My World Of Flops is Nathan Rabin’s survey of books, television shows, musical releases, or other forms of entertainment that were financial flops, critical failures, or lack a substantial cult following.

Olympics champion, Wheaties box cover model, Can’t Stop The Music star, and reality-show dad Bruce Jenner’s transition into becoming Caitlyn Jenner was big news across the pop-culture spectrum. Particularly in the world of reality television, where Jenner’s children, stepchildren, and ex-wife Kris reign as royalty, but unlike British monarchs, the Kardashians do useful things like make quality sex tapes and popular iPhone apps. Jenner had been living his life on reality television for close to a decade when he transitioned and instantly became the most famous and ruthlessly scrutinized trans woman alive.

Part of the voyeuristic appeal of I Am Cait, Jenner’s talked-about but short-lived reality show, lies in seeing proud conservative Republican Jenner reconcile her awakening as a proud trans woman. Can she do so in a political mindset aligned with homophobic, transphobic conservatives who terrify voters with nightmare scenarios involving men in dresses sneaking into women’s bathrooms to sexually assault little girls? Can someone be both a powerful advocate for the trans community, and a proud supporter of the political enemies of the trans community? That is one of the central conflicts implicit in I Am Cait and Jenner’s persona as both an unlikely trans pioneer and an absurd example of unexamined white privilege.

To its credit, I Am Cait doesn’t just acknowledge progressive critiques of Jenner as someone whose incredible wealth and privilege has shielded her from the harsh realities of life, particularly involving the trans community. These socio-political issues are implemented into the show’s structure. I Am Cait is about its star learning what it means to be an out trans woman, but also what life is like for people, trans and otherwise, who live outside the bubble of fame and money and power where Jenner has long resided.

I Am Cait didn’t just aspire to be popular. It wanted to be a force for social good, not just engaging television. It would educate as well as entertain. The show’s visual aesthetic reflected its high-mindedness: The tone was independent film-earnest and sincere, full of muted colors, pretty scenery, copious wine-drinking, and tremblingly sensitive background music.

The show surrounded Jenner with impressive and accomplished trans women like professor and author Jenny Boylan and Gender Outlaw author Kate Bornstein, who identifies as gender-non-conforming. These remarkable human beings acted as mentors to Jenner, helping her navigate the tricky territory of coming out as a trans woman. I Am Cait surrounded its star with people who have spent their lives thinking and writing and talking about gender and sexuality and LGBTQ rights. As women like brassy, vivacious entertainers Candis Cayne and Chandi Moore help Jenner understand what life is like outside the magical castle of wealth and fame, it quickly became apparent that any of them would make for a better reality show subject than Jenner.

Jenner’s emergence as the world’s most famous trans woman is unexpected in part because she is conservative in more than just the political sense. Though eager to learn more about the LGBTQ community, Jenner clearly does not like change. She gravitates toward ritual and repetition, yet suddenly finds herself starting fresh while in her mid-60s.


There’s a riveting moment late in the first season when a nervous Jenner refuses to switch her long-time country club membership into Caitlyn’s name because she’s worried about the reaction to her transformation at the conservative club. To paraphrase the old Groucho Marx line, Jenner still wants to belong to a club that she suspects might not want someone like her—transgender—as a member. Otherwise, Jenner’s country club wants people exactly like her: rich, famous, conservative, and so averse to upsetting the establishment that they’d rather pretend to be someone they’re not than risk rejection. Jenner is intent on living out loud and shouting her truth from the mountaintops, but not to the point where it might make things uncomfortable at the country club.

If the show had connected the struggle of one incredible wealthy trans woman to use one specific locker room to the ongoing struggle of all trans people to use bathrooms that reflect their true gender identity, the show’s first season might have lived up to is potential. But I Am Cait isn’t that kind of show in the early going. Jenner professes to be deeply moved, to an almost life-changing degree, by so many of the stories she hears in the first season from trans children and teenagers that her declarations of being shaken to her very soul begin to feel arbitrary, more a default response to any emotional story than a sincere emotional reaction. But if I Am Cait overplays the uplift angle, there are moments throughout that are genuinely affecting. The relationship between Jenner and her 89-year-old mother, who is eager to understand her child despite her fierce conservative Christian convictions, is poignant and multi-dimensional. Jenner’s children and step-children are eager to understand her, but are also sensitive to the feelings of Kris Jenner, who understandably felt blindsided by her former partner’s transformation.

The first season of I Am Cait is a strange combination of earnest good intentions and pragmatic calculation. In its early days, I Am Cait never settles on a consistent tone beyond looking like what a Yankee Candle shop smells like. The show deserves credit for having a strong sense of social responsibility, for genuinely trying to make the world a better, more loving, and inclusive place. Yet in its rocky first season, those noble aspirations weigh it down.


In Jenner, I Am Cait has a heroine whose imperfections are alternately fascinating and maddening. Shy, self-conscious about her sexuality, and not inclined to self-reflection, she makes for an unlikely civil rights pioneer. On the first season of I Am Cait, that responsibility weighs heavily on the show and its star alike.

I Am Cait set out to give the issue of trans rights a familiar face the public could relate to. Jenner’s nervousness and fawn-like vulnerability are both understandable, but the wealth and privilege of Jenner’s life are harder to relate to. I Am Cait is about Jenner learning what life is like for her colleagues in the trans world, but it’s also about Jenner learning what life is like for people who aren’t rich and famous.

As a docu-series protagonist, Jenner proves aloof and unlikable. The first season ends with Jenner deciding that her transformation has not been celebrated enough, so she stages an elaborate name-change ceremony, complete with special guest singer Boy George. Jenner is surprised her trans pals haven’t had name-changing ceremonies themselves, so she says she’s having the ceremony for herself, but also for all the trans women not wealthy and narcissistic enough to spend a fortune celebrating their new name. Jenner’s “this is for all of us” posturing is disingenuous, since this is all about her, not a trans community she adores but does not yet understand.

Jenner is never more enraging than during a simultaneously fascinating and enraging sequence in the second season where she angrily tells her overwhelmingly progressive entourage that every conservative is a champion of everyone’s rights. She angrily proclaims that a Donald Trump presidency would be great for women, and that people like Ted Cruz and Mike Huckabee just want to create a wonderful economy so that every trans woman has a satisfying, well-paying job.


Jenner’s mentors are visibly aghast at her defense of transphobic politicians and a transphobic party, understandably. Brilliant intellects like Boylan and Bornstein have been trying to raise Jenner’s political and social consciousness. So when Jenner defensively lectures her intellectual superiors on how the world works, it’s dispiriting on multiple levels. It’s frustrating because what Jenner is saying is so clearly, transparently wrong. Yet it’s also frustrating because Jenner is not engaged in a spirited conversation with equals, but rather a condescending rant. The bullying tone of her monologue pisses off the women in her entourage as much as its content. Jenner smugly insists that people might have thought she’d change after the transition, that being a trans woman would make her more liberal, but that didn’t happen. Jenner somehow wants to grow and evolve without actually changing, which speaks to her privilege and entitlement.

At any given moment in I Am Cait, Jenner is the least likable, sympathetic, and interesting character onscreen. In its superior second season, I Am Cait regularly moves the spotlight from Cait onto other characters, and the results are liberating and fascinating. What other reality show would feature an intense but respectful debate about language, representation, appropriation, gender, and sexuality between legendary feminist academics like Bornstein and Boylan? Other more engaging characters include women like Ella, who at 18 already seems more mature and self-realized than the sixtysomething Jenner. Ella struggles with a father who wants to be publicly acknowledged as a supportive dad of a trans teen, despite being much less accepting in private. If the show had made it to a third season, perhaps it would have continued down the path of becoming an ensemble reality show about the lives of trans women, with Jenner still at the center but everyone afforded ample screen time and solo plot lines.

But fame got I Am Cait on the air. Fame made Jenner an instantly powerful and vulnerable and relentlessly scrutinized figure when she transitioned from Bruce to Caitlyn. Yet fame wasn’t enough to keep I Am Cait on the air beyond 16 episodes. Jenner’s own role on the show improved in the second season as she began focusing on integrating her old life and old self into her new existence as a trans woman. By the final episode, this complicated, poignantly lonely, and tricky figure even seems to have a changed a little, because she finally seems to realize that Ted Cruz is not every trans woman’s friend.


I Am Cait found itself creatively long after the world stopped paying attention. Jenner has spent much of the last decade in the white-hot glare of the spotlight, so she knows how fickle the public can be, and her well-intentioned and often fascinating reality show seems to have just missed the cultural zeitgeist. Jenner’s show was like the current political environment: messy, complicated, melodramatic, enraging, a battle between radically different ways of seeing the world and its problems, yet endlessly compelling all the same.

This might seem heretical given the nature of Jenner’s family’s fame, but not everything needs to be on television. Perhaps it would be best if the next stage in Jenner’s evolution involved seeing what life is like without a television crew filming her every move. That might prove liberating as well.

Failure, Fiasco or Secret Success: Secret Success