Which Rich Knucklehead Should Actually Be the Boss on Succession?

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Photo: HBO

If you haven’t been keeping up with HBO’s Succession, now would be a good time to catch up. As suggested by the show’s title, the plot quite literally hinges on a matter of succession: Which of media mogul Logan Roy’s children will take over his corporate empire? His second-oldest son, Kendall, seems to want it the most, but he’s no better off than his siblings when it comes to truly noxious personality traits. Not that you can really blame them, given the near-lethal cocktail of nature and nurture they all suffer.

After Sunday night’s episode, it’s all coming to a head: “I Went to Market” sets the stage for a potential coup against Logan — a no-confidence vote, engineered by Kendall, looms at the upcoming board meeting — so it’s the perfect moment to take stock of who would actually be best as CEO of this family-run entertainment conglomerate. In an ideal world, someone not utterly loathsome would swoop in to take control of the Roy media empire (and it would also involve a Billions crossover, but I digress). As things are, though, it’s a matter of making the best of a bad situation. Do any of these characters actually have what it takes to run Waystar Royko? Would they be pleasant to work for? Are they pleasant, period? From worst to best contenders, let’s take stock.

13. Greg

Photo: HBO

Succession offers up a very heavy dose of cringe comedy every week, and most of it usually comes from cousin Greg. In fairness, he’s not actually jockeying for control of the company — he just wants a job, really — but he’s certainly proved himself savvier than he seems. To be clear, that is not a high bar.

Pros
• He’s still young, so he might grow up to not be a total monster like the rest of his family.

• Despite being constantly terrorized by Tom, he is somehow still standing. (If anyone ever spoke to me the way Tom talks to Greg, I would start crying on the spot.)

• If you need anyone to reach the top shelf, Greg is your dude.

• His mother is played by Mary Birdsong, a.k.a. Deputy Kimball on Reno 911!, a.k.a. an angel, just in case you needed any further proof of Succession’s comedy bona fides.

Cons
• He’s still young, so he might grow up to be a total monster like the rest of his family.

• You cannot watch him do anything without getting cripplingly severe secondhand embarrassment.

12. Roman

Photo: HBO

Of the four Roy siblings, Roman is the wild card. He suggests going shirtless in order to brainstorm “shirts-off shit,” he talks about holding in his farts, and he does magic — no, wait, sorry, that last one is Gob Bluth on Arrested Development. The point being, Roman wants a leading role in the company, but he absolutely does not want to do any of the work that it would entail.

Pros
• He’s definitely the most gregarious Roy, and the least purposefully pretentious. He wears all of his awfulness pretty openly on his sleeve, which I’d say is better than trying to pretend otherwise.

• That Culkin energy!

Cons
• Literally the first minute he’s left alone, he jerks off onto his office window, which is an automatic DQ in my book.

• He’s the human equivalent of an online comments section, insomuch as I’m not sure when else I’ve heard the word “cuck” spoken out loud.

• I am not convinced that he knows anything about business. (In fairness, I’m not entirely sure what anyone really does on this show, but we see Kendall making some deals early on, which is enough TV wheeling and dealing for me.)

11. Connor

Photo: HBO

Had he not successfully pulled off the charity dinner in “Sad Sack Wasp Trap,” Connor would be sitting at spot No. 9 and Roman would be at No. 8, but the event went well enough, so here we are. As far as the company goes, Connor doesn’t seem particularly invested in what happens, but he’s interested enough to ask dear old dad for control over one of the company’s foundations, as well as to keep spending Roy money on his girlfriend, Willa, an escort with dreams of breaking into the arts.

Pros
• He can throw a party! Sure, he loses his mind when the butter pats are served frozen, but as someone who has worked these kinds of events, trust me: It really could have been worse.

• Butter pats aside, Connor seems relatively levelheaded, or at least the most so out of his siblings. He stays out of the in-fighting as much as possible, though who knows whether or not that’ll change.

• (Alan) Ruck Me Amadeus.mp3

Cons
• Staying out of family conflict has cast Connor as something of a milquetoast, and his sudden interest in business seems convenient rather than genuine. That said, we shouldn’t be surprised that he’s as flighty as the rest of his family.

• I cannot in good conscience fully endorse anyone who engages in so much PDA.

10. Logan

Photo: HBO

I agree with Kendall that Logan should take some time to convalesce, if not outright retire. But as this ranking is considering both worst- and best-case scenarios, I’d still rather have Logan in power than Roman & Co. Yes, Logan drove the company into massive debt and, yes, he’s a horrible, sexist, ornery old man, but he’s got ruling with an iron fist down to an art.

Pros
• The utter savagery required to tell your own child that he’s a disappointment is … a lot. But that’s probably good for business, right?

• He certainly knows what he’s doing more than Roman or Connor, both of whom he has rightly pegged as indolent and uncommitted, and nobody outside of the company seems to really trust his kids, either.

Cons
• He’s not a good father. I’m not certain that he actually cares about anyone. Accidentally or not, he hit Kendall’s son! At Thanksgiving!

• Two words: brain hemorrhage. From peeing in corners to forgetting to stop pouring coffee (and, lest we forget, briefly mistaking his daughter for his wife), he is clearly not well.

9. Stewy

Photo: HBO

For someone who seems to embody every finance-bro stereotype, Kendall’s old college buddy Stewy is weirdly unpredictable. Now on the board of Waystar — thanks to a deal struck to get the company out of massive debt — he’s clearly got his own agenda, which may not pay off the way Kendall wants it to.

Pros
• He is somehow not scared of Logan Roy, which is more than can be said of almost everyone else.

• While most Succession characters are sources of humor by how ridiculously they conduct themselves, Stewy is genuinely a funny guy.

• If you, like me, delight in yelling and pointing at the TV every time a New York theater fixture shows up, then you also probably cheered when Arian Moayed appeared on your screen.

Cons
• If there’s a drug test, Stewy will be out in a heartbeat.

• Funny does not a CEO make, and between his college-level behavior and his drug use, I wouldn’t trust Stewy with any more power than he already has, if that.

8. Lawrence

Photo: HBO

Lawrence is basically the son that Logan wishes Kendall were, insomuch as the blood in his veins seems to be just ice cold. But as things stand, he’s clearly a thorn in the Roys’ side. He hates pretty much all of them, and agreed to sell Vaulter to the company just to eat them alive from the inside. Sucks for Waystar, but hey, Lawrence is getting what he wants!

Pros
• The dude is ruthless! He’s like Littlefinger if Littlefinger didn’t care about not outright sneering at everyone.

• Unlike most characters on the show, he seems to know his worth.

• It’s worth pointing out that he’s a queer and POC character on a show that does not have a whole lot of either.

Cons
• He scares me a little bit; he might just be a little too cold.

• Conservatively speaking, digital media is a wild field.

7. Marcia

Photo: HBO

Though she’s only indirectly in the running, Marcia has served up so much Lady Macbeth-esque behavior already that she deserves a spot on the list. She is also, by far, the calmest person in the Roy family, which is a feat in and of itself.

Pros
• She is somehow the only character who has managed to escape any (unearned) ridicule. The Roy siblings make nasty comments about her behind her back, but to adapt an old schoolyard saying, it’s seeming an awful lot like she’s rubber and they’re glue.

• She knows exactly which strings to pull to get what she wants. I’d be frightened if I weren’t impressed. (Just kidding, I’m definitely both.) She also has an uncanny sixth sense for any movement against Logan, and how to cut it off.

Cons
• She’s too devoted to Logan. I love how much she seems to love him, given how rare genuine emotion is on this show, but at the same time, he is just not good news for the company anymore.

• Nevertheless, I’m willing to entertain the notion that she might have some ulterior motives. She uses her position in the family to get her son a job at the company, after all.

6. Gerri

Photo: HBO

Speaking of Lady Macbeth figures, Gerri is also one of the company’s best options. She doesn’t seem to want power for herself — nor do the Roys seem keen on giving it away — but she knows which way is up, and she’s at good at sniping her competition to get what she wants. Plus, you don’t cross J. Smith-Cameron if you know what’s good for you.

Pros
• She withstood being in the same room as Roman and Kendall for the shirtless brainstorming session, which is concrete evidence that she can weather anything.

• Regardless of who you want on the Waystar Iron Throne, it was delightful to see that she manipulated Greg into narcing on Tom. Not that I don’t love Tom (more on that later), but Gerri knows a weak link when she sees one.

• The Roy kids all come to her for advice, which is about as advantageous of a position as is possible.

Cons
• Some of that patented Roy untrustworthiness has rubbed off on her. We’ve seen Gerri outright lie a couple of times, each time without getting caught or suffering any consequences, which in retrospect might actually go in the “pros” column.

• I’m not positive that she won’t sway whichever way the wind is blowing when it comes to the balance of power, which isn’t ideal for a company leader.

5. Frank

Photo: HBO

Frank deserves some kind of medal for how much crap he’s put up with so far, which includes being cut from the company without any notice despite his years of service, then being brought back to essentially babysit Roman, and then having to deal with Roman and Kendall to boot. To that end, he’s kind of the bizarro Logan: He has a lot of experience with the company under his belt, but still seems to be a fundamentally decent person.

Pros
• For better or worse, he’s loyal to the company. If not meant for leadership, he’s at least someone that Kendall needs on his side if he really wants to take over.

• He’s played by Peter Friedman, who is one of the most comforting presences currently on TV. I’ve never met him, but I would trust him with my life.

Cons
• His skill at any kind of subterfuge is debatable, which can be a deadly flaw in a piranha pool like Waystar.

• Roman deeply resents having him around, though Roman isn’t really a huge fan of anyone.

4. Ewan

Photo: HBO

Okay, I know Ewan doesn’t really want anything to do with the company — or more specifically, with Logan — but hear me out on this one. He’s the Ron Swanson of the Roy family, in that he cannot abide chitchat or any other bullshit, and lives on a farm. Maybe that’s what they need!

Pros
• He really is a family man. As much as he may hate Logan and won’t stop ragging on him, he won’t let anyone else do it, either. It’d be sweet, if not for all that animosity between them.

• Nobody else in the family ever truly speaks their mind — besides Logan, of course — so it’s about time there was a counterbalance.

• I love how florid Ewan’s speech is, when he actually does open his mouth. “Pit of vipers” this, “nest of rats” that.

That’ll do, pig.

Cons
• He is terrifyingly no-nonsense. That 12-hour car ride with Greg on Thanksgiving is a thing of cringe beauty.

• He and Logan would end up killing each other if they stayed in the same space for more than a couple of hours at a time.

3. Shiv

Photo: HBO

Shiv comes off as the smart one, though whatever smarts she has come in exchange for losing some receptors for the feelings of others. Not that that’s a bad thing in a scenario like this, nor that it precludes her having any actual human emotions. The problem is just that the two aren’t in balance, which means that the people around her start to mistrust her, too.

Pros
• Like Kendall, Shiv is one of the few people on the show I actually believe holds a real job.

• She can spin almost anything, as is evidenced by the fact that she saves her political candidate despite a rather unfortunate picture (I will forever treasure the network discussion on how best to say “butthole” on TV) making its way to the press.

• Besides being the smart one, she also seems to be the one with her life the most in order. She’s not an outright mess like Roman, an inner mess like Kendall, or a middle-of-the-road mess like Connor. But that’s not to say she’s totally in the clear — it’s obvious that even her fiancé doesn’t trust her as much as he should.

Cons
• Though she tries to maintain her independence from the company, she’s also willing to leverage her social status to get what she wants. (To be fair, her hand in the matter is sometimes forced.)

• What’s the deal with Nate? Cut that man loose!

2. Kendall

Photo: HBO

Of the Roy siblings, Kendall is, of course, the best option — not just because he actually seems to have business acumen, but because he needs to step out of his father’s shadow and develop an identity beyond being a business bro. There’s something tragic about his story line thus far: He’s lost everything in his personal life due to his devotion to the company and an all-consuming need to earn his father’s approval, but the latter seems to be a lost cause, hence his hustling for a vote of no confidence. He deserves a win! Just, uh, not enough to place him at the top of this list.

Pros
• He works hard, which almost nobody else seems to do. And, again, I think I actually get what he does, at least in an abstract way.

• He’s a good dad — or at least, he tries to be — which can’t be said of his own father. This doesn’t, however, let him off the hook for how hung up he is on his ex-wife.

• Objectively the hottest Roy sibling.

Cons
• He’s a little too self-forgiving, as shown by how often he talks himself out of feeling bad and into being the good guy. For instance, when Kendall brings an ATN anchor as his date to the big charity event, he talks himself into thinking that it’s actually a date, and that he’s not being “That Guy” by bringing a employee. I hate to break it to you, buddy, but, as the lady says, you are That Guy.

• Every time he slips into bro talk, whatever goodwill I have for him rapidly drains away. There is really no bigger turnoff. (And, oof, when he psyches himself up by rapping along to the Beastie Boys — and when we figure out he’s doing it with noise-canceling headphones on, forcing his poor chauffeur to listen to him a cappella? I mean, I love it, but I also hate it. But I love it.)

1. Tom

Photo: HBO

Tom is the most demented character I’ve ever seen, and he belongs at the very top of Waystar. Unlike Shiv, he doesn’t come from money, which has manifested into a slightly manic attitude now that he’s reached the upper echelons of the rich. He’s worked too hard to fall out of favor with these people (and he really does seem completely devoted to Shiv), and though he may come off as a bit of a weasel, he’s at least doing his best to jockey for what he wants — namely, advancement. Matthew Macfadyen is doing god-tier work playing a character who could easily be a laughingstock (every Roy besides Shiv dismisses him on the basis of his background), to the point that, even if Tom weren’t obviously raring to go, I would have put him at the top of this list through the sheer strength of his performance alone. If there were a supercut of Tom Wamsgans, that’s what I’d use to sell people on this show.

Pros
• There’s something nice about knowing that he had to work his way up the ladder rather than having things handed to him on a silver platter.

• He is from the Midwest, and as such I am legally obligated to put him at the top of this list.

• Unlike almost everyone else in the series, Tom actually seems to have something of a moral compass, though it’s not not motivated by a certain sense of self-preservation.

• “Did you bitch me out, pig man?” is a gem.

Cons
• He is either not particularly socially aware, or far too socially aware. I can’t really tell which. Either way, he’s tapped directly into how best to needle or wheedle the people around him.

• Again, I would cry if anyone talked to me the way Tom talks to the people who work for him. But, God, I love watching it.

Which Rich Knucklehead Should Be the Boss on Succession?