In a small saucepan, combine 1 cup chocolate chips and ½ cup of the heavy cream over medium-low heat, stirring frequently until chocolate chips are completely melted and mixture is smooth.
Remove from heat and pour into a heatproof bowl. Stir in vanilla extract.
Allow mixture to cool completely before continuing.
In a clean, medium-sized bowl, use an electric mixer to beat remaining 1 ½ cups heavy cream to stiff peaks. Set aside.
In bowl of stand mixer, combine cream cheese and (cooled) chocolate mixture, stirring until completely combined.
Gradually add powdered sugar until completely combined. Scrape down sides of bowl as needed.
Stir in vanilla extract and 1 ½ cups of the Oreo crumbs (reserve remaining crumbs to sprinkle over tops of shooters).
Fold in whipped cream and then stir on low-speed until completely combined.
Set out 24 disposable shot glasses.
Pour mixture into large Ziploc bag, snip off one corner and pipe filling into shot glasses, filling about ¾½ full.
Cover tops of each shooter with remaining Oreo crumbs.
Prepare Milano cookies buy using black frosting to write "RIP" on upper half of cookie.
Press Milano cookies firmly into half of the shooters so that only the half of the cookie reading "RIP" is protruding (like tombstones).
Prepare whipped cream ghosts by combining heavy cream, powdered sugar, and vanilla in clean medium-sized bowl and whisking until stiff peaks form.
(You may instead skip this step and use Cool Whip).
Pour whipped cream (or Cool Whip)into large piping bag fitted with a large round tip and pipe ghost-shaped swirls on top of the remaininghalf of dessert shooters.
Use black frosting to gently draw eyes and mouths on ghosts
Serve & enjoy!
I ALWAYS BUY MY SHOT GLASSES HERE FROM AMAZON (affiliate link) *You may substitute 12 oz of Cool Whip for the 1 ½ cups whipped heavy cream in the filling (you will still need the ½ cup for melting with the chocolate). **You can substitute additional Cool Whip to make these ghosts, if you prefer. This recipe makes enough for about 10-12 ghosts and is assuming you will top the rest of the shooters with cookie tombstones. You may double the recipe if you would like them all to be topped with ghosts.