Shady Characters


Here is a literary exercise which might help illuminate a dilemma nagging my real life. When we are done with the exercise, hopefully, you can give me counsel.

Think of one or more novels (or movies) that have shady characters. In the comments, list the title of the novel (movie) and the shady character. Now, by shady I mean to imply a character of doubtful reputation. A shady character is not definitely bad. Neither is she certainly good. Usually a shady character seems to be up to good but somehow gives the impression her motives are dubious. Sometimes they are. Sometimes they are not. Other characters are attracted to a shady character but never feel comfortable they should be drawn to her. Almost always, no matter how the shady character turns out in the end, the other characters are better off for having journeyed with the shady character for a time . . . but not always.

A shady character can be as subtle as Mr. Tumnus leading Lucy Pevensie into the woods. A shady character can be as enigmatic as Sunday taking Syme on a wild goose chase. A shady character can be as unpleasant as Haymitch Abernathy mentoring Katniss Everdeen; Katniss herself is a shady character. Shady characters are most of the people sitting around Edna Spalding at church in that final scene of Places in the Heart.

Got it? So now, name some shady characters and where you find them in literature or film. And do this, too. Tell me if you would like to journey through life with that person for a time.

This is what I am wrestling with of late. When I do this exercise and keep it safely contained to books and movies, I think to myself, “It most certainly is not going to be pleasant hanging around that shady character. But, how could I not?” I imagine the discomfort and also the growth of my soul. I feel more adventurous, more alive, more streetwise, more capable of empathizing with others and even my own fretful heart. This little exercise works out well in the end, so long as I stick to books and movies.

Not so when I invite real people from my real life into this imaginative experiment. There are some shady characters lurking around the margins of my life of late. They are the kind of shady characters who, if I met them in a novel, I would endure their company in anticipation of a worthwhile plot twist. But off the page, I keep my distance. So what is the difference? Should we extol the efficacy of shady characters, unless they are real? No need for risky plots in real life? How do you decide which shady characters make it into your life journey?

Dave is an author, educator, and advocate of living simply. Dave has spoken nationally and internationally about simplicity. He has appeared in Time Magazine, Mother Jones Magazine, the London Times, and The Guardian, and has been a guest of the 700 Club. His book The 100 Thing Challenge (HarperCollins, 2010) tells the story of his simple-living journey and the worldwide movement it contributed to. Dave holds an M.A. from Wheaton College and a B.A. from Moody Bible Institute. He works at Point Loma Nazarene University and lives in San Diego with his wife and three daughters.


  1. Joe Sutphin

    This is a great topic. And “shady” has a lot to do with the daily life and environment of the one calling the other shady. To Frodo, Strider was shady. To Bilbo, Gandalf was shady. To the folks of the Shire, Bilbo was the shady one. A lot of times people can tend to view unfamiliar and somewhat secretive as shady. Sometimes its that person who takes risks or is off on a whim frequently and has no roots who is viewed as shady.
    I have a friend who most around me view as shady, and he doesnt know the wiser. He has made some major life changes but his past is written all over his skin in ink and rough speech, but his heart is right. Yet, to the naive eye he is shady.
    In literature and film, I find it wonderful when shady meets shady and tries to become familiar while keeping shady. One of my favorite films of all time, the Twelve Chairs, by Mel Brooks, is filled with nothing but shady characters, all out for a single goal. It makes for a great story full of fun conflict and compromise.

  2. SarahR

    The photo of Aragorn represents the first shady character that I thought of. 🙂 Gollum is another shady one in the same story, in a completely different sense.
    Others that come to mind are:
    Long John Silver from Treasure Island (I’m still not sure whether he was good or bad!)
    Dustfinger from Inkheart (who did alot of selfish things, but carried the plot to a selfless end)
    Chiaroscuro from The Tale of Despereaux (all he ever wanted was Light).
    I think the key is following the Holy Spirit, in the end. Jesus hung out with some shady people, but not every shady person. He was completely in tune with the Father’s leading on the matter. Even people of selfish and corrupt intent can shape us and our path; on the flip side, even people who “look foul and feel fair” can turn out to be looking out for our best interests (or God’s) in the end. I think that discernment must belong to the Holy Spirit.
    Really interesting study! I can completely relate.

  3. Jamin Still

    David – the character I think of immediately is the Marquis de Carabas in Neil Gaiman’s Neverwhere. He’s a pretty great character who adds a lot to the story primarily because of his shadiness. He keeps you guessing.

    I don’t think I’d like to spend time with him, though, unless I was forced. It would be pretty risky and it seems it would be foolish to let this guy into my life. I might end up better for it, but I also might end up dead.

    This example aside, I like your question and what it’s getting at. It seems to me there has to be a balance between cautious prudence (I’m thinking of Proverbs and the advice to the young man in the first few chapters) and taking risks (I’m thinking of Jesus hanging out with the shadies). [I’m not entirely sure those are the two things in balance – cautious prudence and taking risks – but it’s what’s coming to mind right now.] I don’t often know what that balance should look like in my personal life, though. I suspect it’s different with every shady character.

    So I guess I think we’re supposed to recognize that the tension is there and grapple with it case by case, as opposed to either writing off every shady character in our lives or embracing every shady character in our lives.

  4. Brenda Branson

    Just finished watching “The Mystery of Edwin Drood” by Charles Dickens. The main character, John Drood, was a shady character cloaked in the prestige of a choir director. Definitely shady.

  5. Dan R.

    First one for me was Humphrey Bogart as Rick Blaine in Casablanca. Classic!

    And from the ‘shady is in the eye of the beholder’ angle (to borrow from Joe above), I’d propose that Jesus was very often the shady one to those who thought they had the light.

    Great post, definitely worth thinking about.

  6. aimee

    Here’s a good one-Severus Snape (from Harry Potter for those of you who haven’t read them yet).

    I can easily translate the thought of a shady character to real life friends and family, and it’s a good challenge.

  7. Mike whitaker

    Well my first thought was Aslan. Then my mind jumped right to Jesus. I don’t know if there was a more shady character in real life. Shady to those far and near. Just as shady today as he was a couple thousand years ago. Shady in where he went and goes, who he hung with and hangs with, what he did and does, what he said and still says, etc. He’s the ultimate shady character because he has the right and power to do us the most harm yet stoops to do us the most good. Both of which are very uncomfortable in the shadiest of ways.
    That wasn’t meant to be the Sunday school “right” answer, nor the trump card.
    Yes I long to be with him. What’s cool about this shady character is he brings us into shady places we would never have gone if weren’t following him.

  8. Will

    I don’t have a shady character to add, but I do have a thought to add:

    I wrestled with this exact thing for a while, but regarding the idea of “adventure”. I realized that I always yearned for adventure in my life—like what I would read about in books or see in movies and video games—but I felt like there was none in my life. So I started to think about what adventure is, and I ended up boiling it down to something like “when a person is put in a position where they have to do or endure a difficult thing without any certainty of how it will all turn out”. I quickly realized that if something that fit that definition ever actually happened to me, I most likely would NOT enjoy it, and in fact most of my life has been lived subconsciously avoiding exactly that sort of thing. So even though I felt a yearning for adventure, at the same time, I pushed myself away from it.

    After a lot of thought and prayer, I came to realize the key is that I don’t like uncertainty. I hate being in a situation where there is a chance that everything could end badly, but that element of risk is exactly one of the things that makes an adventure. The difference is that when you’re reading a book, you know that the adventure will turn out good, or even if it ends in tragedy, that there was a purpose to it all for you the reader (which, incidentally is why I think “realism” (read: nihilism) in stories totally negates the point of telling stories at all). In real life, though, we don’t know if the situation we’re in will end well, or if we’ll be left in a ditch somewhere or something, and that’s not enjoyable.

    However, as Christians, we DO know that everything will end good (at least on the grand scheme). We don’t know exactly how it will all work out, but we believe that God will win, Evil will be conquered, and we will end up living forever with God. So I discovered that the issue isn’t actually that life is uncertain, it’s that I often don’t trust God. When I do trust Him, though, my life becomes an adventure; suddenly I find myself able to do things and take risks I never would have done before, because—like when I’m reading a story—I know that it will all turn out OK in the end!

    And to bring that back around, I think interacting with shady characters plays off this same principle of adventure.

  9. Eowyn - Hannah Long

    Brenda already mentioned Dickens – he’s full of that type of character. (One can imagine the casting director for a Dickens film…”Yeah, shady character? Right, you’re hired.”)

    My favorite would have to be Sydney Carton in A Tale of Two Cities, but I also love Our Mutual Friend’s irresponsible Eugene Wrayburn and mysterious John Rokesmith (played by Paul McGann and Steven Mackintosh, respectively, to perfection in the 1998 miniseries.) However, (slight spoilers here) I think Rokesmith is more the shady character you describe than Eugene – for Wrayburn’s mystery is merely showy sarcasm and snobbery which lends him a cloak of unpredictable charm, but Rokesmith’s quietness hides deeper character. Perhaps part of the attraction with shady characters is the risk that it could be one, or the other – light or darkness. What is hidden? We human beings do love a good mystery. As Frodo observed, it’s a matter of sight – some people look fair, but are in fact foul, while others are hiding fairness beneath the foulness. And some are just foul, I suppose.

  10. Laura Peterson

    Dave, I love this post. (Nice “Places in the Heart” reference.) I’m pondering so many characters. Snape, for sure. Robin Hood, perhaps. Peter Pan. Jack Boughton in Marilyn Robinson’s “Home.” Definitely Glendon Hale in “So Brave, Young, and Handsome” and probably Davy in “Peace Like a River.” (Leif Enger seems to write shady characters pretty well.) Glen Hale is the example that I think fits best with what you’re describing–someone around the edges of your journey, decidedly shady but also offering a lot of life. I think Monte Becket does a pretty good job of navigating the questions that you’re asking. But…..I have no idea how to navigate them myself. 🙂

  11. Aaron

    Treebeard. Definitely shady. I mean, he actually provided shade. But also was a “shady” character. The Gunslinger in the Dark Tower series. Way shady. And awesome. Actually, just about all of the characters in that series.

    As for “real life”? My life has been enriched beyond measure by shady characters. I can think of two specifically. One ultimately followed a different path when friendship, love and grace became too frightening when, pardon the expression, “s— got real!”. But my friends and I can tell you some hilarious and, sometimes simultaneously, heartbreaking stories about him. He definitely put the “character” in “shady character”. He was alternately infuriating and ingratiating, manipulative and sincere, and I’m better for having known him and for risking on the side of love.

    The other shady character, who came from a similar background of brokenness in many ways, ultimately embraced the friendship, love and grace offered to him when our relationship came to the point of facing some difficult stuff. He struggled, but God wrote an incredible story with his life and ours. He passed away a year ago, and I can’t tell you how much I was blessed by his presence in my life.

  12. Sally

    The first person that came to mind was Count Fosco in Wilkie Collins’ “The Woman in White.” I still get knots in my stomach thinking about him, yet the story would be, at best, hollow without him.

    On the other hand, Sydney Carton (A Tale of Two Cities) is exactly the type of shady character that I wish I knew.

  13. Holly Deutsch

    After seeing the picture of Strider, Aberforth Dumbledore came to mind. Also, certainly Snape – They both make you ask that question “Is he trustworthy?”

    Hannah, I very much agree with you about Rokesmith (Our Mutual Friend). He’s one of my favorite shady characters. There’s so much mystery surrounding him, then there’s his inner conflict of “will he reveal his true self?”

    Since shady characters are those that their trustworthiness is unknown and/or they have a rather mysterious past, I would be wary of immediately becoming friends with a shady character, yet they are the people that keep life interesting. They bring new adventures & plot twists into the stories of our lives.

  14. Matthew Benefiel

    -Walter (a.k.a. “the filthy beast”) from the movie Father Goose.
    -Mark Studdock from “That Hidesous Strength” – Only because you can really depend on his choices, even though the book it mostly from his perspective.
    – Strawberry and Bigwig from “Watership Down”
    – Achelles from “Ender’s Shadow” – Though technically you are warned about him
    – Strider and Snape mentioned above are prominent

    I suppose the lists could go on and my memory is not serving me well right now. What I seems to notice though is all the shady characters are no longer shady at the end of the book, unless the book remains a mystery like Long John Silver, but even him you see that while he is vile and a killer, he can be swayed by some love. So in the end the “shady” part is the fact that you don’t know the person. Achelles from Ender’s Shadow is but a brief episode of shady really because the Bean tells the reader not to trust him and since you relate so well to Bean you trust his judgement.
    In real life it is much the same way, the less you know about someone the more mysterious they are. Sometimes we don’t give enough mystery to people, thinking we know who they are, until you find out more about them. So as another poster said, it is a balance between prudence and I might say love of people. To want to find out someone’s story. To some degeree this can be done with prudence, but usually we are too self centered (scared, lazy, lacking in confidence and therefore courage, etc…) to take the time or overcome our faults to get past the “shady.” In books it is easy, because you have no choice, but you have no commitment beyond emotional. Sometimes we are shady ourselves because he hold back instead of showing people who we really are, or perhaps we don’t wish to be judged by who we are.

  15. Matthew Benefiel

    Sorry, you can’t depend on what Mark Studdock’s choices.

    Thinking some more I can’t help but compare characters like Ender vs Katniss. With Ender you are in his head, so you know his thoughts and his ideals. So while he take extreme measures you know the reasons why and how much it hurts him, so you don’t think of him as shady, but you could if he was written differently.

    Now even after finishing Hunger Games you still could consider Katniss shady, because the first person never really lets you know her true motives for doing something, so while you see her make decisions, you don’t always know the true motive.

    To apply that to real life, without really knowing someone we tend to invent the motive behind their thinking. I know I’m guilty of that with even my wife. Without communication, I don’t always know why she does something and therefore I begin to judge her based on my misconceptions. I think the same could be said for Strider and Snape, both who had reasons to hide their motives, but when they are found out you idea of them completely changes and you give them a trust you didn’t before (or lack of trust for characters that don’t deserve it like Gollum).

  16. Laure Hittle

    i’m reading The Sparrow right now, and the character that i think of right away for this question is Emilio Sandoz. The book is written in two parallel storylines, though, so while the story set after the events have occurred shows him as a very shady character (he even admits that the charges against him are true, and seems pretty evasive at times), there’s a sense based on the earlier story that his shadiness is covering up not pure evil, but some tragic mixture of good intentions and difficult circumstances and, well, i don’t know what yet.

    When i think of other shady types, Emilio is joined by the likes of Snape and Artham (and Podo and Kalmar) and Sydney Carton and Judas Iscariot, and that immediately brings to mind the archetype of tragic figures. Tragic figures are shady in part because they are unable to be honest with those around them out of fear of being known, and, to varying degrees, are unable to be honest even with themselves. They can’t trust their own shadiness.

    i love tragic figures. i want to mother them. And it’s more dangerous to do that in real life than in stories, where you can close the book at the end and be insulated from that character’s influence to whatever degree you choose. But if shady characters are tragic, then they are in need of unconditional love and grace—dangerous to give, dangerous to receive, but redemptive and beautiful and necessary. And we need this too.

    That doesn’t tell you or anyone what to do in specific circumstances regarding specific people—and the inclusion of Judas Iscariot in my list above proves that there are no guarantees that loving shady characters will end well. It hasn’t always worked out well for G-d, either, and He once told Jeremiah to stop praying for the people of Judah, so clearly there’s no straightforward answer. But maybe it helps to think about how our ministry of reconciliation beautifies the choice to love messy humans made in G-d’s image.

  17. Tom Murphy

    David, aren’t we all shady?

    Maybe a part of the Good News is that we are all shady – for those that acknowledge their “shadiness” are some of the most helpful folks I have met in life…

    BTW, if someone doesn’t own up to their “shadiness”, I tend to stay clear. They usually have an agenda. And the agenda is normally always self centered…

  18. Zach

    What a great post and question! I’d echo the above mention of the Marquis from Neverwhere. I’d also name two characters from Carlos Ruiz Zafon’s masterpece The Shadow of the Wind. Both Lain Coubert/Julian Carax and Barcelo come across as shady but Zafon leaves you convinced that they are noble, which in the end, they are.

  19. Sofia

    Mr. Rochester from Jane Eyre comes to mind as another exemplar. In that situation, a separation became necessary before he & Jane could be reunited in a mutually beneficial way…

  20. Esther O'Reilly

    I would say it’s impossible for us to counsel you without further details on the nature of your real life characters’ shadiness. For example, one woman I know of spoke to a group of women about her experience with a mixed group of men and woman who asked if she could take them into her home. They left in the night, and years later one returned with what they had stolen from her and said he was the only one who had kept the other men from murdering her in her sleep. But perhaps you just mean shady as in “harmless, but odd and eccentric.”

  21. Dave Bruno

    Thanks so much for the great comments!

    Yes, Tom, I think we’re all a bit (or a lot) shady. I was talking with some folks offline about this question and one person identified untrustworthy shady characters as those who are not self-aware. I thought that was a good angle. When a shady character has self-awareness of his faults and acknowledges the ambiguity of navigating life well, that’s a good indication he’ll turn out well in the end. But shady characters who consistently show a lack of self-awareness probably are headed to a bad end, and likely are willing to take as many people as possible with them.

  22. S. J. R.

    First characters I though of were Snape, Aragorn, and Artham, and then Natasha Romanov from the Marvel Cinematic Universe. She is the very definition of ‘shady character’ though she doesn’t always look it. You never know what her motives are, but you can hazard a guess that their not always good.

    I love these characters in stories, and always want to help them, but it’s different in real life, because you don’t know real people as well as you know characters. You don’t know they won’t hurt you. You don’t know if they really want or need your help. Or rather, they may need your help, but not know it.

  23. R.J. Anderson

    I also thought of Natasha Romanoff / Black Widow first thing, and an interesting side-note to her shadiness is the character arc she goes through in Winter Soldier. In almost any other movie she would be the worldly wise femme fatale who gets (or even seduces) the straitlaced, idealistic Steve Rogers into a greyer view of morality. But in this movie, he remains the moral centre, it’s his ideals of goodness and freedom and trust that are validated and upheld, and she’s the one who ends up giving up a lifetime of shadiness and false pretence and stepping into the light. (And best of all, it happens as a result of their enduring friendship and mutual respect, not a romance. SO REFRESHING.)

    Another amazing, compelling, and frequently baffling shady character is Gen, from Megan Whalen Turner’s Queen’s Thief series. Which I highly recommend to Christian fantasy readers, for all the reasons I laid out in this essay on why I love Turner’s books.

  24. Jamie Cain

    Thanks for the provocative question. I thought first of Frederick Buechner’s Leo Bebb, that “Happy Hooligan,” and then almost immediately of his foil, Antonio Parr. Both are shady, I think.

    To your second question, I’d have to answer as Gildor does and say, “yes and no.” And it quickly gets real up in here, because I sometimes think my father was Bebb incarnate. That difficult journey has borne some some good fruit–and may still.

    I thought, too, of an ESPN: The Magazine cover story about DeSean Jackson, and his description of marginal characters in his life as “certain people” who do “certain things.” The vagueness was calculated to protect his career, but he made it plain that those people cared for him, and he for them, and he would not kick them to the curb out of convenience or self preservation. Sobering.

  25. Carey Pace

    What a fabulous, thought provoking question. How have I missed considering the shady characters, and their impact both good and bad, in my real life?

  26. Nathan

    Sherlock Holmes
    Jean Valjean – Les Miserables
    Abbe Busoni – Count of Monte Cristo
    Tom Bombadil – LOTR
    Andy DuFresne (or really, Red too) – Shawshank Redemption
    The Uncles – Secondhand Lions
    Doc Holliday – Tombstone
    Robin Hood (Stephen Lawhead’s iteration)
    Dread Pirate Roberts! – Princess Bride

    And one of my favorites…

    My dear Glendon Hale – So Brave, Young, and Handsome

  27. Laure Hittle

    Laura P.—i would love to talk about The Sparrow with you. i’m probably about 3/4 through right now (they’ve just met Supaari), and i know i will have lot to wrestle with by the time i’ve reached the end. How shall we facilitate that? Post here? Email exchange?

  28. Laure Hittle

    (You know, Supaari is a way shadier character than Emilio. Emilio is threatening puzzle to those trying to make sense of what happened on Rakhat even as the reader senses that he is a victim, but Supaari is, from the very beginning, a mix of sinister and tragic, bootstrappingly noble but monstrously dangerous.)

  29. Glenn

    Been re-watching Alias lately, and this discussion came to mind – so many shady characters in that show – Jack Bristow most of all, Arvin Sloane, Irina Derevko. The last two are villains, but imbued with sympathy and humanity.

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