- The Cast Show Off: Kristen Stewart co-wrote "Tracy's Song".
- Dyeing for Your Art: Emile Hirsch lost 40 pounds for his role as Chris.
- Harpo Does Something Funny: Zach Galifianakis was told to improvise all his lines, as his character didn't have any in the original script.
- No Stunt Double: Emile Hirsch did his own stunts.
- Playing Against Type:
- Vince Vaughn, though portraying a gregarious fast-talker akin to some of his other characters, does so in a more dramatic context.
- Catherine Keener, usually known for playing neurotic or hard-nosed characters, playing the warm-hearted, free-spirited hippie Jan.
- What Could Have Been:
- Sean Penn once envisioned Leonardo DiCaprio as Christopher McCandless and Marlon Brando as Ron Franz when he first became interested in making the film.
- Shia LaBeouf was considered for Christopher.
- Daveigh Chase, Amber Heard and Evan Rachel Wood auditioned for Tracy.
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