Caitlyn Jenner’s Whirlwind 2 Years Since Coming Out as Transgender

by Elliott Smith 8:32 AM PDT, April 21, 2017
Playing Caitlyn Jenner’s Whirlwind 2 Years Since Coming Out as Transgender

When Caitlyn Jenner first sat down with ABC’s Diane Sawyer two years ago to reveal that she is a transgender woman, the revelation became part of the national conversation, given Jenner’s stature as an Olympic hero and, in later years, as the kindly patriarch of the Kardashian-Jenner clan on TV.

“For all intents and purposes, I am a woman,” she told Sawyer just moments into their highly watched interview, later adding: “What I’m doing is going to do some good. And we’re going to change the world.”

From that moment on, Jenner started living an authentic life that’s included high-profile magazine covers and a reality series documenting her transition, an unexpected connection to Amazon’s Transparent, which included a narrative similar to Jenner’s real-life journey, and controversy over Jenner’s politics and level of fame as it relates to the transgender community came into question.

“I really wanted it to not just be about me,” Jenner told ET one year after coming out. “I wanted it about this community and about the struggles and the difficulties, and to help people understand what being gender dysphoric, transgender -- whatever you want to call it -- is.”

On the two-year anniversary of that exclusive interview, Jenner will once again talk with Sawyer on a special edition of 20/20 (airing Friday, April 21 at 10 p.m. ET/PT) about the reality of her life since transitioning -- and the impact that she’s had.

Ahead of that conversation, ET looks back on what Jenner’s done in those two years:

Memoir: The Secrets of My Life

Some of the timing around the 20/20 appearance ties into the release of Jenner’s long-awaited memoir, The Secrets of My Life, which is scheduled to hit stores on April 25. According to Jenner, the book chronicles her “journey from Bruce to Caitlyn, and her brave transition into womanhood,” apparently pulling no punches when it comes to her surgeries and her relationship with Kris Jenner, who is reportedly miffed at how she is portrayed.

Docu-series: I Am Cait

Shortly after revealing herself as transgender, Jenner announced I Am Cait, an eight-part documentary series on E! that explored her transition and the effects it had on family and friends. The show premiered in July 2015 and served as an eye-opener for many viewers, who might have been previously unaware of transgender issues. The Hollywood Reporter called the show “surprisingly thoughtful if undeniably self-serving.” After two seasons, however, I Am Cait was canceled.

Scripted TV: Transparent

In a case of life imitating art, Jenner found herself with a cameo role on the season three premiere of the TV series Transparent, which revolves around family patriarch Maura Pfefferman (Jeffrey Tambor), who comes out as a transgender woman to her ex-wife and three kids. Jenner told ET at the time that her role, which was part of a dream sequence, “was so simple really,” she said. “My lines were already written! Doing reality TV, we have no script -- and it was great to work with such talented actors.”

Magazine Covers: Vanity Fair and Sports Illustrated

After coming out, Jenner appeared on the cover of Vanity Fair, shot by acclaimed photographer Annie Leibovitz with the headline “Call Me Caitlyn,” making her the first transgender woman to appear on the cover of that magazine. In June 2016, she appeared wearing her Olympic gold medal on the cover of Sports Illustrated, for an article in which she reflected on the 40th anniversary of her decathlon triumph and the struggles she felt at the time. “This woman was living inside me, all my life, and it reached the point where I had to let her live and put Bruce inside,” she told the magazine. She also appeared on Glamour’s Women of the Year issue and Advocate.


Jenner’s path over the course of these last two years hasn’t always been smooth. She was involved in a tragic multi-car crash in 2015 that killed a woman in California and led to several legal cases and settlements. Jenner’s political views have also come under scrutiny, as her Republican leanings have traditionally not lined up with the LGBT community. “It was easy to come out as trans, it was harder to come out as Republican,” she said at the 2016 Republican National Convention.

Endorsements: MAC Cosmetics and H&M

It would make sense that forward-thinking companies would want to pair up with Jenner, and she has been able to earn several endorsements. Jenner joined forces with MAC Cosmetics in February 2016 to create a signature shade of lipstick, “Finally Free,” with all proceeds going to the MAC AIDS Fund Transgender Initiative. Later in 2016, Jenner was named by H&M as the face of the brand’s sportswear line, with the brand telling ET, “We want to illustrate that everything is possible -- in sports, and in life.”


The way Jenner forged her path earned her admiration and acclaim from several groups. In 2015, she was honored by Time, Glamour, Entertainment Weekly, Out and The Advocate. In addition, she received the Arthur Ashe Courage Award during the 2015 ESPY Awards, where she delivered a powerful speech to an audience of sports luminaries and celebrities, in addition to the millions watching on TV. “I know I’m clear with my responsibility going forward: To tell my story the right way, for me,” she said. “To keep learning. To do whatever I can to reshape the landscape of how trans issues are viewed, how trans people are treated.”