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Jane Canary, based on the legendary Calamity Jane, is one of the more complex and fascinating characters in the city of Deadwood. Incredibly tough and brazen on the outside, she has been shown to be deeply wounded and emotionally delicate when prodded. Clothed in garments normally only donned by males, she is indeed sometimes mistaken for a man in the early on in the show. Her appearance is that of someone well acquainted with life in the outdoors. Her face is perpetually dirty, and she speaks with a mush-mouth slur, exacerbated by heavy drinking.

Jane appears in the series as a companion of Wild Bill Hickok, the great gunslinger known to all in camp well before his arrival. Along with the stalwart Charlie Utter, the three arrive in Deadwood uncertain of their purpose, as Bill is at a point in his eventful life where he no longer cares for anything other than playing cards. Jane has a deep respect for Bill and no doubt looks to him as a father figure. She is often rather spiteful of Charlie as he seems to her to be a rival for Bill's attention. They are not long in camp before Wild Bill is killed, as in real life, by fellow gambler Jack McCall. The result of this death is devastating to Jane, and only causes her to become all the more insecure and fearful, emotions which she attempts to numb through excessive whiskey consumption. Jane is often so hilariously drunk that she is discovered by Charlie lying in the street, and once just leaning up against a wall balanced on her forehead.

Jane's primary form of communication is shouting obscenities, and is one of the better cursers in the camp, which in Deadwood is quite the feat. Of course, this behavior is no doubt related to a deep hurt and terrible fear instilled in her at an early age, as is evidenced by her desire to protect Sofia, and the other children in camp from harm. When confronted by Al Swearengen, Jane is reduced to abject terror, as if reliving an experience of terrible violence in her past. She is very mistrusting of most males and has another brief and terrifying encounter with Cy Tolliver later in the series. (Interestingly, both men make their living off of the subjugation of women). The Character of Jane Canary stands as a good example of the hardships women endured in the 19th century and indeed, throughout all of human history (though she is spared some due to her external appearance and brash nature).

Despite the obvious fragility of Jane's inner world, she possesses also an inner strength in her compassion for the sick and dying. Assisting Doc Cochran on more than one occasion in the difficult task of healing the camp's ailing denizens from various ailments, from gunshot wounds to an outbreak of smallpox. Even the Doctor himself tells her she has a gift for nursing. During her self-imposed exile from camp after Bill's death, she happens upon Andy Cramed, who unwittingly brought the smallpox virus with him to camp and was ordered to be left to die in the woods by Cy Tolliver, restoring his health from near death using only water and whiskey and her deep inner reserve of compassion.

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