Penelope Ann Miller plays Carlito's girl friend Gail. They broke up when Carlito was sentenced to 30 years in prison, and lost all contact. However, Carlito surprises her when he gets out of jail after only 5 years. They rekindle their lost love. Carlito's relationship with Gail gives him even more of an incentive to stay out of trouble.Miller gained stardom as the leading lady in several films in the late 80's and early 90's. Most notably were The Freshman, Kindergarden Cop, Other people's Money, and Chaplin. She has slowed down her film work as of recently. She gained prominence as a fashion model in the mid-1980's.
Her latest films released were The Relic and The Last Don
Her current project is LITTLE CITY, also starring Jon Bon Jovi.