- 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 beforehand (that was admittedly acclaimed beforehand), but 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: Chloë Sevigny, Alecia Goranson and Allison Folland all auditioned for Brandon before getting cast as Lana, Candace and Kate, respectively.
- The Cast Showoff: Chloë 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).
- Chloë 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. Her blonde hair had to be dyed brown as well.
- Chloë 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.
- Chloë 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. Hilary Swank was paid only $3000 for it, earning $75 a day; as she put it, "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.
- Similarly Named Works: The film shares its title with a 1981 song by The Cure and a British New Wave band who had a 1985 One-Hit Wonder with "I Wanna Be A Cowboy".
- Star-Making Role: Hilary Swank as Brandon Teena. An Oscar win catapulted her to stardom.
- Trans Character, Cis Actor: Trans man Brandon Teena is played by cis actress Hillary Swank.
- 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.
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