There have been many previous attempts to get the film made since the 1950s. Author Jack Kerouac sought to have himself play Sal Paradise opposite Marlon Brando as Dean Moriarty. In 1990, Francis Ford Coppola was set to direct with Ethan Hawke as Sal, Winona Ryder as Marylou and Brad Pitt as Dean. Later, Joel Schumacher was attached to direct with Billy Crudup as Sal and Colin Farrell as Dean. Gus Van Sant was later involved as a potential director.
Because Amy Adams had just become a mother when shooting began and she's playing a drug addict on the movie, she decided to not use much make-up and incorporate her natural tiredness due to having a baby to the role.
Kristen Stewart agreed to a salary less than $200,000 after the film's budget was drastically cut. Stewart remained committed to the role of Marylou out of her love for the original novel by Jack Kerouac.