I wanted to share another subclass concept I’ve been working on that encourages pulp action and swashbuckling gameplay. The following subclass let’s you play a PC who uses their smile, quick wits, and the odd dirty trick to find their way in and out of trouble. This archetype is pretty flexible and would allow you to play a fast-talking lovable rogue such as Jack Sparrow (Pirates of the Caribbean), Han Solo (Star Wars), Mal Reynolds (Firefly), and Rick O’Connell (The Mummy), Sophie Devereaux (Leverage), Faye Valentine (Cowboy Bebop), or even Catwoman (Batman). Thematically these rogues are great at finding their way into trouble and deep down have a good heart.

Please let us know in the comments below what you think of inviting this scoundrel to your table (as a GM or player). Even better… tell us what you would recommend to make improve this subclass. Thanks!

Scoundrel – Rogue Archetype

As a Scoundrel, life has not been easy, but you have figured out how to turn the tables a bit in your favor. You use your smile, quick wits, and odd dirty trick to find your way into and out of trouble. Making friends is easy and even your enemies have trouble resisting your charm. When things go sideways and the time for talk is over, you are fine with fighting your way out of a bad situation too. Some call you a pirate, smuggler, outlaw, or brigand, but you are just doing what you need to stay on the winning side.

Scoundrel Features

Rogue LevelFeature
3rdBonus Proficiencies, Fast Talk, Unsavory Connections
9thDirty Trick
13thSmooth Talk
17thTight Spot

Bonus Proficiencies

When you choose this archetype at 3rd level, you gain proficiency with one type of gaming set and improvised weapons. In addition, you can sneak attack with an improvised weapon that you wield in one hand.

Fast Talk

Starting at 3rd level, your have become adept at using your words to cause confusion, anger, or just to catch someone off-guard. You gain an additional way to use your Sneak Attack: you can use the bonus action granted by your Cunning Action to Fast Talk a creature who can hear and understand you that is within 30 feet. The target must make a Wisdom saving throw with a DC of 8 + your proficiency bonus + your Charisma modifier. On a failure, you don’t need advantage on the attack roll to you use your Sneak Attack against the target if you are within 30 feet of it and you don’t have disadvantage on the attack roll. All the other rules for Sneak Attack still apply to you.

Unsavory Connections

When you choose this archetype at 3rd level, you can draw on your connections to locate people and things that are hard to find. You have made some important friends, and your connections go beyond the mere contacts of a common criminal. By spending four hours carousing within a populated area you can gain one of the following (at your GMs discretion):

  • Knowledge of the profession, a recent location, and the affiliates of a humanoid creature who currently resides there.
  • Access to any rare or illegal goods and services that are available.
  • Offer of employment from a criminal enterprise.
  • Access to a hidden pathway or entrance that is known to your connections.

Dirty Trick

Starting at 9th level, you learn to use your surroundings to turn a retreat into an opportunity. When you take the Disengage action, you can find an object (such as debris, a torch, or a drink) to toss at a creature within 5 feet of you. The target must make a Dexterity saving throw with a DC of 8 + your proficiency bonus + your Charisma modifier. On a failure, the creature suffers disadvantage on the next attack roll it makes before the start of your next turn.

Smooth Talk

At 13th level, you have mastered saying what people want to hear and turning foes into friends. When making a Charisma (Deception or Persuasion) check, you can use Smooth Talk and gain advantage on the roll when interacting with a creature, even if they are hostile toward you.

In addition, if you use your Fast Talk feature and the creature fails their saving throw, you can add your Charisma modifier to your next attack roll.

Tight Spot

Starting at 17th level, you have become an expert at combining words and weapons to get out of tight spots. When a creature misses you with an attack, you can use your reaction to make an attack against that creature, adding your Charisma modifier to the roll. In addition, you can move up to half of your movement without provoking opportunity attacks.

Once you use this feature, you can’t do so again until you finish a short or long rest.

Art Credit: Mariam Trejo