Chop almonds, leaving some larger pieces and some very fine pieces.
Place chopped almonds into a small pan and warm on medium heat. Stir occasionally for 3-5 minutes, until the nuts are lightly toasted. You will know the almonds are done when you can smell a faint scent.
Remove from the heat and let the chopped nuts cool completely.
Chop the semi-sweet chocolate bar into fine slivers and place in a heat resistant bowl. (The smaller the chocolate pieces are, the easier they are to melt)
Warm ½ of a cup of whipping cream in the microwave for 45 seconds. The cream should be hot, but not boiling. If the cream bubbles, then it is too hot and needs to cool before using because the excess heat will cause your mixture to split.
Make chocolate ganache.
Combine warm cream and chopped chocolate. Stir until all of the chocolate is melted and completely integrated into the cream. You will have a smooth ganache.
Cool to room temperature before using. (do not chill in the refrigerator because it will be too stiff to fold into the whipped cream.
Make sweetened vanilla whipped cream.
In a large bowl, whip 2 cups of cream, slowly adding sugar, and vanilla.
Whip until stiff peaks form.
Add cooled chocolate ganache to whipped cream and fold together until you have a smooth chocolate cream.
Cut very thin slices off of the end of each pound cake and save for patches and the bottom of the zuccotto.
Next, cut both cakes into 8-10 thin, even slices.
Take the square slices and cut them in half on the diagonal.
Brush one side of the diagonal slices with amaretto.
Line a 10 inch bowl with plastic wrap.
Then, starting at the center, lay the cake pieces in the bowl fitting them together like a puzzle. Fill the bowl nearly to the top.
Fill the cake lined bowl with chocolate cream.
Next, add a layer of toasted almonds.
Use the remaining pound cake to cover the cream and make the bottom of the cake.
Cover the zuccotto with plastic wrap and chill for two hours.
Once the chocolate cream cake is completely chilled, unwrap the bottom of the cake and turn out onto your cake plate.
Mix together powdered sugar and unsweetened cocoa powder and sift over the top of the zuccotto before serving. Slice and serve chilled with a hot cup of coffee.