| 1 | * TheCastShowOff: Creator/KristenStewart co-wrote "Tracy's Song". |
| 2 | * DyeingForYourArt: Creator/EmileHirsch lost 40 pounds for his role as Chris. |
| 3 | * HarpoDoesSomethingFunny: Creator/ZachGalifianakis was told to improvise all his lines, as his character didn't have any in the original script. |
| 4 | * NoStuntDouble: Creator/EmileHirsch did his own stunts. |
| 5 | * PlayingAgainstType: |
| 6 | ** Creator/VinceVaughn, though portraying a gregarious fast-talker akin to some of his other characters, does so in a more dramatic context. |
| 7 | ** Creator/CatherineKeener, usually known for playing neurotic or hard-nosed characters, playing the warm-hearted, free-spirited hippie Jan. |
| 8 | * WhatCouldHaveBeen: |
| 9 | ** Creator/SeanPenn once envisioned Creator/LeonardoDiCaprio as Christopher [=McCandless=] and Creator/MarlonBrando as Ron Franz when he first became interested in making the film. |
| 10 | ** Creator/ShiaLaBeouf was considered for Christopher. |
| 11 | ** Creator/DaveighChase, Creator/AmberHeard and Creator/EvanRachelWood auditioned for Tracy. |
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