How to Roleplay a Rogue (Samples and Help with the Dialogue)

The core of an outlaw is a harsh sense of justice. The most engaging outlaws are those who understand that there is always something above the rules. Link this with one of the main principles of writing a character: Every character should have a purpose and goals, even one goal in each interaction, at least. From mundane to extraordinary goals, it doesn't matter. Here, your character may be trying to profit with the conversation or determine whether you are just a snitch working with law enforcement.

The goal during the conversation may also determine whether your character is angry, interested, or upset, for instance, compare the tone of Calvin Candie in Django after he is offered twelve thousand dollars for selling his slave:

                         CALVIN CANDIE
          Well then we got nothing more to talk
          about. You wanna buy a beat ass nigger
          from me, those are the beat ass niggers
          I wanna sell.

                         DJANGO
          He don't wanna buy the niggers you wanna
          sell. He wants the nigger you don't
          wanna sell.

                         CALVIN CANDIE
          I don't sell the niggers I don't wanna
          sell.

Dr.Schultz chimes in thoughtfully;

                         Dr.SCHULTZ
          You won't sell your best. You won't even
          sell your second best. But your third
          best... .you don't want to sell him... but if
          I made you an offer so ridiculous you'd be
          forced to consider it... . who knows what
          could happen?

                         CALVIN CANDIE
          What do you consider ridiculous?

                         Dr.SCHULTZ.
          For a truly talented specimen,
          ."The Right Nigger"...?
          How much would you say, Django?

                         DJANGO
          Twelve thousand dollars.

Calvin Candle takes in the figure.

                         CALVIN CANDIE
          Gentlemen, you had my curiosity. Now
          you got my attention.

A few scenes after, the dialogues of Calvin Candie change to:

                          CALVIN CANDIE

          Oh hardly a ride at all. We'll still be in

          Chickasaw County. Five hours... tops.

          There you can get a look at my best

          specimens. Have dinner with my sister

          and I. Spend the night at Candyland as

          my guest.

When Calvin smells the twelve thousand dollars, he becomes cooperative and kind with both Schultz and Django. The following dialogues are hilarious, but those never betray is the initial goal of making money. Calvin is a businessman above his bigotry against African American slaves. 

 

What works for me is to have clear the goals of my character. It's always fun to listen these characters brainstorming loudmouth about the pros and cons of certain path of action. This works very well when someone is requesting something from the character, including information or help. 

There is some cynicism rooted in their behavior because of such a perspective. When you are writing your dialogues, keep in mind that the right point is a lot of sarcasm and inappropriate chat because they are often capable to see through the bullshit that people conceal as courtesy, manners, or kindness. These characters believe that if someone is being nice, they most likely want something from them.

Most of the stereotypes with these characters are womanizer morons, rotten bureaucrats, reckless warlocks, charming smugglers, bounty hunters, criminal businessmen, etc. Don't feel restrained to these stereotypes. You can actually combine or leave these categories because what is behind is this idea that conventions and customs are made to be broken. This idea drives the dialogues and often make their language unpolite and funny.  

Let's go now for some ideas to work on in different situations. The best way to learn is actually reading dialogues from these kinds of characters. 

Descriptions to enter the scene.

• Rick saunters into the scene, leans against the bar next to Yvonne. But he pays no attention to her. She looks at him bitterly, without saying a word. (Rick in Casablanca).
  

• After a moment, the door to the townhouse opens and a MAN emerges, curious to see what the commotion is outside. As the MAN comes into the light we see he's dressed in a crisp tuxedo with collar unfastened, no tie (...) he has intelligent eyes, michievous lips, and a deep baritone dripping with Southern charm (Francis in House of Cards)

• He drops his hat and overcoat on the bed and exits into the kitchen, returns after a moment with a tall bottle of Bacardi. He pours a drink, drinks it standing, pours another (Spade in The Maltese Falcon)

• The man facing him is lean, hollow-cheeked, and dressed in grey. Detached and efficient, he looks like a cop or an accountant. His name is Holden and he's all business, except for the sweat on his face. (Holden in Blade Runner)
  

Greetings

• "Do you know me? I guess no."
  

• "Who's that stumbling around in the dark? State your business, or prepare to get winged! (Dicky Speck in Django.
  

Some funny responses 

• "I don't know the polite word for it."

• "I know you despise me. We always hate in others that which we most fear in ourselves. And you and I are very much alike." (Belloq in Riders of the Lost Ark)
  

• "Now you're getting nasty." (Indy in Riders of the Lost Ark

• "Fair enough... but I'd feel better about it if you'd have a drink with me" (Spade in The Maltese Falcon)

• "Not for sure. But I'll venture a guess."

• "Calm yourself gentlemen, I mean no harm. I'm simply a fellow weary traveler." (Dr. Schultz in Django)
  

Flirting

• "I was informed you were the most beautiful woman ever to visit Casablanca. That was a gross understatement." (Renault in Casablanca)
  

• "You're a very difficult woman to read"

Some mocking 

• "You ain't very talkative, ain't you?
  

• "I'm just chewin' the dog, mister. It's how I am. I don't mean nothin' by it."

Questioning

• "You have something on your mind. Why don't you spill it? (Rick in Casablanca)
  

• "I'll put my cards on the table, I think you know where those letters are." (Ferrari in Casablanca)

• "A very puzzling fellow, this Rick. What sort is he? (Casablanca)

Threats 

• "Consider the fact that I ain't put a bullet in your embrace, old man. You were supposed to look after the place (...) Hold your excuses until you [ain't] figured out which one to use." (Marston in Red Dead Redemption)

• "I suppose you know what you are doing, but I wonder if you realize what this means?" (Renault in Casablanca)

Apologize

• "I can only say I’m sorry so many times."(Indy in Raiders of the Lost Ark)
  

• "It just doesn't pay to be the nice guy."
  

I give a fuck phrases 

• "I stick my neck out for nobody. [A wise foreign policy.]" (Rick in Casablanca)

• "I don't care about him because I take no stock in dead people."

• "Turn the dump upside-down if you want. I won't squawk (pause) if you've got a search warrant."(Spade in The Maltese Falcon)

Random Action

• Francis kneels down beside the dog. It's an awful shape. He tenderly strokes the dog's head. "Shh. It's okay." With cool-headed deliberateness, Francis calmly places a hand around the dog's neck and begins to put it out of its misery. The dog's muffled whimpers cease. Francis looks down. (Francis in House of Cards)

• He bows her out, shuts the door, returns to his desk. He takes tobacco and cigarette papers from this vest pocket but does not roll a cigarette. He sits holding the papers in one hand, tobacco in the other, and looks with brooding eyes at his dead partner's desk. (Spade in The Maltese Falcon)

• Ace raises his riffle towards the German [and] cocks back the riffle hammer. The doctor, throws his lantern to the ground, enveloping him in darkness. (Dr. Schultz in Django)
  
• He takes Django by the arm and leads him into the entryway of the establishment. The nervous black slave and the confident German dentist walk into the saloon.