10. The Last Tycoon (Directed by Elia Kazan, 1976)
So many movies about Hollywood are revenge-tragedies, or revenge-fantasies, usually featuring a disgruntled screenwriter who somehow seeks vengeance against his or her unfeeling bosses. The Last Tycoon is a variation on this theme, as it is based on the great F. Scott Fitzgerald’s last and unfinished novel, which was a semi-fictional, semi-autobiographical account of his own unhappy experiences in Hollywood.
The titular “Tycoon” is Monroe Stahr, a successful studio boss played by Robert De Niro who is financially and artistically successful, but personally bereft; devastated by the loss of the only woman he had ever truly loved, he finds himself obsessed with another young woman who reminds him of her. She becomes the one thing, or rather person, he cannot have and, distracted by his longing for her, he gradually loses control of the studio.
The Last Tycoon is an elegy to a Hollywood that was already long-gone by the 1970s, when the film was made, but its legacy remains, particularly in one scene that may just be the single best scene about film-making ever made, in which De Niro attempts to explain to a truculent theatre director, played by Donald Pleasance, exactly how movies work. He literally acts out, in silent movie-style, the scene he describes, in the process showing exactly how the strange and nebulous art of screenwriting (an art that even the great F. Scott Fitzgerald could not master) works.