After seeing a rough cut of the film, Burt Reynolds regretted making it. He fired his agent for recommending the role to him, and did not participate in promotional interviews. Reynolds ended up winning a Golden Globe for the role, and being nominated for an Academy Award for his performance. Despite being a front runner for the latter, it was widely rumored that he did not win because he had distanced himself from the movie earlier.
Amber Waves's custodial problems were inspired by porn star Veronica Hart, who plays the judge during the scene in which Amber and her husband are arguing in court about their son.
Burt Reynolds hated the idea of doing a movie promoting the porn industry, and turned the Jack Horner role down seven times. He also felt like he was selling out, and letting his old fans down. After angrily telling Paul Thomas Anderson the last time the part was offered he wasn't interested, and to leave him alone, Anderson told him if he could carry that attitude with him to the role, he would be nominated for an Oscar. He subsequently chose to do the film after his agent pushed him to, because he hadn't had a decent offer in a long time. He was later nominated for Best Actor in a Supporting Role.
Leonardo DiCaprio was originally offered the role of Dirk Diggler. He liked the screenplay, but turned it down because he had already signed on to do Titanic (1997). DiCaprio suggested Mark Wahlberg for the role. Ironically, Wahlberg had been considered for Jack Dawson in that film but declined in order to do this film instead.
Paul Thomas Anderson simulated the dialogue in the fake porn movies by adapting actual dialogue from real porn movies. He said he did it so people could not say the porn dialogue "sounded fake."
Paul Thomas Anderson: [long take] The opening scene is three minutes long, taken in a single camera shot, beginning in the street where Jack Horner and Amber Waves drive up and following them as they get out of the car and walk into a nightclub. Most of the characters are introduced in that shot.
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