Preheat oven to 325°F. Pulse 16 Oreos in food processor until fine crumbs. Mix with 4 tablespoons melted butter and 1 tablespoon sugar. Press firmly into 9-inch pie plate, including up sides.
Bake crust for 15 minutes until fragrant and set. Cool completely on wire rack.
Make brownie layer: Melt 4 ounces bittersweet chocolate, 3 tablespoons butter, 3 tablespoons oil, and 1.5 tablespoons cocoa in microwave at 50% power, stirring frequently.
Whisk together 2/3 cup brown sugar, 2 eggs, 2 teaspoons vanilla, and 1/4 teaspoon salt until smooth. Fold in chocolate mixture, then stir in 3 tablespoons flour just until incorporated.
Pour into crust and bake 15 minutes until edges set and toothpick comes out with thin coating of batter. Cool 60 minutes, then refrigerate 60 minutes until completely chilled.
Make topping: Crush 6 Oreos into bits. Mix with 2 tablespoons powdered sugar, 1 tablespoon cocoa, and 1/8 teaspoon salt. Stir in 2 tablespoons melted butter. Spread on parchment-lined baking sheet.
Bake topping 10 minutes at 325°F, stirring halfway. Cool completely on wire rack, breaking up large clumps.
Make mousse: Melt 6 ounces milk chocolate in microwave at 50% power. Cool to 90-100°F. Heat 3 tablespoons cream to 105-110°F, whisk with 2 tablespoons cocoa.
Whip remaining cream with 2 tablespoons powdered sugar and pinch salt to soft peaks. Fold melted chocolate into whipped cream mixture gently until combined.
Spread mousse over chilled brownie layer to edges. Sprinkle with cooled topping. Refrigerate 3-4 hours or overnight before serving.