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In a large mixing bowl, whip the heavy cream until stiff peaks form. Set aside.
In another bowl, beat the softened cream cheese until smooth, then add powdered sugar and Bailey's Irish Cream, blending until creamy and well combined.
Gently fold the whipped cream into the Bailey's and cream cheese mixture until fully incorporated.
To assemble, layer crumbled chocolate cake at the bottom of each serving glass, followed by a layer of the Bailey's cheesecake mixture, then drizzle with chocolate ganache.
Repeat layers, adding crumbled chocolate cookies if desired, until the glasses are filled.
Top with a final drizzle of chocolate ganache and garnish with chocolate curls or shavings.
Chill in the refrigerator for 1 hour before serving for best flavor and texture.