- Awesome, Dear Boy: Robert Downey Jr. was attracted to the film when he heard Keanu Reeves was going to star and Richard Linklater to direct. He thought that the script was the strangest one he had ever read. Woody Harrelson and Winona Ryder agreed to appear in the film based on the script.
- Doing It for the Art: Keanu Reeves and Winona Ryder agreed to work for the Screen Actors Guild scale rate plus any back-end profits.
- Reality Subtext: Robert Downey Jr. and Woody Harrelson in a film about drug addicts.
- Release Date Change: Originally, the film was supposed to be released in September 2005.
- Saved from Development Hell: Terry Gilliam originally wanted to adapt the book in the early nineties.
- Typecasting: The whole cast fits this trope. Who better to play a closed circle of stoners who sit around and shoot the shit than Woody Harrelson, Robert Downey Jr., Keanu Reeves, Winona Ryder and Rory Cochrane of Dazed and Confused fame. You also have crazy conspiracy theorist Alex Jones making a cameo as a crazy conspiracy theorist. Honestly, it wouldn't be surprising if the psychiatrists in the movie were actually accredited psychiatrists. Could also be seen as Meta Casting.