What’s Below Rock Bottom? The Roys Find Out In Chiantishire

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There comes a moment for each Roy child, where the clouds drift away, the obstacle-trees part and their path to the throne becomes crystal clear. After years of struggling alongside their siblings, one monumental accomplishment pushes them an inch further and they’re deluded into safety. In that moment, when they can almost taste success, once they’re comfortably bloated by confidence — that’s when Logan crushes them. Roman (Kieran Culkin) has been on the verge of that moment all season long.

Somehow, the guy known for unhinged acts, like masturbating on his office window, has figured out how to do his job unsupervised. Under Gerri’s (J. Smith-Cameron) tutelage, combined with his own determination to finally achieve some success, he’s rocketed up high on his father’s weekly “favorite child” rankings. In fact, he’s sitting so pretty at the top that he can envision a future where he rules Waystar Royco and does all the disturbing s**t of his dreams, like making Shiv his “sexy assistant.” 

But maybe Roman has forgotten: both Kendall and Siobhan have been where he now stands, riding high on big wins and next in line for the throne. And where did they find themselves soon after? In the darkest depths of rock bottom. Though he manages all sorts of memorable accomplishments this episode — flirting with a Contessa, sidling up beside Gerri’s boyfriend Laurie, and nailing the merits of a revised deal with GoJo — his glee is short-lived.

On the bright side, at least one good thing comes out of “Chiantishire”: Roman’s lifelong dream of f***ing his parents is one step closer to realization! Not an episode has gone by without the youngest Roy making a joke about getting f****ed by his father or entering his mother’s vagina, so naturally, the next step was whipping out his d**k in front of them. Or, at the very least airdropping a picture of it to his father. This is the epitome of a Freudian slip — in the midst of a board meeting where Roman successfully sells the team on considering a merger with GoJo, he makes a mistake he will never live down. A d**k pic meant for Gerri, with the caption “eat this,” goes instead to his father … who’s sitting less than six feet away.

We should’ve seen this coming. Chekov’s D**k Pic was mentioned earlier in the episode, when Gerri asked Roman to quit sending her such sensitive “items.” She’s been doing her best to reign him in all season, trying to set boundaries and focus on business rather than his very specific source of pleasure. Yet he continues getting comfortable in her office, sending unwanted d**k pics and obsessively clinging to her side (especially now that Laurie’s in the picture). Roman mistakenly attributes a tendency to self-destruct to Kendall, but it’s clearly a family disease. They’re all their worst enemy. 

During his meeting with Mattson, Roman tells his latest boy toy, “I am not telling you a single one of my weaknesses ever.” It’s a laughable assertion from Roman, who recklessly throws his trauma in everyone’s faces. He regularly walks into a room and screams his weaknesses to the heavens —  just last week he went on a tangent to Mattson about how he can’t piss in front of other men because “we don’t know why.” This week, Shiv tells her father that Roman’s always been weird about Gerri and “everyone knows it.” And as he sits across the table from his son, Logan’s disgust is rooted in knowing — how surprised is he, really? Is this just Roman being Roman, he wonders, or is his son more of a “sicko” than he realized? 

Roman’s rock bottom is simple: his father sees him and resents every ounce of what he perceives. If that disgust trumps whatever pride he felt just five minutes prior, then Roman’s dream of being CEO is officially dead in the water.

Extra special bonus points for every single expression that crossed Roman’s face after the death text was sent. I want those framed and put in the Louvre.

More bonus points for the best line of the night with pitch perfect awkward delivery: “I’m not a radical feminist, Dad, but I think perhaps we should not fire her for receiving pictures of my d**k.”

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