Dolley Madison actually looks a lot younger, and is depicted more flatteringly, than the ladies on the first two First Spouse coins. I wonder if the better treatment she got is because her name is more well-known than the other first ladies, and people have a good feeling in general about her name because of the line of sweet treats named after her. Seriously, she was a well-beloved first lady in her own time, and a leading American socialite for nearly fifty years. Dolley has always been well-liked, and perhaps that is why she fared better than others in the artistic remembrance of her that she enjoys on this coin.
The obverse designer and engraver of the Dolley Madison coin was Don Everhart, a U.S. Mint sculptor-engraver. Take a look at the James Madison Presidential Dollar.
The obverse designer and engraver of the Dolley Madison coin was Don Everhart, a U.S. Mint sculptor-engraver. Take a look at the James Madison Presidential Dollar.

