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Grease a 9-inch pie plate with cooking spray, and set aside. Process chocolate sandwich cookies into fine crumbs in a food processor, about 45 seconds. Microwave ¼ cup butter in a small bowl on HIGH until melted, about 30 seconds. With food processor running, add melted butter; pulse until well combined, about 15 seconds more.
Transfer crumb mixture to prepared pie plate. Firmly press crumbs into bottom and up sides of pie plate in an even layer. Freeze 15 minutes.
Meanwhile, heat cream in a saucepan over medium until steaming; do not boil. Pour hot cream over chocolate chips in a large heatproof mixing bowl; let stand 3 minutes. Gently whisk chocolate mixture until smooth. Cut remaining ¼ cup butter into small pieces, and add to chocolate mixture. Stir until butter is completely melted and incorporated.
Pour chocolate mixture into chilled crust, spreading in an even layer (it will come right up to the top). Chill pie, uncovered, until set, about 2 hours. Top with whipped cream just before serving. Sprinkle with additional crushed cookies.