Begin by crushing the cookies into fine crumbs using a zip-top bag and rolling pin or a food processor, then transfer to a mixing bowl.
In a microwave-safe bowl, melt the semi-sweet chocolate in 30-second intervals, stirring between each, until smooth and glossy. Let it cool slightly.
Using a hand or stand mixer, beat the softened cream cheese until creamy and smooth, about 2-3 minutes.
Add sugar and vanilla extract to the cream cheese and mix until well combined and fluffy.
Pour the melted chocolate into the cream cheese mixture, then gently fold until the mixture is uniform in color and texture.
Mix the crushed cookies into the chocolate-cream cheese mixture, folding gently to evenly distribute the crumbs.
Spread the mixture evenly into the bottom of an 8-inch springform pan, pressing it down gently with a spatula to create a firm base.
Cover the pan with plastic wrap and refrigerate for at least 4 hours, or until the cheesecake is firm and chilled.
Before serving, slice the cheesecake with a sharp knife, serving chilled to enjoy its creamy yet crumbly texture.