December 28, 2016 2:15 PM EST

It’s become a meme, as 2016 winds down, to refer to the past 12 months as uniquely bad. The refrain comes up often but especially loudly on the occasion of a celebrity’s death. This week’s twin losses of pop singer George Michael and actor-writer Carrie Fisher had a special sort of sting — coming as they did at the end of a year in which several culture-shaking figures died. This was the deflating, cruel punch line. After all, Michael and Fisher weren’t just entertainers. Both used their fame to critique fame — a repressive system that kept their real selves from the world. They were born to be stars and, as if deciding that’d be too simple, they chose instead to question the very nature of stardom.

Michael was, with Prince, Michael Jackson, and Madonna, among the defining stars of the 1980s: his debut solo album Faith, released after a successful stint as half of the duo Wham!, provided the sort of career-sustaining ignition that his contemporaries enjoyed with breakthroughs like 1999, Off the Wall or Like a Virgin. Instead, Michael decided to follow up his ascent with a second act as subversive as it was effectively entertaining: the video for his song “Freedom ’90,” released just three years after Faith, depicted supermodels taking part in the destruction of emblems from the Faith era, including Michael’s jukebox and leather jacket.

The whole “Freedom ’90” exercise might have come across as tediously on the nose as performances of being “over” stardom can tend to be. Instead, it’s both virtuosic and ambiguous, yielding more to chew on than most videos of its era or ours. Michael was telling us, in a beautifully crafted song, that he was uncomfortable with fame, and he was opting out of appearing in the video entirely. But the people appearing on-screen are the perfect embodiments of 1980s and ’90s image culture and fame obsession. Michael may have been conflicted about fame, but he wasn’t quite through with it.

There’s an impulse on viewers’ parts to dismiss the star’s struggle — these people live, after all, privileged lives. But Michael’s probing the perks and challenges of celebrity, its sheen and the ways in which it redefines life, was more than simple whining. It was a project undertaken by both a curious mind and a songwriter and voice to back it up. Michael’s later life, as an out gay man in public life, felt similarly like a subversive project simply for the fact of its happening at all. Michael seemed, perpetually, far less troubled about endless scandals than did the media doing the reporting. He told Oprah Winfrey he wasn’t interested in selling music to homophobes, even as the correct answer for his record label would have been that he wanted to sell music to everyone. His willingness to be guilelessly himself was startling simply because we were accustomed to celebrities dissembling in order to preserve their market-tested likability.

Fisher, similarly, refused to be anything so simple as just a star. Famous since her early life as the daughter of superstars Debbie Reynolds and Eddie Fisher and cast as a teen in Star Wars, Fisher had the makings of a blandly popular Hollywood icon. Instead, she chose to publicize that which most stars try to hide. She wrote candidly about her mental illness and substance issues, as well as her mixed feelings about the sexualization of Princess Leia — all of these the sorts of things stars, and women in particular, aren’t supposed to say. She used her moments in the spotlight to puncture the fixed ideas of Hollywood. During the recent Star Wars: The Force Awakens publicity tour, she brought along her dog Gary and seemed to be undertaking a project of her own to expose just how silly daytime talk shows are. (She succeeded.) Fisher’s speaking her mind helped destigmatize addiction and mental illness; it also helped put eloquently into words quite how shallow so much of the Hollywood apparatus really is.

Celebrities are supposed to be certain things: well-behaved. Grateful for the opportunity (as made clear by a letter from Frank Sinatra scolding Michael that has been lately, for whatever reason, irksomely buzzing around social media). Ultimately nice, polite and good-humored. The thing is, where in those traits does art sneak in? It is impossible to put one’s work and oneself forward to be meaningfully understood and to be uncontroversially likable at the same time?

Michael and Fisher chose, in their own ways, to operate outside of established rules governing how stars should behave, and surely lost fans in the process. But those willing to go along with them found ample rewards. In a world now overrun with aspiring Instagram models and YouTube superstars loudly insisting that they deserve the gift of fame, Michael and Fisher — using their repute to advance complicated and messily real selfhood — feel more out-of-vogue than ever. And at the end of year during which the apparatus of fame has elevated one of its most unquestioning, incurious practitioners to the presidency, the loss of two people cannily aware of the system’s ability to warp the individual resonates too painfully.

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