Airing four close-to-perfect seasons between 2018 and 2023, Succession stands as easily one of the finest shows of the past decade or so. There’s little to suggest its reputation will do anything but grow as the years go along, too, as it’s the special kind of TV show that only seems to come around every so often. Masterfully acted and written, all the while being funny, tense, and ultimately kind of tragic, it’s easy to praise on just about every level.
One of the many great things Succession has to offer is memorable characters, with all the main ones being flawed, flawed, and compelling in all sorts of different ways. Most are affiliated with the powerful media/entertainment company Waystar RoyCo in some way, either by being employees or being related to the company’s aging CEO, Logan Roy, the man who, at one point, will need a successor. Succession mines both comedy and drama out of the fact that many of these prominent characters are out of touch and/or rather stupid at times, leading to numerous cringe-worthy and embarrassing moments. Here’s an attempt to determine how cringe-worthy the most prominent characters in the show are, taking into account the nine characters whose actors were credited with appearing in all (or almost all) 39 episodes of the show.
9. Gerri Kellman
Unlike the soon-to-be-mentioned main characters, Gerri Kellman was not in Succession’s pilot episode, instead becoming a series mainstay from episode 2 onwards, with J. Smith-Cameron receiving a credit for the 38 episodes that followed the pilot. She also stands out among all the soon-to-be-mentioned characters for being arguably the coolest, smartest, and least cringe-worthy of the bunch, though there is a disclaimer that comes with making such a statement.
Gerri might well be the smartest of the high-ranking officials at Waystar RoyCo, knowing how best to play the game and stay in everyone’s good books without stepping on anyone or making many enemies. She does this without seeming weak or becoming a target for other people to step on/overpower. But as for that disclaimer? Her “relationship” with Roman is odd, to say the least, though it can be viewed in different ways, depending on the viewer. Perhaps uncomfortable is a more appropriate descriptor than cringe-worthy, even when viewed unfavorably, what with both parties being adults and consenting and all.
8. Logan Roy
Logan Roy drives pretty much all the drama in Succession, and even if he might not be the main character going by screen time, he is arguably the show’s central character. Just about everyone else is defined by their relationship with him, and much of Succession is about who will succeed Logan as head of Waystar RoyCo, and the whole issue surrounding if and when he’ll actually decide to step down.
He’s manipulative, cruel, and cunning, but not invulnerable, with his age and ruthlessness letting him down every now and then. Not that such things matter most of the time, because his intimidation and wealth give him the sort of unlimited power that would make Palpatine blush. Logan can be described with many adjectives, but “cringe” probably isn’t one of them, outside some of the more uncomfortable things he does early in the show (the worst probably being when he was heavily medicated in season 1’s “Lifeboats” and seemed to mistake Shiv for his wife, in a mortifying scene).
7. Shiv Roy
Of Logan’s four children, Shiv arguably seems the most like her father, showcasing the same sort of ruthlessness as he does, though it takes her a little while to fully enter into the successor-related conflict. Season 1 sees her hovering around the outside of Waystar RoyCo, to some extent, and gradually being pulled into things as the show goes along.
Whether she lacks the killer instinct to be a true successor, or whether misogyny plays a role in preventing her from becoming a lead – or both, to some extent – is left up to viewer interpretation. Shiv’s a complex and difficult character, similar to Logan, but her gradual sense of neediness to attain the same power as her father potentially makes her a little closer to cringe. This is just the way it is. She doesn’t embarrass herself as much as her siblings might, but she’s still prone to doing some embarrassing and/or mildly stupid things. Plus, being engaged/married to Tom arguably makes one cringe by proxy.
6. Frank Vernon
It’s easy to overlook Frank Vernon, as he’s sometimes sort of like an even quieter and more unassuming Gerri, as far as high-ranking Waystar RoyCo employees go, but he’s not always as good at staying out of the way of crueler characters. Frank is kind of Logan’s go-to punching bag for a good portion of Succession, but even then, you have to admire his knack for surviving and never being fired for good.
Like a cockroach surviving a nuclear apocalypse, Frank Vernon just keeps on sticking around, riding the ups and downs (emphasis on the downs) that come with being a chief operations officer at the company. It’s not a position he keeps, but he hangs around in one capacity or another. It’s hard to call him too cringe-worthy, as he’s a bit of a loser while also being a survivor. It’s possible to both pity and slightly admire a character like Frank.
5. Roman Roy
One-time husband and apparent father Roman Roy is the youngest of all Logan’s children, and compared to his brothers, isn’t as frequently cringe-worthy. He has some awareness about the futility of the conflict others charge into, and that level of detachment does make him seem like he knows better a good deal of the time… even when he does nevertheless get involved in the war to be Logan’s successor.
Roman’s screw-ups might not be as frequent, but when they do happen, they are catastrophic. Case in point, one of the most awkward and squirm-inducing moments in Succession’s entire run comes near the end of season 3, when Roman accidentally sends his father a, let’s say, revealing picture. In a split-second, his chances of ever becoming head of Waystar RoyCo evaporate, and even if he succeeds in seeming too cool for everything in the majority of other episodes, the sexting debacle can’t be overlooked.
4. Connor Roy
Connor Roy is tricky, when it comes to Succession’s characters and their overall extent of cringiness, as he frequently says embarrassing things and generally acts in embarrassing ways, but also stays out of harm’s way much of the time. He’s treated as a bit of a joke by both the show and its characters, but he begins the series with some level of acceptance that he’ll never be Logan’s successor, and often just seems to be off doing his own thing.
Of course, when he’s doing his own thing, he still has the capacity to look ridiculous, but you have to admire someone who’s already learned the game is silly and that it’s best not to be too involved. He still remains a somewhat important character in the show, and has his fair share of cringe-inducing moments, even if they’re scarcely game-changing ones (like his eulogy at Lester McClintock’s funeral and his presidential aspirations).
3. Tom Wambsgans
One half of Succession’sworst but also lengthiest/most well-developed couple, Tom Wambsgans, was someone who did sort of win, at the end of the day… if you look at things a certain way; squinting may or may not also be required. He’s an outsider to the Roy family, marrying into it thanks to marrying Shiv and only being somewhat elevated by the fact that he is still above Greg, who’s subsequently targeted by Tom to prevent him from feeling like the lowest of the low.
So, Tom may end Succession in a better place than where he was at the start, and to his credit, eating Logan’s chicken near the end of season 2 was a baller move. But there are too many cringe-worthy moments along the way to count, from proposing to Shiv in a hospital, to being grilled over the Tomelette/Greggs line in a congressional hearing, to the thankfully off-screen debauchery at his bachelor party, Tom is a walking cringe-dispensing machine only somewhat redeemed by the fact that he finds occasional success, with some of that success conveniently being right at the show’s conclusion.
2. Greg Hirsch
To some, Greg may be endearingly awkward, and to others, his whole being may well be unbearable. Both camps will likely acknowledge his capacity to behave in incredibly cringe-inducing ways. Greg seems to lack knowledge of just about everything and anything, perhaps being the stupidest main character in the show as a result, and one who’s mostly likely the butt of other people’s jokes.
But Greg doesn’t need people to make jokes at his expense, because he’s already a joke. He stumbles into the Roy family’s horrible gravitational orbit early on and never leaves, starting out on the bottom rung, and maybe, if you’re feeling charitable, you could say he fumbles his way up one or two rungs over Succession’s four seasons. There’s an eight-minute video on YouTube that’s entirely made up of moments where Greg does or says something cringy… and the video only includes scenes from season 1. If it is to be sad that Greg is cringe, so it be, so it is.
- Kendall Roy
There are precious few episodes of Succession where “eldest boy” Kendall Roy doesn’t make a fool of himself. He’s at his “strongest,” relatively speaking, during the show’s earliest episodes, but even then, his introductory scene has him awkwardly rapping to himself in the backseat of a car, foreshadowing the “L to the OG” rap in season 2, which is unequivocally the most wonderfully cringe-inducing moment in the entire show (and that’s saying something).
His early attempts to act like his father generally fail, and then he enters a whole new kind of downward spiral following season 1’s sixth episode, where he entirely fails to overthrow Logan and never really recovers. Still, he continues trying to scheme and even force his way to the top, but it just becomes sadder and sadder to watch. It’s possible to pity Kendall and perhaps enjoy how hopelessly determined he is, despite failure after failure, but he’s also utterly embarrassing in just about every way, and his refusal to ever accept a loss just makes him ever more cringe-worthy as Succession goes along.
