Trivia

The movie is loosely based on the experiences writer Jon Favreau had when he first moved to Los Angeles. 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.

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 dialogue shots later. But director Doug Liman decided instead to film the entire scene on the 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 relationship between the characters played by Jon Favreau and Vince Vaughn mirrors their one in real life. The two are best friends.

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.

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.

The 1964 Convertible Mercury Comet Caliente driven by Vince Vaughn was owned by Jon Favreau.

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 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.

Jon Favreau learned how to swing dance for the movie. For a month, he and Heather Graham rehearsed at her house, and at the Derby. According to Graham in an interview, he already knew how to swing dance and taught her at a dance club they went to. She remembered she would get all sweaty and one night he drove her home in his convertible. She ended up getting really sick from the wind blowing on her.

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 answering machine scene was inspired by a comedy routine by Jeff Garlin.

Director 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."

Jon Favreau stated in The Nineties episode of CNN documentary series The Movies in 2019 that they were inspired by the style of Quentin Tarantino, Kevin Smith and Martin Scorsese.

The word "fuck" is used 95 times, "bitch" is used 31 times, and "asshole" 13 times.

Included among the American Film Institute's 2000 list of the 500 movies nominated for the Top 100 Funniest American Movies.

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 (1990) and this actual shot early in the movie.

Trent's license plate THX 1138 is the same as THX 1138 (1971).

In the bar scene, Rob (Ron Livingston) and Mike (Jon Favreau) order a Dewar's on the rocks and a Budweiser . In Sea of Love (1989), Al Pacino and John Goodman's characters ordered the same drinks.

A Reservoir Dogs (1992) poster can also be seen in one of the scenes.

Charles (Alex Désert) says he didn't get a part on Star Trek: Deep Space Nine (1993). He'd later work with one of its cast members, Terry Farrell on Becker (1998).

Genevieve Tyrrell's debut.

Vernon Vaughn: Vince Vaughn's father plays the lucky gambler at the one hundred dollar minimum blackjack table.

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).