Microwave 1/2 cup cream at HIGH 30 seconds to 1 minute or until hot (do not boil). Place bittersweet chocolate in a large bowl. Pour hot cream over chocolate, and stir until smooth. Repeat procedure with 1/4 cup cream and white chocolate. (If chocolate does not melt completely after stirring, microwave at HIGH for 10-second intervals just until chocolate is melted and mixture is smooth.) Stir 1/2 tsp. vanilla into each chocolate mixture until well blended. Cool 20 minutes.
Meanwhile, let 2 1/2 cups cream stand at room temperature 20 minutes.
Beat 1 1/2 cups cream at medium-high speed with an electric mixer until medium peaks form. Gently fold one-fourth of whipped cream into cool bittersweet chocolate mixture. Repeat procedure with remaining whipped cream.
Beat remaining 1 cup cream at medium-high speed until medium peaks form. Gently fold one-fourth of whipped cream into cool white chocolate mixture. Repeat procedure with remaining whipped cream.
Crush 6 to 7 cookies to equal 1/2 cup crumbs. Sprinkle on bottom of a lightly greased 9-inch springform pan. Spread half of bittersweet chocolate mixture over crushed cookies in pan. Arrange cookies around sides of pan (about 19 cookies). Spread white chocolate mixture over bittersweet chocolate mixture.
Crush remaining cookies, and sprinkle over white chocolate mixture in springform pan. Drizzle with liqueur, if desired. Spread remaining bittersweet chocolate mixture over crushed cookies. Cover and chill 8 to 24 hours.
Remove sides from pan. Mound raspberries in center of trifle; brush with Raspberry Glaze. Serve immediately.
Note: For testing purposes only, we used Ghirardelli 60% Cacao Bittersweet Baking Bars, Ghirardelli White Chocolate Baking Bar, Pepperidge Farm Distinctive Entertaining Cookie Collection, and Godiva Mocha Liqueur.
Raspberry Glaze: Combine 3 Tbsp. seedless raspberry jam and 2 tsp. water in a small glass bowl. Microwave at HIGH 10 to 15 seconds or until smooth.