Crush 24 Oreo cookies by using a food processor or by placing them in a zip-top bag and rolling with a pin. Set aside.
In a mixing bowl, beat the softened cream cheese with a hand mixer on medium speed until smooth and creamy.
Gradually add powdered sugar and vanilla extract to the cream cheese, beating until well combined and smooth.
In a separate bowl, whip the heavy cream until stiff peaks form, usually about 3-4 minutes with a mixer.
Gently fold the whipped cream into the cream cheese mixture until fully combined, being careful not to deflate the whipped cream.
In serving glasses or cups, layer the crushed Oreo cookies and cheesecake filling, starting with crushed Oreos followed by a layer of the cheesecake mixture. Repeat layers until glasses are filled.
Top each parfait with some crushed Oreo cookies and a whole Oreo for garnish.
Place the parfaits in the refrigerator for at least 2 hours to chill and set before serving.