Put the cream and sugar in a mixing bowl, and whip with a hand mixer until soft peaks form. (Mix in espresso powder or coffee powder to your whipped cream for extra coffee flavor!)
Scoop 3 small scoops of gelato into each of 4 parfait or Irish coffee glasses. Pour 1 shot of espresso over each serving. Crumble some cookie pieces over the ice cream. Top with a dollop of whipped cream and more crushed cookies.