Hull the strawberries and halve them lengthwise. Place the strawberries in a bowl and add the cracked pepper.
In a saucepan, combine sugar and ¼ cup water. Bring to a simmer over medium heat, checking the sugar frequently. Once the sugar begins to melt, stir occasionally and allow to simmer until the liquid turns a deep amber brown caramel, approximately 8 to 10 minutes.Add the strawberries to the caramel and stir into the caramel with a silicone spatula. Transfer to a bowl and mix in the balsamic vinegar. Chill for at least one hour or up to 8 hours.
When ready to serve, layer the ingredients with strawberries, ice cream, strawberries, and finally whipped cream. WE RECOMMEND ICE CREAM MADE IN THE CUISINART ICE CREAM MAKER!
Combine milk, cream and vanilla in a medium saucepan and heat to a slow boil and then reduce to a simmer, allowing to cook for 10 minutes.
Combine eggs, egg yolks and sugar in a medium bowl and mix with a hand mixer at medium speed until mixture is thick and smooth, approximately 2 minutes.
Pour out 1 cup of the hot liquid and with the mixer on low speed, add the cup of hot liquid to the egg mixture in a slow steady stream. When thoroughly combined, pour egg mixture back into the saucepan and stir to combine. Cook, stirring constantly over medium low heat until the mixture coats the back of a spoon. Transfer to a bowl, cover with a sheet of plastic wrap placed directly on the mixture and chill completely.
Once chilled, turn the Cuisinart Ice Cream machine on and pour the mixture into the freezer bowl and mix for approximately 30 minutes.