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Why Do We Love The Sad Boy Of ‘Succession,’ Kendall Roy?

Succession is a show that constantly forces us to question our own moral compass. Should we root for certain characters? Should we laugh at certain jokes? Should puffer vests and turtlenecks look that good on the human frame?

But perhaps the greatest moral conundrum this HBO drama presents targets our baser instincts, our biological imperatives, our sexual preferences, the ramblings of our own inner hormone monster: Why do we find Succession’s resident sad boy, Kendall Roy, so damn attractive?

Kendall was the heir apparent in season one, a billionaire manic pixie dream boy who got hyped for board meetings by listening to the Beastie Boys and probably climaxed to the thought of “controlling the narrative.” Played by the multifaceted, unfairly talented Jeremy Strong, Kendall gave off mad sad fuccboi vibes. He was a Silicon Valley wannabe-John Keats, an Edgar Allan Poe raised in the Hamptons. He had ambition and drive, but no backbone to sustain them, stuttering through proposed takeovers and questioning big initiatives at the slightest hint of criticism from his overbearing, abusive father.

He was a daddy’s boy masquerading as the bold heir apparent to the Waystar Corp., a young-blood intent on reshaping his father’s legacy but unsure of how to go about it. Kendall Roy was the kind of Wall Street hotshot who’d gleefully swing his dick around the boardroom one second before apologizing when it inevitably slapped someone in the face the next.

And in season two, he only grew worse.

After launching a hostile takeover of his father’s company, Kendall, an embattled addict, rediscovered his love for nose candy – a doomed courtship that led him to seek drugs from a 20-something busboy during his sister’s wedding across the pond. The trip to score some powder ended with Kendall driving off into a ravine, the young waiter drowning, and the eldest Roy slipping back to the sanctuary of his family’s castle, into the arms of his manipulative father who used the whole affair to re-establish dominance over Kendall and the Waystar brand.

This season, we’ve watched as Kendall Roy descended further into Techno Gatsby madness, drowning his guilt and regret in model p*ssy – lots of it, just ask him – and more drugs. He’s limp-dicked his way through mergers and acquisitions, played errand boy to his father’s nastiest whims, cried at the kitchen sink of the family whose son he killed, shit the bed (literally) and, perhaps most embarrassing of all, performed a cringeworthy rap to honor his father’s fifty-year anniversary in the media business.

We should, in all fairness, hate Kendall Roy. So why then has he become a fan-favorite character on this show?

There’s the obvious attraction – Kendall Roy is the physical embodiment of an age-old literary trope, the sad, dark prince. He’s wealthy and tortured and burdened with great responsibility. He needs saving, his droopy face and puppy dog eyes tell us, and we can’t help but feel the compulsion to give this saddest of billionaire playboys a simple hug – he asks for one, quite often.

Self-loathing is a kink, even if we hate to admit it, and watching Kendall Roy spiral through his depression, wrapping himself in William Westmancott bespoke three pieces and snorting line after line of coke is the classiest, most aspirational form of self-destruction. Kendall isn’t wallowing in mud, he’s not sleeping in his car or panhandling on the street. He’s shitting himself in high thread count Egyptian cotton sheets and beelining for the roof of his company’s building in calfskin sneakers. His privileged form of despondence is almost enviable – it’s melancholic wealth porn we can’t help but watch.

It doesn’t help that Jeremy Strong is unconventionally swoon-worthy. Even when he showed up to the 2019 Emmys in an outfit almost assuredly stolen from his character’s wardrobe, the torch fans carry for him didn’t blow out. He walked the purple carpet looking like a 19th-century British butler haunting a decrepit mansion and social media confirmed that he could, indeed, still get it.

But the real appeal of Kendall Roy comes from this everyday man vibe he seems born with; a congenial, grounded personality that survived despite his elitist roots and cold upbringing. Kendall Roy may be, as he says, the human equivalent of a cock ring made from calamari, but he’s a calamari cock ring we could stomach having a beer with, a gloomy, gilded Byronic anti-hero. Kendall feels more approachable than his closed-off, stone-faced sister Shiv. He feels less unpredictable and combustible than his damaged younger brother Roman. And God, isn’t anyone better than Connor?

On a show where so many individuals consistently do so many reprehensible things and rarely ever feel guilt over them, Kendall Roy feels like an outlier. To see him suffer in season two, even as he contributes to the suffering of others, feels authentic and oddly uncomfortable on a show that’s built a reputation for dealing in uncomfortableness; a show where characters spout off about circle jerks and describe syphilis as the Myspace of STDs and trade soul-destroying barbs as an expressional form of familial love.

Maybe we gravitate towards Kendall Roy because we’d like to think, out of all the family members on this series — were we gifted with the same privilege and forced to suffer through the same callousness and unrelenting scrutiny — we’d turn out at least somewhat of a decent human being. Kendall Roy isn’t a good person, but he’s one of the better people on this show and isn’t it in our own hubris to want to believe the best in ourselves?

So yeah, maybe that’s it.

Or, as Roman might say, maybe we’re all just sick f*cks with a specific fetish for miserable fuccbois in fisherman beanies. Who knows?

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