“Nobody wanted to do it,” Van Sant reported to IndieWire after receiving overwhelming "no's" from the individuals he asked. Damon, who had worked with Van Sant on Good Will Hunting, told the director flat out: “Gus, I did a gay movie (The Talented Mr. Ripley), then a cowboy movie (All the Pretty Horses). I can't follow it up with a gay-cowboy movie!”
Christina Applegate, Legally Blonde
Reese Witherspoon played the role of her career in Legally Blonde. But, originally Christina Applegate was originally asked to play Elle Woods. Applegate didn't want to get pigeonholed as an airhead blonde, so she decided to pass on the role.