Trivia: Many of the director's own family members appear in cameos in the film. One of the more obvious instances is the suspicious cashier at the convenience store, played by the director's mother.
Trivia: Throughout the movie, references to the Grimm fairy tales can be seen everywhere. The 'pedophile scene' was supposed to be heavily influenced by the Hansel and Gretel fairy tale. The door mat is German for "Hansel and Gretel" in mixed up letters. Also, the name on the medicine bottle Oleg grabs is Edele Hansel. The prostitute is supposed to be the Blue Fairy, Oleg being captured by the homeless man is Little Red Riding Hood. Above all, the town's name, though never stated, is Grimley. Watch the credits for an animated visual.
Trivia: 1620 Racine is the same block as in the movie The Untouchables. The address where Sean Connery is killed is 1634 N Racine.
Trivia: This film was filmed back-to-back with Flags of Our Fathers, a movie from the American perspective of the battle of Iwo Jima.
Trivia: Maya Rudolph, who plays the pregnant character Molly, was actually pregnant during the filming of the movie.
Trivia: Red Dawson has a cameo as the head coach of Morehead State.
Trivia: In the epilogue, all of the characters' fates are accounted for, except for the fact that Noah Dietrich's account of Howard Hughes' life, which formed the "rough draft" of Clifford Irving's hoax, WAS published (presumably after considerable editing) as a mass-market paperback after the scandal struck.
Trivia: Matt Damon is only eleven years older than Eddie Redmayne, who plays his on-screen son.
Trivia: The four customers who are seated behind Sheryl and Richard during the diner scene are the parents of the movie's directors Jonathan Dayton and Valerie Faris.
Trivia: Marilyn Dean tells Brooke (Jennifer Aniston) to go see her personal waxer at the spa and to ask for the "Telly Savalas". Telly Savalas was Jennifer Aniston's godfather. (00:56:00)
Trivia: As a bit of an easter-egg, Mel Gibson included a single-frame of an actor dressed as Wally/Waldo from the "Where's Wally/Waldo?" book series in the theatrical version of the film. It was reportedly seen as being in poor taste, so it was removed from the initial DVD release. However, he was allegedly added back into the film for the Blu-Ray release.
Trivia: At Frankie's house, when some girls visit during the daytime, Frankie turns to Zack and calls him 'Yankele'. Yankele is a Yiddish [German-Hebrew] affectionate version for Yaakov, or Jacob, since Zack is Jewish.
Trivia: This movie was filmed back-to-back with Letters from Iwo Jima, a fictional account of the battle of Iwo Jima that looks at it from the Japanese soldier's perspective.
Trivia: Outside the Port Authority terminal is a statue of Jackie Gleason as Ralph Kramden from "The Honeymooners." According to Oliver Stone in the audio commentary, that statue actually exists.
Trivia: At the time of the filming, the St. Charles Streetcars were not running 100%. When they show the Canal St Car, one sense that shows the car running on the right side tracks toward the camera, it's actually on the wrong side. Later when he's going to her apartment, one shot shows the streetcar running on the right side tracks (as the norm), and the trolley poles are up. Later when he gets off the car, it's on the opposite side, wrong direction, rear pole is down, and he gets out through the rear door as if it was main door.
Trivia: Included in the film's soundtrack are the songs from performers/composers who have themselves committed suicide, such as Joe Meek and Rozz Williams.
Trivia: Although Adrian Brody was officially the star of "Hollywoodland," his character (private detective Louis Simo) was a completely fictional role in the movie. Virtually all of the other characters in the film are based on real people, but there never was a Louis Simo, and he's not based on any actual person (s). George Reeves' mother did hire an attorney and a detective agency in real life; however, "Hollywoodland" director Allen Coulter said that the character of Louis Simo wasn't even partially based on anyone in real life.
Trivia: The spacesuit that the character Charles Farmer wore is a replica of the pressure suit used by the Mercury 7 astronauts.
Trivia: Anytime one of the characters click on "Do you want to meet a ghost?", they all click the "to".