Megan Fox was cast in her role before Transformers (2007) was released. Director Robert B. Weide had hoped he would have been the one credited with uncovering this new talent and so after Transformers (2007) was a big hit and Fox quickly becoming an international sex symbol, he remarked he was disappointed, not for her but for the fact he wasn't the one who first brought her to the cinematic stage.
The film makes several references to the Coen Brothers' film The Big Lebowski (1998). Sydney accidentally calls Mrs. Kowalski "Mrs. Lebowski". Also, Maddox is identified by drinking White Russians, the drink of choice for The Dude, played by Jeff Bridges in "The Big Lebowski". Also, Simon Pegg called Jeff Bridges 'dude' at one point, and Jeff Bridges claimed, "I'm not 'the Dude'.".
More Lewbowski references: The character played by Kirsten Dunst comes from Port Huron, Michigan. In The Big Lebowski (1998), the Dude is the co-author of the radical Port Huron Statement from the 1960s.
During the montage of Sidney's name appearing on guest lists to parties and exclusive events one of the names about Sidney's on a list is Oscar Wright - younger brother of writer/director Edgar Wright, who is a frequent collaborator of Simon Pegg.
The movie's title (and concept/execution, to some degree) parodies the bestselling self-help book "How To Win Friends and Influence People", written by famous author and lecturer Dale Carnegie. Carnegie's advice strives to paint a veritable "roadmap to success" in personal and business relations. The book remains popular and is frequently employed as a resource in corporate training programs and other similar applications whose aim is to strengthen the interpersonal and problem-solving skills of their audiences.