Every character on Succession, ranked by how despicable they are

On this most wonderful HBO show, who's the least wonderful of them all?

Every character on Succession, ranked by how despicable they are
Images courtesy of HBO Max Graphic: Libby McGuire

To even ask who the most loathsome character on Succession is feels like a fool’s errand. The entire structure of every episode (and entire storylines in every season) have depended on the feuding and dueling ways in which each character’s brand of horrible behavior tips the scales any which way. Sometimes Shiv’s scheming feels more insidious than cousin Greg’s willful maneuvering of his own incompetence and feigned ignorance. And other times Ken’s woe-is-me toxicity feels like no match for his father’s psychological torture. You could flip a coin and still find yourself unable to choose between all of their many faults.

For make no mistake: These are all horrid, horrid people, the kind who often get so caught up in their own personal spats that they forget that the choices they make affect thousands (if not millions) of people around them. After all, what makes this Emmy-winning drama so resonant in this third decade of the 21st century is the way it reminds us that capitalism has bred its own kind of gentry—royalty, even. This is the Shakespearean drama they (and we) deserve, full of as many Richard IIIs as Iagos, as many Lady Macbeths as King Lears.

With the fourth season of the show set to premiere on March 26, let’s do our best to nail down the worst of the worst. That said, feel free to bicker away at this arbitrary ranking which, for our purposes, includes only the innermost Roy circle when it comes to family and business. (Sorry, Willa: We still have trouble thinking of you as a real Roy.)

Succession Season 4 | Official Teaser Trailer | HBO
LEAST LOATHSOME: Gerri Kellman
Gerri and Roman Have An Understanding | Succession | HBO

It is a testament to J. Smith Cameron that we never once considered ranking solid and reliable Gerri higher up. It’s not just that this bureaucratic hawk of a corporate woman leads with a kind of velvet glove even when she’s stabbing her colleagues (lover, even!) with a sharp knife in the name of stability (and profits, no doubt). It’s that she seems so self-possessed when doing so. Gerri is uncannily immune to the fickle nature of the Roy clan, Logan and Roman included. She’s ballast as storms (political, financial, and familial) swirl all around her. No one else in Succession feels like they come out unscathed as much as Gerri, who’s clearly mastered the art of letting corporate greed wash all over (and maybe even through) her.Also, give or take a Marcia, she really does feel like someone we would enjoy spending a lunch date with. Again, that probably says more about J. Smith Cameron than Gerri herself, but it’s undeniable the way the Emmy-nominated actor brings a honeyed sweetness to even Gerri’s most craven moves.

Greg Hirsch
How NOT to Negotiate with Logan Roy | Succession | HBO Max

Sometimes being a fool is the easiest way of letting yourself off the hook. Cousin Greg has spent the better part of three seasons being the stooge of the family. At first, that truly felt like an apt description for this tallest of rich boy muppets, with Nicholas Braun’s awkward posture serving as shorthand for the way Greg saw himself as an ill-fitting match whenever he was in the presence of his more openly scheming cousins (and uncle). Yet behind those gritted grimaces and gullible guffaws (seriously, Greg is peak cringe) was as unscrupulous a corporate guy as you could find. Don’t let him fool you; he’s been climbing up in ways that make you think he’s been merely failing upwards. Are we being too lenient in leaving him this far down because he is so obviously driven by survival rather than the loftier ambitions which dictate how the rest of his family operates? Perhaps. But then, he has such stiff competition he should be happy continuing to be underestimated. Who knows, come next year he may have climbed a couple more steps and perched himself higher up in Waystar RoyCo and on this list alike.

Tom Wambsgans
Tom & Cousin Greg’s Love Hate Bromance | Succession | HBO Max

Like Cousin Greg, there’s a way in which Tom moves through the world with such fumbling ease that it’s hard to recognize how much Machiavellian maneuvering is going on. (Is it a tall thing?) In any case, the way Jesse Armstrong and his writing team have structured Tom’s storylines means we haven’t really seen how his sausage gets made. We know he turned on the “bigot spigot” enough to get himself a nice Forbes writeup, but his business machinations more often take place off stage which is why, like his wife Shiv, we’re sometimes left wondering where and how Tom’s ambitious careerism fits in alongside her more hostile approach to getting stuff done. There’s an argument to be made that, especially with his running of ATN and the way he helped cover up the sexual scandals in the cruise division (talk about an eclectic business trajectory!), Tom may well bear the brunt of a lot of actual harm.Tom’s loathsomeness may not be so open or explicit. (He is nothing if not the sweetest husband Shiv could ever hope to find, the closest Succession gets to giving us a “nice guy.”) But that doesn’t mean it’s not there; he’s someone who’s been driven to be more of an opportunist with every new family crisis. And, as the season-three finale taught us, he really shouldn’t be underestimated.

Roman Roy
Succession: Roman Roy Is That Guy | HBO

Honestly, the fact that Kieran Culkin has made Roman such an entertaining figure makes assessing him in the context of this list hard. That is, perhaps, the point in any and all attempts to examine the role of humor in the show as a whole. After all, every time we giggle our way through Roman’s latest fuck-up (or his outrageously childish outbursts), the show all but demands we either feel complicit when we end up rooting for him, given that his entire thing is not caring about anyone other than himself (and, okay, maybe Gerri sometimes), or that we sit back and laugh at him and thus excuse him somewhat with our amusement. What makes us give Roman a little more leeway than, say, his sister, is the way he wears his loathsomeness like a badge of pride. Give or take a dick-pic moment, you’re hard-pressed to find any time when Roman feels any shame. He is unapologetic about his own wants and his baldfaced ambition, not to mention entitlement. Sure, that often makes him look like a spoiled rich kid (which he is) but there’s something admirable about such shamelessness.

Shiv Roy
Succession: Logan & Shiv (Season 2 Episode 1 Clip) | HBO

“I was only stealing so that I could win.” That line, uttered by Shiv when explaining why she’d been cheating at Monopoly in the season-three finale explains so much about how the Roy sister understands her own machinations. For Shiv, the means almost always justify the ends. Sure, she’d like to think of herself as having a clear moral conscience (maybe even the only moral conscience in her family!) but she also knows that such purity isn’t just a weakness; it’s an impossibility in a world driven and run by the likes of Logan, Kendall, and, yes, even Roman. One has to get dirty every once in a while. And one has to capitulate sometimes. If Shiv’s see-sawing moral standing threatens her ability to sit atop her high horse, that doesn’t stop her from still thinking herself immune to the grimy mind and political games her siblings and father (and husband!) play. Therein lies the way in which Shiv hopscotches her way past Tom and Roman. It’s one thing to say the right hand doesn’t know what the left hand does, but to suggest so when both hands are doing the exact same thing only in different circles … well, that’s just utterly loathsome.

Kendall Roy
Kendall Tries Negotiating With Logan | Succession | HBO

Did you expect Ken to be further up? It really is a race to the bottom with this family. And on any given day, this entire ranking could be reshuffled and we’d still find reason to find Ken more or less loathsome than his siblings. He is, like Shiv, insistent on thinking himself different from his father. There’s an Oedipal thing to the entire dynamic, sure. But Ken is still so much a little kid wanting daddy to tell him he did a good job that he sometimes wails and tantrums himself into the messiest of situations. This past season, thinking himself a white knight of sorts (if not an outright martyr who, did you hear, Vanity Fair wanted for a thing?) made him all the more insufferable. Which, you have to admit, was already a tall order. We all still shudder from his rapping days.Few others on this list are so cavalier as to create and nurture media PR crises to benefit themselves and score meager points in a family spat. Ken’s loathsomeness may come down to his crippling narcissism, but that doesn’t make it any less palatable. But also, he may be the only one in the Roy clan who’s able to feel anything remotely resembling guilt. Even in his most ill-conceived plots there’s a streak of sadness that runs through him, a pathos that ultimately makes him look that much more pathetic.

Connor Roy
Succession: (Season 2 Episode 8 Clip) | HBO

This may be controversial given that the eldest Roy is (how shall we put this?) not really that interesting. Connor may not get the melancholy tragedy of a Ken or the scheming ways of a Shiv—he doesn’t even get the dick pic quippy ways of one Roman. He often feels like the forgotten Roy. Which makes his entitlement all the more brazen and abrasive. Over the course of three seasons, he’s been turned into a perfect distillation of millionaire hubris where his utter lack of self-awareness—not to mention his unwavering belief that he is the smartest person in the room, not because he’s intelligent but because his words should carry more weight than others—has calcified into a terrifying figure that feels all too real in contemporary American politics.His siblings may be fighting over corporate scraps, and his father may be playing 3D chess, but Connor’s decision to gun for the presidency (however big of a folly that may be) shows precisely the level of loathsome he aspires to be. (Also, anyone who encourages and cuts down Willa with such ease deserves to be understood as utterly devoid of any redeeming qualities.)

 
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