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  • Cast the Runner-Up: James Franco was originally attached to play Chuck Traynor before Peter Sarsgaard was cast. He was instead cast as Hugh Hefner.
  • Deleted Role: Sarah Jessica Parker's role as Gloria Steinem was cut in the final version.
  • Dyeing for Your Art: Amanda Seyfried dyed her hair brown for the film. She also underwent a New York accent training.
  • Underage Casting: James Franco, who was in his mid-30s while making this, played Hugh Hefner, who was in his mid-40s during the era in the film.
  • What Could Have Been:
    • Lindsay Lohan was originally cast as Linda in 2010 under the original title Inferno, but was forced to drop out while in court-mandated rehab and was replaced by Kate Hudson, who later dropped out due to her pregnancy. Olivia Wilde was also considered.
    • At some point production of the film somehow bifurcated into another, dueling film to this one that would have retained the Inferno title and starred Malin Ã…kerman as Linda, but production of that film fell apart due to budget issues and was never filmed.
    • James Franco was originally cast as Chuck Tranyor.
    • Demi Moore was supposed to appear in a cameo as Gloria Steinem but dropped out due to health issues. Mary-Louise Parker was considered as a replacement, but Sarah Jessica Parker was cast. Parker accepted the role a week before filming ended, but her scenes did not make the final cut.
    • The ending was originally going to take place in 1984 before it was changed to 1980.
  • Working Title: Inferno.

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