Finely grind the 9-ounce box of chocolate wafer cookies (about 2 cups crumbs) in a food processor or by placing cookies in a sealed bag and crushing with a rolling pin; set aside.
Set up a double boiler: simmer about 1–2 inches of water in a saucepan over medium-low heat. Place a heatproof bowl over the saucepan so it sits above the water without touching it.
In the heatproof bowl, combine the 4 ounces chopped unsweetened chocolate, 3/4 cup granulated sugar, and 1/4 cup water. Stir constantly until the chocolate is fully melted and the mixture is smooth. Keep the mixture warm over the double boiler.
In a small bowl, whisk the 5 egg yolks until blended.
Temper the yolks: very slowly ladle about half of the hot chocolate mixture into the yolks in a thin stream, whisking constantly to combine and prevent the yolks from cooking.
Return the tempered yolk mixture to the bowl over the simmering water and cook, stirring constantly, for 2 to 3 minutes or until the mixture is slightly thickened. Remove from heat, stir in 1/2 tablespoon Cointreau or Triple Sec, and let the mixture cool to lukewarm.
In a clean large bowl or the bowl of a stand mixer fitted with the whisk attachment, combine the 5 egg whites and 1/8 teaspoon cream of tartar. Whisk on high speed until stiff peaks form, about 5 to 7 minutes.
Fold one-third of the whipped egg whites into the lukewarm chocolate mixture using a rubber spatula to lighten it. Then gently fold in the remaining egg whites until no white streaks remain and the mixture is uniform.
Fold 1 1/2 cups of the cookie crumbs into the chocolate mixture until evenly incorporated.
Divide half of the chocolate mixture among your serving dishes or shot glasses.
Sprinkle half of the remaining cookie crumbs over that layer (the remaining crumbs after folding in 1 1/2 cups will be about 1/2 cup, so use roughly 1/4 cup here).
Spoon the remaining chocolate mixture over the crumbs, then finish with the last of the cookie crumbs (about 1/4 cup).
Refrigerate the assembled desserts at least 2 hours or until set. Just before serving, top each with fresh whipped cream.
Note: this recipe contains raw or undercooked eggs. If you are uncomfortable consuming raw eggs, use pasteurized eggs in the shell or omit.