- Actor-Shared Background: Laura Allen attended Wellesley and graduated with a sociology major. And after the film was criticised for its misrepresentation of the college and historical inaccuracies, she expressed regret about appearing in the film.
- Dyeing for Your Art:
- Kirsten Dunst, a natural blonde, darkened her hair to brown.
- Julia Stiles, a natural brunette, lightened her hair to blonde.
- Enforced Method Acting: All the actresses had to go through two weeks of finishing school to prepare for their roles.
- Fake American: Like so many of his other roles, Dominic West is British playing an American.
- Playing Against Type: It was unusual at the time to have Kirsten Dunst play an Alpha Bitch, though admittedly one who goes through Character Development.
- Real-Life Relative: Julia Roberts was married to Daniel Moder, who was the film's second unit director. Dominic West felt quite awkward at filming love scenes with her while he was watching.
- What Could Have Been: It was reported that Chloe Sevigny was turned down for the role of Giselle because she was reeling from the backlash of The Brown Bunny. However, she actually turned the role down in favour of that film, finding Mona Lisa Smile "faux feminist". She didn't regret her decision after the film's critical thrashing. Melanie Lynskey also auditioned for that and the role of Connie.
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