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Annie Oakley, “Little Sure Shot”

Annie Oakley, "Little Sure Shot"
  • Alias: Little Sure Shot
  • Gender: Female
  • Race: Human
  • Occupation: Sharpshooter, Performer
  • Religion: Unknown
  • Allies: Buffalo Bill Cody, Sitting Bull, Wild West Show troupe
  • Enemies: N/A (No known specific enemies)
  • Abode/Base of Operations: Traveling performer, no fixed abode
  • Nationality: American
  • Languages: English
  • Alignment: Chaotic Good
  • Affiliation(s): Buffalo Bill’s Wild West Show
  • Significant Others: Frank E. Butler (Husband)

Annie Oakley, the Sharpshooting Sensation, captivates audiences with her exceptional marksmanship and captivating performances. A petite and graceful woman with a fiery spirit, she defies societal expectations and proves that skill knows no boundaries. Born into a humble family, Annie’s natural talent with a rifle emerged at a young age, earning her a reputation as a prodigy. Driven by a desire to provide for her family and escape poverty, Annie embarks on a journey to showcase her unparalleled shooting abilities.

With each carefully aimed shot, Annie not only entertains but challenges gender norms, demonstrating that women are just as capable as their male counterparts. She travels the country, participating in shooting competitions, dazzling audiences with her precision and earning numerous accolades. Annie’s ultimate goal is to empower women and inspire them to pursue their dreams fearlessly.

Her petite frame belies her incredible skill; with piercing blue eyes and golden locks cascading down her shoulders, Annie radiates determination and confidence. Clad in her signature fringed buckskin outfit, she commands attention as she flawlessly handles her trusted rifle.

Driven by her passion for shooting and a desire to prove herself, Annie Oakley continues to leave an indelible mark on the Wild West, challenging conventions and inspiring generations to come.

Annie Oakley

Annie Oakley, "Little Sure Shot"

Medium humanoid (human), chaotic good

Armor Class: 15 (fringed buckskin outfit) Hit Points: 82 (15d8 + 15) Speed: 30 ft.

10 (+0)18 (+4)12 (+1)14 (+2)16 (+3)20 (+5)

Saving Throws: Dex +8, Wis +6 Skills: Acrobatics +8, Perception +6, Sleight of Hand +8 Senses: passive Perception 16 Languages: English Challenge Rating: 7 (2,900 XP)


  • Sure Shot: Ranged Weapon Attack: +8 to hit, range 80/320 ft., one target. Hit: 13 (2d8 + 4) piercing damage.
  • Trick Shot: Annie performs a dazzling trick shot, attempting to disarm or disable her target. She makes a ranged attack against a creature, and if she hits, the target must succeed on a DC 15 Dexterity saving throw or be disarmed or have their movement speed halved until the end of their next turn.

Legendary Actions

Annie Oakley can take 3 legendary actions, choosing from the options below. Only one legendary action can be used at a time and only at the end of another creature’s turn. Annie Oakley regains spent legendary actions at the start of her turn.

  • Quick Draw: Annie reloads her weapon with lightning speed, allowing her to make an additional ranged attack.
  • Precise Aim: Annie takes a moment to carefully aim, granting her advantage on her next ranged attack.
  • Inspiring Presence: Annie uses her charismatic presence to inspire her allies. One ally within 30 feet gains advantage on their next attack roll or saving throw.


  • Carbine Rifle: A finely crafted rifle that has been customized to fit Annie’s exceptional skills.
  • Revolvers: A pair of ornate revolvers, always kept within easy reach.
  • Fringed Buckskin Outfit: A stylish and practical outfit made of supple buckskin, adorned with intricate fringes.
  • Trick Shot Kit: A collection of various tools and accessories that aid Annie in her trick shots.
  • Ammunition: A plentiful supply of ammunition to keep her firearms loaded.

Additional Features

  • Sure Shot Mastery: Annie Oakley has advantage on all Dexterity (Acrobatics) checks related to her shooting abilities.
  • Trick Shot Expert: Annie Oakley can attempt to disarm or disable a target as a bonus action.
  • Quick Reflexes: Annie Oakley has advantage on initiative rolls.

Note: The Challenge Rating and specific abilities can be adjusted based on the desired power level and campaign setting.

Currently in the World

Annie Oakley is a petite woman with a fiery spirit and sharp eyes. She stands at around 5 feet tall, with a slim yet athletic build. Her blonde hair is neatly braided, and her piercing blue eyes reflect her determination and passion.

Currently, Annie is standing on a dusty stage, the spotlight illuminating her as she holds a gleaming rifle in her hands. She wears a fringed and embroidered leather outfit that hugs her figure, allowing for ease of movement during her impressive shooting displays. The crowd watches in awe as she effortlessly hits targets with pinpoint accuracy, her movements precise and fluid.

Surrounded by the sounds of cheering spectators and the smell of gunpowder, Annie’s current surroundings are a bustling Wild West show arena. The air is filled with excitement and anticipation, as people from all walks of life gather to witness her remarkable marksmanship skills.

Annie’s mood is one of confidence and focus. With each shot, she showcases her exceptional talent and proves her place as one of the greatest markswomen of her time. She takes pride in her abilities, always pushing herself to surpass expectations and inspire others to believe in their own potential.

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