- Old Shame: For Tom Hardy, who said that he had no plans to ever do a romantic comedy ever again after this. Reese Witherspoon has also disowned the film, along with the rest of her catalogue between 2007-2012.
- Saved from Development Hell: The movie was in development since at least 1998, and went through untold amounts of rewrites and numerous cast changes.
- Star-Derailing Role: This movie completely destroyed Reese Witherspoon's career as a leading lady, as ever since, outside of leading films she produced herself, she's been in supporting roles and cameos.
- Throw It In!:
- Most of Chelsea Handler's lines were ab-libbed, including the mention of Cheetos and Mike and Ike.
- The lady's bathroom scene was improv on the part of Reese Witherspoon... except the bit where she leans into the mirror and says "Has that been on my teeth the whole time?" They had filmed an eating scene earlier in the day, and she had a piece of schmutz stuck in one of her front teeth, and her reaction to seeing it was real. They used it in the film anyway.
- What Could Have Been:
- Writer Larry Doyle in this post states that as bad as the final product was, it could've been far worse, as the draft he had to rewrite in 1998 had a man screaming on a wrecking ball, Subverted Immodest Orgasm jokes and "urban" slang straight from a middle-aged white man, and had to rewrite it in six weeks.
- The original script (written in 1997) was a mix of romantic comedy and a High Concept disaster movie and featured every single monument in New York City getting destroyed. Not surprisingly, almost none of that draft made the final film.
- Sam Worthington, Colin Farrell, Chris Rock, Martin Lawrence, Justin Timberlake, James Franco, Seth Rogen, and Bradley Cooper were all considered for the lead roles.
Trivia / This Means War!