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This chapter examines the wish-fulfillment fantasy embedded in Wise Guys (1986). As a gangster comedy, Wise Guys is best appreciated as a happy alternative to Scarface (1983), as things that went wrong in that film—and in De Palma's life—now go miraculously right. At the same time it also features what De Palma has described as “the family as a structure involving manipulation and destruction of the individual”—embodied in the relationship of the film's two protagonists, small-time mobsters Harry (Danny DeVito) and Moe (Joe Piscopo), to crime boss Castelo (Dan Hedaya). Though Harry and Moe seek his approval, godfather Anthony Castelo is cold and distant toward them, much as De Palma felt that his own father, Anthony, often behaved toward him and his brothers.

This introductory chapter explains the coverage of this book, which is about Hollywood historical films. This book provides commentaries on historical films produced in the U.S. from 1931 to 1942 and argues that a filmic writing of American history flourished in Hollywood during this period. It reviews several historical films including Cimarron, Scarface, and Gone with the Wind.

This chapter provides commentaries on the 1932 historical film Scarface. This film was directed by Howard Hawks and was based on Armitage Trail's novel of the same title which was about the life of Chicago gangster Al Capone. This chapter discusses the trend in contemporary crime and fictional gangster film during this period and explains the processes and challenges encountered in the production of Scarface.

This chapter chronicles De Palma's switch in genres following the poor box office performance of Blow Out (1981)—Scarface (1983). De Palma had considered that gangster films would be more commercially viable, and found some freedom in delving into the kind of films that were not quite like, in his own words, “these Brian De Palma movies.” Scarface is set in 1980, and Tony Montana (Al Pacino) is one of the Cuban evacuees who journey to Florida as part of the Mariel Boatlift when, along with many law-abiding citizens, Fidel Castro also unloaded some criminals from his jails. Among other things, the film itself can be said to echo De Palma's own inner conflict in succumbing to the money-grubbing nature of the film industry while at the same time criticizing the dangers of such greed.

This chapter examines De Palma's departure from Scarface (1983) in Carlito's Way (1993). At first hesitant to make another Scarface, he was eventually persuaded to do the film: “What I liked about it was it was completely different from Scarface. Where Tony Montana is cold, calculating and willing to do anything to rise to the top, Carlito is at the other end of the spectrum: he's trying to reform. He slowly gets dragged back into the game.” The new film's many references to Scarface also help the viewer mark the differences separating them, as do their stylistic differences. The chapter explores Carlito's character throughout the film and the doubts it raises about whether or not Carlito is backsliding into his old ways—perhaps in the same way that Carlito's Way is turning into another Scarface.

This chapter gives background on the pre-Code era of filmmaking, along with Howard Hughes’s entry into the film industry and his decision to make Scarface. The chapter also covers Dvorak’s relationship with actress Karen Morley and how this bond led to Ann being cast by director Howard Hawks in Scarface, thus launching her career as a dramatic film actress.

In this chapter, Hawks tells of the production of Scarface and working with Howard Hughes and Paul Muni. He discusses the censoring of the film, rights ownership, and the redistribution of the film. He describes his use of the Chicago newspaper wire and convict writers, and his dealings with gangsters, including Al Capone himself. Hawks also details his experiences with Hughes after Scarface, as Hughes was becoming a director in his own right.

This chapter talks about the texts around 1979 in Miami and the overlapping histories of the illicit drug trade, African American uprising, and Mariel migration. A response to Mariel appeared in the 1983 film Scarface, which put its lead actor, Al Pacino, in brownface, as the Mariel migrant Antonio Montana. This was a minstrel moment, whose lineage involves the Jewish American Paul Muni's Italianface performance in the 1932 version of the film, as well as African American and Afro-Cuban American appropriations of Montana in rap music. The chapter elaborates on how these acts of Scarface minstrelsy, the seeming idolizing of the drug-violence corpse of Antonio Montana, commemorate other corpses as well, such as that of African American Arthur McDuffie—whose murder by the police led to the 1980 African American riot.