Place 1/4 cup sugar in small, heavy bottomed sauce pan and turn heat to medium high. Cook until sugar melts and turn a nice a shade of brown. Immediately pour into 4 ramekins, swirling to distribute. Preheat oven to 300 degrees.
Combine remaining sugar with 2 eggs and whisk until dissolved. Add milk and vanilla and whisk briefly.
Place ramekins in baking dish with about 1/2 inch of water surrounding. Cover pan tightly with aluminum foil and bake for 45 minutes. Custards should be somewhat giggly. Remove ramekins and let cool. Invert on plates to serve.