Preheat oven to 350 degrees F. Process cookies, 2 tablespoons sugar, and 1/2 teaspoon salt in a food processor until fine crumbs form, 15 to 30 seconds. Add butter and pulse to combine, 5 to 10 times. Press cookie mixture in the bottom and sides of a 9-inch pie plate. Bake, on a baking sheet, until crust is dry and set, 18 to 20 minutes. Cool on a rack.
Place chocolate chips in a bowl. Whisk together cornstarch, egg yolks, 1/2 cup sugar, and 1/4 teaspoon salt in a medium saucepan. Whisk in half-and-half and coffee. Cook over medium low heat, whisking constantly, until thickened and the whisk holds a trail, 6 to 8 minutes. Strain over chocolate chips.
Transfer pudding to a cooled crust and smooth top. Press plastic wrap directly on surface of pudding. Chill, at least 4 hours.
Discard plastic wrap. Whip cream and 2 tablespoons sugar to medium peaks and dollop over chilled pie.