- Blooper: By the crew, in one scene Matthew McConaughey's character sits in front of a poster of a Lamborghini Aventador, a car from the 2010's, which makes no sense considering that the movie takes place in the 1980s.
- Career Resurrection: For Matthew McConaughey, as with his role he took home a Golden Globe and an Oscar. Roles in bigger films (The Wolf of Wall Street, Interstellar, Sing, The Gentlemen) came to McConaughey after this film became a critical darling.
- Cross-Cast Role: Cisgender man Jared Leto plays Rayon, a transgender woman. His performance garnered him critical acclaim and numerous accolades including an Academy Award, though members of the LGBT community criticized the casting choice as perpetuating the harmful stereotype that trans women are men in drag.
- Dyeing for Your Art: Both McConaughey and Leto lost a considerable amount of weight to play HIV patients.
- Method Acting: Jared Leto stayed in character throughout filming. At one point, he went grocery shopping in character at a local Whole Foods, where he received numerous stares.
- Science Marches On: AZT, the drug Ron rejects, is still used today in lower, less toxic doses and in combination with other drugs. On the other hand, many of the drugs Ron sells are no longer used at all due to THEIR toxicity.
- Trans Character, Cis Actor: Cisgender actor Jared Leto plays the transgender woman Rayon.
- What Could Have Been:
- Ryan Gosling, Woody Harrelson and Brad Pitt were considered for the part of Woodroff, in earlier versions of the film. Dennis Hopper was even slated to be behind the camera at one point.
- Hilary Swank was cast but she dropped out due to scheduling conflicts.
- You Might Remember Me from...: It might even involve reading the credits to notice that's Griffin Dunne from An American Werewolf in London and After Hours under all that hair as Doctor Vass.
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