The scene with Mike and Trent talking in the car on the side of the road was also filmed without a permit (not only could the production not afford one, it is actually impossible for any film production to acquire one to film on that particular highway). Originally they had planned to film just an establishing shot of the two of them in the car, and a shot of them driving away, and then film the dialog shots later. But director Doug Liman decided instead to film the entire scene on the actual side of the road. During filming, several police showed up, and demanded to see a permit. The assistant director held up the police by telling them that they had a permit, but it was in the office across town, several miles away. To get away with the rest of the scene being filmed, Liman had to pretend he was not filming, and didn't look in the viewfinder, and used a microphone inside of the car instead of a boom. Most of the scene was filmed like this, with the police waiting just out of shot, and the two actors and the director pretending they were in fact not shooting.
The movie is loosely based on the experiences writer Jon Favreau had when he first moved to LA. He had just broken up with a long term girlfriend and counted on his friends Vince Vaughn and Ron Livingston to cheer him up. The characters they play in the film are based on themselves.
When director Doug Liman first sent the script to studios, they were interested in financing it. When Liman said he wanted to cast the writer and his friends as actors, the studios backed off. The money to shoot the film was raised independently and Liman cast who he liked.
Some of the bar scenes were shot in actual bars during business hours. A sign was posted near where they were shooting warning patrons that if they came any closer, they would be unpaid extras in the film.
The scene in which Trent angrily yells at Sue, after Sue insulted Mike, was written specifically at Vince Vaughn's request. Vaughn wanted to show that beneath Trent's bravado and swagger, he truly cared for Mike as a friend.
When the main characters are first seen playing video games in Trent's apartment, Reservoir Dogs (1992) and Taxi Driver (1976) posters can be seen on the walls. Later, Trent and Mike argue about Martin Scorsese and Quentin Tarantino, and whether Tarantino copies or pays homage to Scorsese's work. The next scene is a deliberate tribute to Reservoir Dogs' iconic opening scene of the main characters walking in slow motion. Later, the famous Goodfellas (1990) long shot of Henry and Karen walking through the kitchen and into the club is emulated by Trent and Mike.
Since the filmmakers couldn't afford to pay extras, the scenes filmed at parties were filmed at actual parties that were taking place, with many Hollywood up-and-comers in attendance. Among the people in the crowd of the first party (who turn and look at the group as they enter): screenwriters Stephen Gaghan and Mike White.
The shots taken from the hood of the car in Las Vegas were done without a proper permit. The interior of the casino was not the Stardust as the exterior shots imply, but was instead a downtown casino that they paid money to use for the evening.
The crew shot at the Derby with actual customers as unpaid extras. It was awkward for Jon Favreau, who admitted that he had probably (unsuccessfully) hit on some of the women who were being filmed. He also had to tell a man who sat down next to Heather Graham to leave so that the Mike/Lorraine meet cute could be shot.
The release of the film coincided with the swing revival of the 1990s. It increased interest in 1940s culture, Hollywood nightlife, and swing music. Some of the slang used in the film became popular in the years following its release, especially the use of the word "money" as a catch-all term of approval or quality. The exclamation "Vegas, baby!" also became a common quote when referencing the city. The film also gave exposure to the term "Wingman" in its social interaction context.
The scene when the guys walk past the line to get into a bar is resembling the steadicam shot in Goodfellas (1990) when Henry Hill and his wife walk into the restaurant. As a matter of fact they talk about the movie Goodfellas and this actual shot early in the movie.
Due to a lack of money, Doug Liman shot the film on an Aaton 35, a "small documentary-style 35mm camera" that "sounds like a sewing machine." He wrapped a down jacket around the camera, then wrapped a down comforter around the jacket so that it wouldn't make so much noise. Favreau said it was as if he was acting in front of a giant snowball.
The line "You're so money came from a Spike Lee/Michael Jordan commercial. The director kept calling the basketball player "money" in the Nike advertisements. Jon Favreau saw those commercials, but the first time he ever heard someone describe something as "money" in real life was when Vince Vaughn said it on the set of Rudy. Potential investors and studios wanted to get rid of the "money"s, "honey"s, and "baby"s.
Doug Liman felt that the answering machine scene contained too many messages. Jon Favreau was confident that it was the right number of messages-though he admitted, "The crew was not very entertained by it."
Friends of the crew lived in the Hollywood Hills on Temple Hill Drive. Two of the four residents, Wyck Godfrey and Marty Bowen, later produced the Twilight movies. Also in attendance were actors Mike White and Adam Scott, Jon Favreau's downstairs neighbor at the time. Scott had no idea what all the cameras were for.
Nicole LaLoggia: the film's line producer plays two roles: she plays Michelle's voice on the phone, and she appears as one of the bar patrons at the Derby (the brunette sitting to the right of Trent when Mike leaves the table).