To a large mixing bowl, add cream cheese and powdered sugar. Beat on medium with a hand mixer until creamy.
In a small microwave-safe bowl, add in the semi-sweet chocolate. Microwave for 30 seconds and stir. Repeat the microwaving and stirring until the chocolate is completely melted.
Pour the chocolate into the mixing bowl with the cream cheese.
Add the vanilla extract. Beat until the chocolate and vanilla extract is incorporated. Scrape down the sides and beat in anything that hasn't been incorporated yet.
In a separate bowl, add in the whipped cream. Beat on medium until stiff peaks form. Scrape the whipped cream into the bowl with the cream cheese. Set the whipped cream bowl aside for a later use.
Beat the whipped cream into the cream cheese mixture until combined.
Add into a disposable piping bag using a spatula and set aside.
Add the chocolate chips and 2 tablespoons of heavy cream into a microwave-safe bowl. Microwave for 30 seconds and stir. Repeat microwaving and stirring until the chocolate is smooth. Let cool to room temperature.
Add the remaining heavy cream into the same bowl we used before for whipped cream. Beat on medium until stiff peaks form.
Add the cooled chocolate mixture to the whipped cream. Fold in until combined.
Add the chocolate whipped cream into a piping bag fitted with the 1M piping tip. Set aside.
Add the chocolate creme filled sandwich cookies into a food processor and pulse them until their crumbs. You can also just add them to a storage bag and beat them with a rolling pin until they're crushed.
Add the cookie crumbs into the bottom of two glasses. Add a layer of chocolate cheesecake mousse. Add a layer of chocolate syrup. Repeat each layer one more time.
Add a swirl of whipped cream to the top of the trifles. Sprinkle on some chocolate curls. You can also use cookie crumbs, chocolate sprinkles, red heart sprinkles, etc.