Prepare a 9-inch round cake pan by lining the bottom and sides with two overlapping pieces of plastic wrap, keeping the sides as smooth as possible. Set aside.
Combine the cream cheese and sugar in a bowl and beat with an electric mixer on medium-high until smooth, about 3 minutes; scrape down the sides of the bowl as needed. Add the cream and vanilla and continue to beat, starting on medium speed and increasing to medium-high, until stiff peaks form, about 2 minutes.
Evenly spread a third of the whipped cream mixture on the bottom of the prepared cake pan. Slice 4 of the bananas into 1/8-inch rounds and arrange half of the slices in an even layer over the cream. Reserve about 5 cookies for garnish, then add a full layer of the cookies on top of the banana slices (each layer will be about 1 heaping cup of cookies), using any broken pieces to fill in the gaps. Repeat with another third of the cream, then a layer of the bananas and cookies. Top with the remaining third cream. Cover the exposed top of the cake with plastic wrap and refrigerate 12 hours or overnight to let the cookies soften.
When ready to serve, unwrap the plastic wrap and invert the cake onto a cake platter; remove pan and plastic wrap. Press the remaining 2 cups cookies all the way around the bottom of the cake in single file. Decorate the top of the cake by standing the 5 reserved cookies in a ring (like animals marching in a circle). Thinly slice the remaining banana and arrange the overlapping slices in a ring along the outer top edge of the cake. Cut the cake into slices with a serrated knife.
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