Pacino recalls how, after winning his Oscar, he continued to make interesting films like Carlito and Heat. In this era he befriended actors such as Johnny Depp, Dustin Hoffman and Robert DeNiro. Pacino fondly recalls filming Heat with DeNiro, with whom he had a fantastic working relationship. 

At this time, Pacino began directing Looking for Richard, his film about Richard lll. He remembers this project as one of the happiest and most fulfilling of his life. He was then thrilled to play Shylock in the film version of The Merchant of Venice before reprising the role on stage as well. One of his co-stars on stage was Lily Rabe, the daughter of Pacino’s former girlfriend Jill Clayburgh.

In his 60s Pacino moved from New York to LA to be closer to his young children. A New Yorker at heart, Pacino had some trouble adjusting to LA life. He continued to work in film, starring in Ocean’s Thirteen and Wilde Salome. 

With money coming in, Pacino was spending liberally without thinking of the consequences. Eventually, Pacino realized that his accountant was giving him poor advice and was breaking the law. Pacino regrets his lack of oversight into his finances, recalling how he was astonished to find himself broke.