- Actor-Inspired Element: Peter Sarsgaard felt the need to make John more charismatic than he was described in the script - to make it believable that everyone would want to hang out with him.
- Breakthrough Hit: Kimberly Peirce had only directed one short film (that was admittedly acclaimed beforehand). This suddenly put her on the map as a director.
- California Doubling: Despite taking place in Nebraska, the "night in the big city" montage was filmed in, and features the prominent buildings of, downtown Dallas.
- Cast the Runner-Up: ChloŽ Sevigny, Alecia Goranson and Allison Folland all auditioned for Brandon, before getting cast as Lana, Candace and Kate respectively.
- The Cast Showoff: ChloŽ Sevigny performs "The Bluest Eyes in Texas" in the karaoke scene.
- Cross-Cast Role: Cisgender female Hilary Swank plays transgender male Brandon. Due to the lack of openly trans actors at the time (and Hollywood's hostility to them), this was probably to be expected.
- Darkhorse Casting: Most high profile actresses avoided the project because of the stigma associated with an LGBT role, so Kimberly Peirce cast an unknown as Brandon.
- Dawson Casting: Hilary Swank was a couple of years older than the character she played, though she lied to say she was the same age (claiming it's what Brandon would have done). Chloe Sevigny was also in her mid-twenties playing Lana at nineteen.
- Disowned Adaptation: Lana Tisdel sued the filmmakers for defamation, enraged that she was depicted as "white trash" and an alcoholic. She called it "the second murder of Brandon Teena".
- Dyeing for Your Art:
- Hilary Swank lived as a man to prepare for her role as Brandon Teena, including cutting her hair short and wrapping her breasts. She also had to lose weight and stuff a sock down her pants. Swank's blonde hair had to be dyed brown as well.
- ChloŽ Sevigny dyed her blonde hair red because Lana Tisdel is a redhead in real life.
- Executive Meddling: The film was threatened with an NC-17 rating - not for the violent shot through the head - but for Lana's orgasm lasting too long.
- Method Acting:
- Hilary Swank lived as a man for an entire month beforehand, wrapping her breasts and putting a sock down her pants. She apparently fooled her neighbours, who assumed that the person leaving her home was her brother visiting.
- Chloe Sevigny likewise watched loads of videos of the real Lana to properly get a sense of her mannerisms.
- No Budget: Made for only $2 million. As Hilary Swank put it (she was paid only $3000 for it, earning $75 a day) - "I had an Academy Award but no health insurance."
- Separated-at-Birth Casting: Alicia Goranson was cast as Candace precisely because she looked like her real life counterpart Lisa Lambert.
- Star-Making Role: Hilary Swank as Brandon Teena. An Oscar win catapulted her to stardom.
- What Could Have Been:
- The film was going to be shot on location in Falls City, but budget constraints led to Dallas doubling for it.
- Drew Barrymore was attached for a while, and Kimberly Peirce had envisioned Jodie Foster as Lana. The latter role was also offered to Reese Witherspoon and Sarah Polley before Chloe Sevigny was cast.
- Diane Keaton considered directing.
- Initial drafts of the script focused more on All She Wanted - a biography of Brandon's final weeks - and would feature more of his family members and ex-girlfriends. Kimberly Peirce chose to focus more on the relationship with Lana, finding it "a great love story" (which by contrast, was barely mentioned in the book).
- The rape scene was longer and more graphic, showing that Brandon was raped repeatedly throughout the night. It had to be reduced after negative responses from test audiences.
- The film's low budget meant that two real life figures had to be left out of the story - Lana's real life sister Leslie and her boyfriend Philip Devine. He was a black, disabled man who was murdered on the same night as Brandon.
- Working Title: Take It Like a Man.
Trivia / Boys Don't Cry