Melt 1 cup of the sugar in saucepan over low heat and cook until golden brown, about 20 minutes. Watch the sugar carefully as it can burn quickly (adding 2 tablespoons of water to the sugar will also help it not burn). Put the caramel into custard cups to cover the bottom.
In mixing bowl add the remaining 1 cup sugar, eggs, and vanilla. Boil the milk, then slowly add to sugar egg mix whisking well. Strain through a fine strainer. Ladle the mixture into the caramel coated custard cups, filling 3/4 full. Put the filled cups into a water bath and cover. Cook for about 50 minutes. Check after 30 minutes. Cool to room temperature.
To serve, run a knife around the edges to loosen and invert onto plates.