Lauren Ambrose changed her mind about playing the role of the daughter whose obsession with dance and dieting almost kills her. Keri Russell soon took on the role. Russell had studied classical dance when she was younger. She said she just needed some catch-up classes.

Kevin Costner gained 20 pounds for his role.

Although Erika Christensen is six years younger than Keri Russell, she plays a sister older than Russell, and Alicia Witt, who is only one year older than Russell, plays the eldest.

Mike Binder wrote the script specifically to give Joan Allen a juicy starring role.

Mike Binder approached singer-turned-actress Mandy Moore to play Lavender "Popeye" but she backed out because she wanted to do publicity for an upcoming album.

The first song the band at the wedding sings is "Try a Little Tenderness," opening with the line "Oh, she may be weary Young girls they do get weary.." This is the same line the Costner's Crash Davis gets in a fight over in Bull Durham. Costner plays a minor league catcher in "Bull Durham" while playing a retired baseball player in this film, "Upside of Anger".

Writer/director Mike Binder said that Kevin Costner's character is an amalgamation of Detroit Tigers baseball players Denny McLain (from whom the character gets his first name) and Kirk Gibson.