Not sure how well this copied pic will show up, but in case it doesn't, my vote is for the Peace Dollar.
the "draped bust" was modeled after anne willing bingham. http://www.librarycompany.org/women/republicancourt/bingham_anne.htm
I know the Peace Dollar was modeled after the engraver's wife, not sure of the names though. Either that engraver was one lucky fool, or he made a grossly exaggerated version of his wife because he knew he would recieve h**l for eternity from his wife if he portrayed Liberty with a double chin and sagging cheeks. Mercury was modeled after the engraver's tenet I believe? Maybe the tenet's wife...something like that anyways. Illini420, I may be wrong, but if that is a headdress on the Indian Cent, that has to be a male version of Liberty seeing as only males wore headdresses aka warbonnets. I may be wrong though. Krispy, I think you are the winner. That is a nice coin!
I love the Libertad but I think the Dolly Madison commem also should be mentioned, I have tried to take some photos but I none have come out well enough to do the coin justice, The British Britannia coins should also receive some mention
The Indian Head Cent was designed by James B. Longacre. In designing the obverse, Longacre used his daughter, Sarah Longacre, as the model. I believe she was around 12 years old at the time. Here is a clip from the New York Times printed in August 1909, right after the introduction of the Lincoln Cent: http://query.nytimes.com/mem/archive-free/pdf?res=9406E1DF1438E033A25753C2A96E9C946897D6CF