My Top Seven … Flawed Characters

This list comes to your wonderful eyeballs courtesy of Madame Annabel Smith, she of Whisky Charlie Foxtrot fame. She likes a sassy rogue, a cheeky devil, a lovable larrikin… you get the idea.

The lovable rogue is a literary trope in the form of a character, often from a dysfunctional or working-class upbringing, who tends to recklessly defy norms and social conventions but who still evokes empathy from the audience or other characters.
   – Wikipedia

So then she decided to list her top ten favourite lovable rogues from the world of fiction

Now when she first tweeted it she said “flawed characters”. And I said what a great idea, I will write a list too. Then I read her piece and she said “lovable rogues” and asked for people to add their favourites.

So back to my list. I cannot think of ten lovable rogues that I like let alone the top ten. I will read anything but I am notoriously picky about what I like and sometimes I like a book not because the characters are cool but because the writing is nice or something similar.

Annabel describes a flawed character thusly:

I’m actually rather fond of a good flawed character: people who do the wrong things for the right reasons, or even sometimes for the wrong reasons, but you can’t help liking them anyway. 
    – Annabel Smith

I seem to like writing them but I don’t seem to like reading about lovable rogues much – it’s far easier to say who I don’t like as a character, even if they are wonderfully crafted. So this is the list of seven characters who have flaws every which way that you look that I do like. No lovable rogues here.

So in no particular order of appreciation, here we go:

1.  Macbeth in Macbeth by Shakespeare

Yes, this image marries Annabel Smith’s keenness on Fassbender movies and my love of Macbeth.

There is flawed and then there is heavily hit you over the head with a cricket bat flawed. Macbeth is definitely the latter. So let me explain what I find fascinating about Macbeth here. This is a tragedy and in tradition hailing from the old Greek days of yore, tragedy is usually when the heroes die. Now Shakespeare was writing in a time where people still thought of protagonists as heroes and antagonists as villains. None of this anti-hero hero stuff for them.

In Macbeth, the protagonist is the villain. And it is done in such a way that it nearly slips one’s notice. Macbeth is a villain but he is also the key player on stage. To us, reading it perhaps this is why we find Shakespeare to be a great writer – to us he has subverted this idea seemingly under the noses of an Elizabethan audience.

But also equally not – we know a lot and can surmise a lot but it is hard to know exactly what people in Elizabethan times had come to expect of royalty, of how they thought about what was the norm in other countries. If they expected kings to be involved in murder and violence then it is a tragedy, it is the downfall of a hero. It is a tragedy to watch a man who has been lauded a hero fall from grace by tarnishing his soul this way.

So now, Macbeth has flaws and is both hero and villain. Throughout the play you are made well aware that he consistently chooses how he reacts to external circumstances and there are moments where you realise he would actually back down from violence and treason but he doesn’t because yet another external circumstance (such as Lady Macbeth egging him on) occurs and he loses the fight against it and gives in. Shakespeare is able to show the audience that Macbeth isn’t actually completely evil and by the end of the play he feels he must continue to do what he does, painting himself into a corner while trying to get out of it.

And don’t get me started on Lady Macbeth because we will be here all day. She is more concerned with their personal relationship – she is mad at him for backing down because it means he won’t keep his promises to her so she rails at him:

“What beast was ’t, then,
That made you break this enterprise to me?
When you durst do it, then you were a man;
And to be more than what you were, you would
Be so much more the man.”

…and then suddenly she realises that this murder plot is bigger than their relationship and she sees the changes in him and it is this sort of horror at what she has helped to create and what position she has placed him in: “Tis safer to be that which we destroy / Than by destruction dwell in doubtful joy.”.

This is also why I don’t like Romeo and Juliet – Macbeth intrigues me far more.

Ilinca Kiss’ portrayal of Lady Macbeth’s mental breakdown

2. The narrator, Sylvie & Bruno and Sylvie & Bruno Concluded by Lewis Carroll

Yes, he wrote more books. Yes, they are far more interesting than the Wonderland ones.

We lament that we cannot go home again, cannot be a little child once more, and Lewis Carroll’s works have enabled us to deny that reality momentarily, to indulge our dreams for one bright interval.
 – Jerome Bump, Introduction to The Rectory Magazine by Lewis Carroll (1975).

In these two novels we are led through the story by a narrator who has flights of fancy and is often away with the fairies to the point where he will be sitting in a train, looking at a little girl on the platform who suddenly becomes a fairy with whom he has a conversation for several pages before being jolted back to reality.

But interspersed with all this daydreaming is a plot about him travelling down to see a friend and suddenly being pulled into his friend’s efforts to woo a neighbour with whom he is in love. That’s the first book.

By Harry Furniss (en:Harry Furniss, 1854-1925) (Lewis Carroll: Sylvie and Bruno Concluded. (1893)) [Public domain], via Wikimedia Commons
By Harry Furniss (en:Harry Furniss, 1854-1925) (Lewis Carroll: Sylvie and Bruno Concluded. (1893)) [Public domain], via Wikimedia Commons
The second book has a starker reality – romance has won out for his two friends but now instead of being about the romantic nature of love, it’s about the compassionate side of love as the reality of the world he finds himself in includes the worry about catching the plague and wondering if his friend, a doctor with a charitable heart, will ever come back alive each time he goes out on call and if his newlywed wife will end up a young widow or not.

What I love about the narrator though is that his flaws are often to do with agency, as if he has none at all, he merely views the world(s) presented to him – he is a passive observer, things happen to him and they may or may not change him, yet the pacing of the story is good and surprisingly I do not feel the urge to hit him with a broom as I would if I met any such person in real life. AndI think the key to that is that I, as the reader, do get to see the other world that his friends do not (save for the odd occasion when the fairies actually do visit the real world) when he is being quiet and in the background. He is not afraid to question things, to ramble off philosophically (which often instigates fairies occurring in close proximity though as yet when I rant no portal to Fairyland opens up which makes me want to claim false advertising), to wonder at his own flaws (as viewed by Victorian society) and then also to accept them.

3. Moist von Lipwig, Discworld Series: Going Postal, Making Money & Raising Steam by Sir Terry Pratchett


“Steal five dollars and you’re a common thief. Steal thousands and you’re either the government or a hero.”
― Terry Pratchett, Going Postal

You can’t deny that Moist has flaws – he is a reformed con man, put by Vetinari to work for the good of the major city state Ankh-Morpork, rather than have him work against it. Vetinari does this sort of thing all the time by the way, being a rather savvy politician, who prefers to co-opt and use any great minds going about to his and the city’s advantage which sort of actually says a lot about how much Vetinari himself loves and is attached to the city – else why bother so  much?

But these are the books that I enjoyed in the series perhaps because they talked about the bits and pieces of world building, particularly both in a fantasy setting and in real life, that both readers and characters don’t often notice – how everything runs and works and needs to operate, about the problematic economics of running a fairly similar realistic world in a place where magic is possible and must be properly accounted for.

Had we been graced with Sir Terry Pratchett’s presence for a lot longer, I think we would have seen more of these books. Themes were alluded to in the first two including taxes and the civic projects that Vetinari had planned. Raising Steam was the last one and it isn’t the best one, it’s a quiet goodbye with it needing to not only address the advent of locomotion (once the Industrial Revolution with a mind of its own hits any world, it just keeps going, you cannot stop it) in Discworld but also the farewelling of characters and world.

But if you need to showcase these ways in which the city-state is run and keeps itself running and functional, who do you pick to help you do so? It has to be someone accessible to all levels of society, government, upper class, underworld, man in the street and it all boils down to Moist becoming one of Ankh-Morpork’s first public servants. But he gets bored easily, he thinks fast which can get him into trouble, he promises and has to deliver, and he relishes freedom. What makes Moist lucky is that he has an employer in Vetinari who recognises the danger of a bored mind and has probably already out calculated him in planning what projects and jobs to give him well in advance for years to keep him on his toes and keep him useful.

4. Uncle Podger (but also pretty much everyone else), Three Men In A Boat, J. K. Jerome

This book is a secret classic. It’s almost like an underground volume passed around by people because most people would never list it in a list of classic literature and when it was released the masses loved it but the critics panned it. You always stumble on to it quite by chance and quite by chance, this was on the shelf when I was growing up. And most of my relatives starting with my father all had their Uncle Podger moments so there were so many things to relate to.

In fact, when you read it, you do like all the characters, most of them vain, some of them rather crass or uncouth but nevertheless you like them. You recognise them for people you know or have seen – they seem real, they seem like real people you could know which is amazing given that we are talking about 19th Century Londoners being read about by a 20th Century South Asian girl. But that is how good and respectful and accurate J K Jerome is as a writer. To me, it read like a boy’s own adventure novel but without over the top racism, stereotyping and fantasy (though I will point out that he thinks most girls trying to boat on the river are nigh useless but that he also did go boating with his wife who was clearly capable of holding her own). The entire thing is fun and witty and very observant of other people which is why despite their flaws, despite Uncle Podger blaming everyone else and while you would not want to be involved in an Uncle Podger moment, you do find it hilarious.

“He would use a bit of string this time, and at the critical moment, when the old fool was leaning over the chair at an angle of forty-five, and trying to reach a point three inches beyond what was possible for him to reach, the string would slip, and down he would slide on to the piano, a really fine musical effect being produced by the suddenness with which his head and body struck all the notes at the same time. And Aunt Maria would say that she would not allow the children to stand round and hear such language.”
Jerome K. Jerome, Three Men in a Boat

And there are hints of how much the fun here also respects seriousness – the way J K Jerome discusses and addresses the girl in the river for example:

“…when evening fell and the grey twilight spread its dusky robe upon the waters, she stretched her arms out to the silent river that had known her sorrow and her joy. And the old river had taken her into its gentle arms, and had laid her weary head upon its bosom, and had hushed away the pain.”
   – Jerome K Jerome, Three Men In A Boat

And knowing that it is not a direct retelling of a trip but rather a mixed bag of occurrences from several similar boating trips curated together, you see how humour can be the lure by which you can hold a reader’s attention for a line or two to address a serious event before moving back out again very naturally and gently to another witticism.

5. Bertie Wooster, The entire Jeeves and Wooster series, P G Wodehouse

Now this is why P G Wodehouse is so clever – it is the intellectual snobbery of Jeeves versus the class snobbery of Wooster. That’s where the humour comes from. It plays into the idea that the upper classes are generally useless at anything which of course most people love to think. And Bertram Wooster is now a sort of poster boy for this idea.

And Bertram Wooster is a man with flaws – he has no sense of direction in his life but has an income not derived from a job so doesn’t seem to suffer from the existential dread that this would otherwise cause. He is buffeted from the usual ordeals of life and instead lives in dread of being set up with the wrong girl or harangued by his ever growing assortment of aunts. He wants to be left in peace to be a bachelor till he has his heart set on things otherwise and he is totally unsavvy as to how to operate when reality sets in beyond a certain parameter. He cannot adult and occasionally he cannot even teenager.

“There are moments, Jeeves, when one asks oneself, ‘Do trousers matter?'”
“The mood will pass, sir.”
P.G. Wodehouse, The Code of the Woosters

I am not a fan of a manchild in reality and what I think makes it a great series to read is that it is so much an exercise in schadenfreude: Bertram is Jeeves’ problem – someone else’s problem not yours. The reader doesn’t have to deal with Bertram and if it was just Bertram alone, then to a certain extent they would but no there is Jeeves instead. It’s Jeeves who has to basically more or less nanny him to the extent that even half his friends don’t come to him for help but want to avail themselves of Jeeves’ brain. What Jeeves gets out of it is the chance for a bit more control over what would usually occur in such a master – servant relationship and to be more stable and to be able to delight in the fact that he is looked up to in this way.  It’s two flawed characters finding a good balance in each other – the tension in the novels is added by outsiders, external circumstances and often Bertram’s reaction to said situation disrupting the nice routine the two have going and needing Jeeves to come in as a sort of human deus ex machina device.

“Bertie,” he said, “I want your advice.”

“Carry on.”

“At least, not your advice, because that wouldn’t be much good to anybody. I mean, you’re a pretty consummate old [prat], aren’t you? Not that I want to hurt your feelings, of course.”

“No, no, I see that.”

“What I wish you to do is put the whole thing to that fellow Jeeves of yours, and see what he suggests.”
P.G. Wodehouse

6. Peter/Audrey* in For Today I Am A Boy by Kim Fu

* Peter transitions to Audrey in the book so I am using the pronoun 'he' when it's Peter before identifying as female begins in the book and 'she' for the identity as Audrey after and 'Peter/Audrey" in general to signify that it's a transition story and the same character. It was the best option I could think of - "(s)he" and "they" didn't seem quite right in this context.

First off this is a book with a title that I would love to have. But Peter/Audrey has always, to me, been an authentic representation of a transgender character.

Peter doesn’t start out savvy as to what is going on and what is happening and what he should and should not be doing – it is something he (as Peter) has to learn, mostly through making a lot of mistakes where he (as Peter) is being micro-aggressive against others and Kim Fu does very well in illustrating the point that sometimes we bully so that we are not in turned caught out as not fitting in and then bullied ourselves – that we can turn on people out of such a sense of self-preservation and that in some cases like Peter/Audrey, it forms part of our growth – the guilt, the shame coming after it becoming so important in the process.

And that’s what I like about Peter/Audrey – she isn’t perfect, she just likes what she likes and then finds out it’s not quite right and then has to figure out if she can still do and behave the way she wants and how to navigate creating an authentic life for herself. And she gets it wrong quite often and messes up and goes backwards. Occasionally she is more reactive than proactive though this is mostly based on what is occurring in her life and there is a huge struggle always throughout between family and who she feels she actually is till the end.

But you can relate to all this, even the icky bits that make you cringe and the bits where you totally disagree with your actions and want to yell out and say “Not that!” as if she can hear you. Peter/Audrey is human. A great character but yes not perfect, very much flawed: too easily influenced and swayed, often not with a strong enough sense of self which has to be developed over time and is, and always trying to find a place to fit in rather than carving one out.

“The older you get, the more every trauma is the same trauma.”
Kim Fu, For Today I Am a Boy

7. Benjamin (& also Amy), Formaldehyde by Jane Rawson

This may or may not count as a cheat – I am not sure. I edited this book. I saw the draft versions. I saw both these characters. Paul is the main protagonist though you soon realise that by default the person everyone else is revolving around, whether they want to or not, is actually Amy. But more on that later.

Benjamin is actually female. A lot of the more initially obscure jokes in the book revolve around her (there was one I didn’t notice until after the book had been published). She does what she wants, she rarely has contact with friends and relatives as we are led to believe and not fitting in (for various reasons which I will not spoil for you), she keeps to herself. She also keeps information to herself, taking awhile before she shares it as she figures out what is happening. She feels no need, no requirement, to need anyone and she is happy to disappear the moment she feels she may get too involved in something.

Amy gets too involved and acts on how she feels, kickstarting the entire process off in the first place, having become pregnant (with Paul) while having an affair with another woman during her marriage. She too, does what she wants, with no regards for the consequences but initially doesn’t adopt the stance of keeping to herself until everything does seem to go pear shaped and she does then disappear, eventually reappearing gender transformed but leaving Paul with no mother and the initial problem of the novel that he runs into two decades later.

“I call an ambulance and hack my arm off below the elbow, taking care to tie-off first—I don’t want to die or anything overly dramatic.

I’m leaving my arm here for you. Suspend it in formaldehyde; suspend it in alcohol.”

 – Jane Rawson, Formaldehyde

What I like about both characters is how their flawed nature dictates their connection – how they can’t seem to escape each other, ending up even more connected to each other than before by the end of the novel, by the time Paul has figured out what has happened. How Paul starts taking on the same plans and habits as both of them in order to solve his own dilemma. How easy they find it to be fluid about their identities and ideas of themselves in order to get what they want – in both cases by the end, some peace and quiet to themselves with the minimum of fuss and drama.

So there you go: seven characters I like that I think are flawed. If I went on and tried to find ten, I would go mad writing and you reading.

But help my brain out because I would like to get to ten: please suggest characters in the comments and write your own list and let me know. I have a lot of books that do have flawed characters that I think are great but somehow are not quite in my top ten or that I just don’t like, such as those in Beloved or Handmaid’s Tale. I know not why – great books, great ideas, great characters but not quite my faves per se. Consider this now memefied and you tagged in it.

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