A Little Help From My Friends: The Lovable Rogue

Good morning, threes of fans!

We are now well and truly into the thick of HalloGivChristNewEve season, and I am feeling it. Not in a Buddy the Elf kind of way, but more in an “oh my gosh, it’s upon us, and I have not started anything” kind of way. I would love for Buddy the Elf to show up and help, but also, that would be incredibly stressful, so maybe I’ll just Grinch my way through it all. That may sound negative, but think about it–he starts out all grumpy, but he ends up with a heart three sizes bigger.


Let’s hope for the best.

I’m finally getting back to my posts about side characters, and I decided to take a closer look at each of the four tropes I outlined a couple of weeks ago. I want to look at the purpose of each, the characteristics each one should have, and some of the dangers inherent in creating each one. That sounds like a lot for each post. I’ll try to keep it short, but… well, you know…

This week: The Lovable Rogue as a side character.

The Rogue as Foil

Who doesn’t love a rogue? Some of the best characters in all of storytelling history have been Lovable Rogues. Of course, as an unrepentant GenXer, my thoughts immediately go to Han Solo. I feel a little bit like Han Solo defined the antihero rogue for the modern era. Would we have had Jack Sparrow, Tony Stark, or Danny Ocean (the George Clooney version) and his crew without Han Solo? Maybe, but maybe not exactly.


The thing about Jack Sparrow, Tony Stark, and Danny Ocean is that they are main characters. One could argue that Jack Sparrow is never really redeemed (a topic for another day, because I think there are two sides to that one), but Tony Stark and Danny Ocean both have redemptive arcs (sort of).

The best rogues, I think, are the side rogues–the friends of the main character, the ones who can get away with all the things the main character can’t. One of my favorites from literature is Silk from The Belgariad and The Malloreon. Silk never rises to the level of main character, nor does he have a true redemptive arc (in part because he’s honestly not that bad to begin with). Instead, Silk remains a happy and valuable side character. Even when Belgarath slips into his roguish persona, he’s always basically bound to certain rules and a higher nature. And when Silk finally settles down with Velvet, he marries the female version of himself.

I confess that I had Silk in mind when I started writing Brody Reid. Brody has his fingers in a lot of things all over Taura. He knows where the bodies are buried, figuratively and literally, I suspect. He’s talked or gambled himself out of countless scrapes, and he has enough secrets tucked away in his head that he’s as protected as he is under threat. The great thing about having dirt on everyone is that everyone both wants you dead and feels obligated to protect you.

The Lovable Rogue can get away with things others can’t. The staid and solid character might be bound by position or visibility to operate within the bounds of convention and law, but the rogue–well, all bets are off. The rogue can do or say anything. The main character may scold, cajole, or bribe the rogue to behave, but it will never work. Besides, the main character usually needs the rogue since the rogue’s sins usually help achieve the main character’s goals.


Creating a Rogue

The rogue characters sort of create themselves. They seem to leap fully formed from the head of the author. It was certainly that way with Brody (and, to be candid, with Connor at first). There are certain characters you can just put on a page and let them go, and they kind of write themselves.

At some point, though, they have to have a little structure. They don’t have to be quite as fully formed and fleshed out as a main character, but they need some boundaries, or they’ll cross all the lines and take over the story.



The best rogues have at least some of the following characteristics:

    • Money: This might seem shallow, but it’s easier to write a rogue who has at least a little money. It doesn’t matter much how he got it–he could be a thief, a rich son, a merchant, whatever. He can definitely pursue more money, or he can be always sort of walking the line between wealth and destitution, but having something to fund his endeavors is really helpful. A great example of this is any rich Gentleman Thief–think Thomas Crown. He doesn’t need to steal the art. He does it because it’s fun.
    • An object of loyalty: Since rogues don’t have much in the way of strong principles or conscience when it comes to following rules, it helps to give them someone or something to be loyal to. This object of loyalty kind of invokes the idea of honor among thieves–the rogue might not particularly like all of the official rules, but he will do anything for one particular person. Jack Sparrow’s loyalty lies with the Black Pearl. Danny Ocean’s loyalty lies with Tess.
    • A line: It really helps for a rogue to have a line he won’t cross–and to show that line clearly. The rogue might be a thief, a liar, a gambler, a cheat, even a little bit violent, but he has lines he simply won’t cross. It’s good when these lines are commonly agreed on across cultures. If your rogue won’t hurt children or kick stray dogs, we know he has some limits, and it’s easier to like him. And I think that the rougher the world is, the clearer that line has to be. If everyone in the world you’re writing is deceptive and cruel, you need to clarify early and often that your rogue has clear lines he won’t cross–no matter the price or cost.
    • A sharp wit: Obviously, this is everyone’s favorite thing about a rogue. He doesn’t necessarily have to be the smartest guy in the room, but he does need to be quick-witted and willing to say audacious things.
    • A special skill or talent: Silk had his secret Drasnian language. Han Solo was a heckuva good pilot. The entire Ocean’s crew is made up of people with one particular skill and a talent for keeping quiet. Let’s be honest–it would be tough to tolerate a rogue for long if he didn’t have a special talent or skill. One caveat: if the rogue is a main character, I don’t think this is as important.



The Big Danger of the Rogue

The thing about a roguish character is that he can easily become too big to contain and steal the spotlight from the main character. Some rogues end up stealing the spotlight and becoming main characters in their own right. Han Solo is the perfect example of this phenomenon. I confess that I don’t know everything about the development of Han Solo as a character, but the fact that he stayed around to eventually have his own movie and show up in the Star Wars sequels makes it pretty clear that the character was too big and too well-loved to stay confined to one movie.



I confess–it’s tough to contain a rogue. When I first started writing Ravenmarked, I really didn’t intend for Connor Mac Niall to be the main character. The whole book and series was supposed to be Mairead‘s story. Connor and Mairead were always intended for each other, but I never thought that he would be the central figure. I think he became the main protagonist in part because of his huge personality. He just sort of walks on stage and takes over.

To cast a rogue in a side character role requires that you rein him in and keep him under some degree of control, I think. There are a few ways to do this:

  • Control screen time: The easiest way to keep your rogue under control is to limit how much time he’s on the page. Send him on side quests–rogues love a side quest. Bring him back for comic relief when you need to lighten the mood. Or confine his use to his one special skill and let him spew all of his audacious comments during those scenes.
  • Hide the backstory: We tend to sympathize with characters we know the most about. If you keep your rogue’s backstory mostly hidden, your audience will be less likely to develop strong sympathy for him, and it will be harder for him to steal the plot. (It’s okay to slip in a few stories about previous audacity, though; we love those stories.)
  • Make your main character as big as possible: At this point in my books, there is no way that Brody Reid could overtake Connor Mac Niall as main character. Connor is just too big and too central. When the main character has a big personality, it’s almost impossible for a rogue to overshadow him.
  • Introduce the Lovable Rogue late: I think introducing Brody late into the story helps keep him in his proper place. We’ve had three books to get to know Connor, and Brody only had a little bit of screen time in one of them. He just won’t have enough time to be anything more than a foil and an extra sword in the coming war.



All that said… the truth about a great Lovable Rogue is that they have minds of their own. It’s really tough to keep them confined, and they are often at their best when they stretch the limits of… well, everything. And honestly, the world is a better place for having Han Solo, Danny Ocean, Jack Sparrow, and all of the other Lovable Rogues who got a little out of control. Take all of this with a heaping boulder of salt, and let your Lovable Rogue be himself.

For these last few weeks of 2023, I’m going to hover between finishing out my ten rules series and talking about side characters. Those two themes will take us into 2024, and then… who knows? I’m hoping to have some updates on projects soon.

In the meantime, stay warm out there!



* Footnote: I realized I mostly wrote this under the assumption that Lovable Rogues are all men, mainly because I had Brody Reid in mind as I was writing. But I confess: I think the best Lovable Rogues are men, largely because men can get away with things women can’t and men and women have different motivations, both in real life and on the page/screen. Women as Lovable Rogues just play differently, in my opinion. This is, obviously, a topic for another time, and your mileage may vary.



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