On June 16, 1959, George Reeves (Ben Affleck), the Man of Steel on TV's popular Adventures of Superman series, is found dead in his Hollywood Hills home with a bullet in his head. One paper flashes the headline "Superman Kills Self" but others in Tinsel Town believe that he may have been murdered. Louis Simo (Adrien Brody) is a young hustler who is near the end of his rope financially. He pretends to be a private eye and is spying on a woman whose husband believes she is cheating on him. Simo is separated from his wife (Molly Parker) but still sees his son (Zach Mills) who, like many other children, has been genuinely traumatized by the death of Superman, their only hero.

Seeing a chance to gain some media exposure for himself as well as a nice payday, Simo convinces Reeves's estranged mother (Lois Smith) to begin her own investigation into the death of her son. He believes that the police are on the wrong track and that there has been a cover-up of a murder by powerful people in Hollywood. One suspect is Reeves's fiancée, Leonore Lemmon (Robin Tunney), a tough party girl and actress the middle-aged Reeves found appealing. Another is Edgar Mannix (Bob Hoskins), an MGM studio executive whose wife Toni (Diane Lane) had had an affair with Reeves and had set him up in his luxurious home.

The multi-layered storytelling in this film noir reveals that director Allen Coulter has great admiration for both Chinatown and L.A. Confidential as explorations of crime, sexuality, power, wealth, and betrayal. He draws out some top-drawer performances from Adrien Brody as the wily private eye, Diane Lane as the older mistress, Jeffrey DeMunn as the actor's pr agent, Bob Hoskins as an MGM executive, and Joe Spano as his right-hand man.

But perhaps the most effective and intriguing theme in Hollywoodland is that Reeves and Simo, both fed by the underground stream of the Hollywood dream, are disappointed with themselves and what fate has brought them. This emotion and its downward arc are the price we pay for high expectations and a belief in the exaggerated hype of success and fame. Reeves came to California as a young man and landed a part in one of the most famous movies of all time Gone With the Wind, but his phenomenal luck faded quickly. When Toni arrives in his life, she provides him with the comforts he needs and believes he deserves. She is thrilled about his part in the Superman series but he despises it and comes to detest the kids who adore him as their superhero. The actor is so identified with this TV character that he can't find work in other films. Eventually, Reeves comes face-to-face with middle-age disappointment, and it is not a pretty picture.

Simo's illusions of grandeur and success fare poorly as he tries to discover the truth about Reeves's death. He is brutally beaten and left with only pieces of the puzzle but no conclusive idea of what really happened. The vulnerability of these two characters is not ridiculed but presented with shadings that enable us to empathize with their yearnings and understand the sadness that comes with disappointment.

Special DVD features include a commentary by director Allen Coulter; "Recreating Old Hollywood"; "Behind the Headlines"; "Hollywood Then and Now"; and deleted scenes.