Cut the baked and cooled pound cake into bite-size pieces. Set aside.
Place the cherries and brandy in a medium saucepan. Bring to a simmer over medium heat. Cook until the cherries have softened, about 7 minutes. (Don't overcook. You want the cherries to hold their shape.) Set aside to cool to room temperature.
Using an electric mixer on medium speed, beat the cream cheese until smooth. Add the cream and sugar, and mix on low speed until combined. Increase the mixer speed to medium-high and whip until the mixture forms firm peaks.
Place half of the pound cake pieces in 8 serving cups or glasses. Alternatively, place half the pieces in the bottom of a 2- to 2 & 1/2-quart bowl.
Top the cake with half of the cherries and their juices. Sprinkle half of the almonds and half of the chocolate. Top with half of the cream cheese mixture. Repeat the layers. (I reserved some cherries, almonds, and chocolate for garnish.)
Cover and refrigerate at least 3 hours before serving.
Notes
I made a half recipe in a standard 9"x 5" loaf pan, substituting almond extract for the vanilla. If you prefer, you can use a store-bought pound cake.
I recommend switching your regular mixer beaters to a whisk attachment for whipping the cream.
I used 6-ounce cups and overfilled quite a bit. 8-ounce cups/glasses/dishes would work well, too.