In a medium bowl, using an electric mixer, beat the cream cheese until light and fluffy for 1 minute. Beat in 1/2 cup of the half-and-half until smooth, about 1 minute. Beat in the pudding mix and remaining 3/4 cup of half-and-half.
Spoon half of the pudding mixture into dessert cups or small parfait glasses. Sprinkle the cookie crumbs over the pudding.
Set aside 1/2 cup of the cherry pie filling. Divide the remaining cherry pie filling among the cups evenly, spooning over the cookie crumbs. Spoon the remaining pudding mixture over the cherry pie filling. Garnish each dessert cup or small parfait glass with the reserved 1/2 cup cherry pie filling.
Cover with foil and refrigerate for at least 1 hour or up to 2 days.