There’s a moment in the very first episode of Keeping Up With the Kardashians that foreshadows Bruce Jenner’s cultural trajectory. Flanked by his polished, supernaturally curvy stepdaughters and appearing a little adrift (pretty much his signature look on the series), Jenner hasn’t contributed a word to the family’s creepy postmortem of Kim’s recent sex-tape interview with Tyra Banks (the sex tape that helped launch the show). Right before the credits roll, though, Khloe quips to Kim, “You should’ve said, ‘Hey, Tyra, wait ’til you see Bruce’s sex tape.’ ” At this, the ladies burst into a chorus of not entirely kind cackling. Imagine Bruce, their laughter says, occupying the cutting edge of anything. No, Bruce is just their hapless stepdad, reduced to blurting upbeat or scoldy dad sounds from the edge of the frame. Little did they know that, six years later, Bruce would be the most intriguing member of the family—more intriguing than Kanye, North, Kim, and her internet-breaking bumper combined.
Jenner has indeed upstaged the entire Kardashian clan, the ultragroovy Wheaties-loving Olympic hero of one celebrity-spectacle era seeming to gear up to transform before our eyes into an even groovier transgender hero for a whole new media era—with all the blaring headlines and swirling cameras such a rollout entails. Then, on February 7, Jenner was involved in an accident in which his SUV struck a Lexus, causing the car to swerve into a Hummer. The driver of the Lexus was killed. Initial reports claimed the crash was caused by paparazzi, and while the LAPD has said photographers were not involved, close-up photos demonstrate their presence at the scene. You can literally follow the crash second by second.
The event felt like an intrusion of the real into a world of spectacle. And even as Jenner delayed both his already-taped exclusive interview with Diane Sawyer and the filming of his E! docu-series, expressing his concern for the victim’s family, his words had the tinny echo of a real sentiment filtered through layers and layers of artifice. But then, that’s the only way we’ve ever heard him. His family has performed for years in a clown show of their own design, in which self-conscious humans also falter and feel real pain and express their love. There have been marriages ending, others staged quickly in the face of family protest, an actual on-camera childbirth, the disappearance of one husband into crack addiction, the slide of a baby daddy into alcohol abuse and spasms of violence (and then out of it, maybe, based on the end of the past season). Critics of the Kardashians often complain of their ephemerality, but viewed another way, they may be our most substantive celebrities, enduring every imaginable major life event and the circus of celebrity in full view, in a kind of unprecedented performance of uncanny reality. Existing categories of human experience can’t accommodate this blurring of boundaries between authentic and fraudulent, absurd and grotesque, comic and catastrophic.
Are we peeking behind the curtains or a part of the show? At the very least, the crash will surely appear on Jenner’s new series—itself the apotheosis of his carefully laid plans to become the biggest explosion in the Kardashian armory of attention-seeking missiles. Before the accident, that mission was almost complete: A media frenzy has continued for months, unleashing a torrent of responses from tittering to dissecting to solemnly instructing the proper reaction to every minuscule change in Jenner’s appearance, every passing comment by his distant associates, every tiny clue as to what comes next. And ironically, just as a chorus of voices rises to defend Jenner, insisting that his privacy be respected and all speculation be halted in its tracks, there are reports that E! cameras will capture Jenner’s very private “journey” from start to finish. Suddenly, we’re reminded how fluid the term “privacy” can be among the Kardashian clan. The tight-lipped response by Jenner’s kids to his transformation now looks less like respectful silence and more like a way of pumping up suspense. Even in the wake of the crash, “Page Six” reported that “Bruce Jenner will reveal female name to Diane Sawyer,” while Radar Online claimed that both “the filming of the docu-series and the surgery will carry on.” In other words, not only won’t this very private matter be handled in a private way, it will be timed in accordance with media cycles and billed by the hour at union rates.
Such sophisticated media-flanking maneuvers make it harder to root for Jenner. After all, his charm has always relied on playing the accidental bystander in his ex-wife Kris’s fun house of horrors. Although he has dutifully bumbled his way through each new season of Kardashians, bungling his “We’re-besties-we’re-happy-it’s-all-good” lines with more than a whiff of contempt, he and his spawn have lately seemed less tolerant than ever of their matriarchal mastermind, who has trotted out every family secret under the sun for the sake of ratings, all the while wailing and tearing her hair over the no-fair impositions of the press and any acquaintances who’d dare to grab the media megaphone (and whose curated carnival reel mostly plays like a Möbius strip of selfie-taking and iPhone-beeping and TMZ-reading outrage, their televised lives a muted reverberation of the fuss being kicked up outside the compound walls).
Jenner’s upstaging might seem like the perfect karma for Kris, who may be the most openly manipulative character in TV history. But it’s still hard to believe that he finally escaped that airless, leopard-printed, throw-pillowed purgatory only to create his own living hell in its image. It also feels a little tragic: Wouldn’t we hope that he could go through this transition in private? What does it mean that he’s chosen not to? Some have even suggested that, having been surrounded by glossy, bossy, surgically perfected Jessica Rabbit–style femininity for so long, he couldn’t help but succumb, that Jenner was henpecked and emasculated and feminized by sparkling Kardashobots until they actually turned him into one of them!
But of course, that’s not how the transgender thing works, and maybe that’s something Jenner will help bring to light. Because with each close-up in a celebrity magazine, it becomes clearer how dramatically the former Olympian has come to embody our collective anxiety about masculinity—not to mention our curiosity, fear, and looming questions about transgender identification. A ’70s-era poster boy of wholesome manhood poised to become a woman right before our eyes, doing it in middle age and at the very center of the spotlight—in fact begging for the spotlight not to leave him even for a moment. You can almost hear a gaggle of smarmy producers whispering in his ear, telling him that by taking his private journey public he could become the compelling hero he never was as Kris’s sidekick. Their pitch may make them the deepest cynics of all, but they happen to be right: Thanks to Jenner, our long-held assumptions about gender suddenly look constructed. All we thought was solid glass ripples like water under a single pebble.
These ripples will be felt far and wide, whether we’re ready for them or not. But is Jenner himself up for the challenge? The Bruce we know from television is clumsy and a little corny, unable to connect with his family even when he’s at pains to emote. It’s hard to watch him and not wonder why our first transgender poster woman can’t be scripted and directed by Transparent’s Jill Soloway. Instead of clueless-dad fumbling, why can’t Jenner rattle off the rapid-fire one-liners of Laverne Cox’s character on Orange Is the New Black?
Well, because those are fictional characters. And as weird and staged and mercenary as the Kardashian dynasty has been over the years, Jenner is a real human being and, skeptics be damned, this transition may be the realest thing he’s ever done, maybe even realer than winning the Olympic decathlon in 1976—itself the ultimate athletic role-playing game, an arbitrary feat of ancient devising. Now, finally, the role is truly his. No longer content to play the far-out Olympian or the hapless dad or even the closeted eccentric with the French manicure, Jenner is going to play himself for the first time. Adrift for years on a sea of fake, Jenner just found his life raft, and he wants the whole world watching as he rows it into shore. But will he look heroic or just lost through our surreal mediated spyglass? It’s anybody’s guess.
*This article appears in the February 23, 2015 issue of New York Magazine.