According to her father Michael Lohan, it was on the set of this film that Lindsay Lohan overdosed on cocaine for the first time.
Lindsay Lohan would often not show up for filming, calling in sick for a variety of reasons, such as tummy aches, the flu or ear aches. This is reportedly because she was dealing with severe drug addiction at the time of filming, even overdosing on cocaine at one point.
The film was meant to be a starring vehicle for Lindsay Lohan to transition from family fare to adult roles. Its resounding commercial failure and well-publicized production woes centered around Lohan's unprofessional behind-the-scenes behavior marked the beginning of her career downfall.
Instead of utilising a shot from a publicity shoot for the movie poster, a paparazzi shot of Lindsay Lohan (Ashley) in the streets of New York City was used.
Chris Pine (Jake) described working with Lindsay Lohan (Ashley) in this film: "It was a real cyclone of insanity, like being around The Beatles. It was fascinating to watch, and in hindsight it's really a distinct moment in someone's life when you see what's really wonderful about what we get to do and what's really dangerous about it."
Lindsay Lohan: [swap] Lohan has starred in a number of movies that involve some sort of "swapping". In this movie, her character swaps fortune and luck with another man. In Freaky Friday (2003), her character swaps bodies with their mother. In The Parent Trap (1998), she plays both twin sisters who swap lives and pretend to be one another.