I need an analysis of this painting. In approximately what time-period was this work created (years are acceptable) What is the subject matter (What kind of activity is being depicted?) Can you tell if the artist takes a position towards his subject (favorable/unfavorable), or does he remain neutral/unbiased? Why do YOU think this painting is important? (What can we learn from it? What was Catlin trying to show us, the viewers, 180 years later?)

Having never seen this painting before, I will first offer my own initial impressions, and then we’ll look up the artist and the history. Your own prior knowledge and experience can tell you a lot about the meaning of any artistic work, even if you don’t know anything about it.
I see two Native Americans, one in traditional dress, and the other in vintage European garb. I’m guessing this scene is set during the American western expansion, which I know took place in the 1800s. Some of the Natives held on to their ancient traditions, while others adapted (or were forced to adapt) to the new ideas that the European immigrants brought with them.
The character on the left is wearing a traditional feathered headdress and holds a peace pipe (both highly spiritual symbols), while the one on the right wears a top hat with one bright feather and smokes a cigarette. He seems, to me, to be more interested in the meaningless shallow finery of the Europeans than in his tribe’s spiritual heritage.
The two Natives are facing away from each other, and I wonder if they are really supposed to be two separate people, or if this is a metaphor for the internal struggle of an individual who’s trying to decide whether to stay true to his family and tribal values or emulate the European customs.
Using Google’s reverse image search, I learned that this peace is called Wi-jún-jon, Pigeon's Egg Head (The Light) Going To and Returning From Washington. It was painted by George Caitlin in 1839. This painting does indeed depict two sides of one person: it’s a “before and after” shot of an Assiniboine Chief who went to visit Washington and returned to his tribe with all kinds of new clothes, accessories and ideas (1).
I don’t feel like the artist is biased one way or another, but it does seem like he’s trying show us something important about individual identity vs. group identity and how our personality can actually change a lot depending on the company we keep. This is as true today as is was at the time of the painting (and throughout all of history). No matter how close and connected you may feel to your family and your oldest friends, there are always new people and new ideas to explore. Identity, personality, and values are malleable, and sometimes new situations will change you a lot more than you’d expect.
 
Work Cited: (1) "Wi-jún-jon, Pigeon's Egg Head (The Light) Going To and Returning From Washington." Smithsonian American Art Museum, n.d. https://americanart.si.edu/artwork/wi-jun-jon-pigeons-egg-head-light-going-and-returning-washington-4317. Accessed 16 December, 2017.