soar on social media, but that isn't to say that everything about her transition has gone smoothly. Today, Dylan Mulvaney has more than 10 million followers on TikTok, which is just an incredible number. Not only that, she walked her first red carpet at the Grammys earlier this year as well. But there are still a few things she hasn't been able to experience as a woman, like being kissed for the first time. During a conversation with People Magazine, the star opened up about her dating experiences since her transition, telling them, I'm getting a little impatient because especially when you're feeling yourself and even looking at the Grammys picture, I'm like, that's somebody who should not be single. But then you're like, wait, why is no one in the DMs? Well, now that Dylan identifies as queer, she believes her transition journey has given her a new opportunity to approach dating very differently than she has before. And this time, she wants to get things right. She continued to people, I can't wait for the day that I get to show people that a trans person can be in a healthy, happy relationship. According to her, what Dylan is looking for in a partner is someone who can make her laugh and help her take her mind off of all the important business decisions that she's making these days on a regular basis. Simply put, she can't wait to find someone she can just relax around and cuddle up next to on the couch. The only problem is that with how public Dylan is about her private life, it seems like most people she's talking to on dating apps aren't willing to put themselves out there as much as she is. Then again, with all the bank Dylan's been pulling in from advertising deals with companies like Mac, Neutrogena, Kate Spade, Nike, Bud Light, and so many more, I'm sure that she has enough on her plate to keep herself occupied until her ideal partner finally comes around. How long might it take Dylan to not only complete her transition but find the love of her life? We'll just have to wait and see. For now, this has been before and after. Thanks so much for watching today's video. And before you head out, consider answering the following question. What's the most personal revelation you've ever shared with others on social media? Let me know if there's something that you'd be willing to be so candid about like Dylan is in the comments down below. I know it can be scary. Just check out my personal channel and you'll see what I'm talking about. But otherwise, like, subscribe and turn on your notifications to make sure you never miss an episode. My name is Kara. If you enjoyed this look into Dylan Mulvaney's transition,