Just My Luck (2006)

In this pointed nod to Sex and the City, Lohan played a New York gal with great clothes, great gal pals, and a charmed life — until she kisses schlemiel Chris Pine, at which point he suddenly turns lucky while she hits the skids. Sadly, it turned out to be an unlucky role for her — critics savaged it (EW's Owen Gleiberman called it ''vacuously mechanical'') and it flopped at the box office.