In a small bowl, mix the espresso, brandy, and sugar. Set aside.
In a medium bowl, beat together the yogurt, ricotta cheese, and pie filling syrup. If you do not have beaters, you can combine the yogurt, ricotta cheese, and syrup in a blender and then add to a bowl. Add in the cherries and chocolate chips. Fold in the whipped topping, gently, until incorporated.
Prepare the individual bowls. Dip the ladyfingers or vanilla cookies in the espresso mixture, just long enough to absorb the liquid but not too long that they become soggy. Layer them at the bottom of the bowls. Cut them to pieces if you have to, to make them fit.
Spoon the creamy yogurt mixture on top of the ladyfingers or vanilla cookies and cover them. Repeat the layering. The last layer should be the yogurt mixture.
Garnish with the remaining cherries and chocolate chips.
Cover with a plastic wrap and refrigerate for at least 2 hours before serving.