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How to Lose Friends & Alienate People (2008) Poster

Trivia

The book that the staffer was reading (Chris O'Dowd) in the scene where Clayton Harding calls is in fact the the novel "How to Lose Friends and Alienate People", the book on which the film was based.
Jump to: Cameo (1)
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.
Toby Young, the man around whom the film is based, was banned from the set as he was reportedly annoying actors and interrupting Robert B. Weide as he tried to direct scenes.
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'.".
The scene where Sidney asks an actor "Are you gay?" is based on Toby Young doing the same to Nathan Lane regarding his role in The Birdcage (1996).
The scene where Sidney leaves Elizabeth Maddox alone in the hallway after she tripped and fell is based on a similar incident involving Anna Wintour and a Vanity Fair intern.
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.
In the scene where Sidney first meets Sophie Maes, the man standing directly next to her on the right side of the screen is Brian Austin Green, who was at the time of filming, Megan Fox's fiancé.
Janette Scott's first cinematic appearance in 41 years.
Simon Pegg was approached to play the role of Young back in 2004 for a stage version, but this conflicted with shooting on Shaun of the Dead (2004)
Clayton Harding is a fictionalization of Graydon Carter.
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.
In the beginning of the film, Simon Pegg is trying to catch Thandie Newton's attention. Thandie Newton was the love of Pegg's life in the movie Run, Fatboy, Run (2007).
The relationship between Sidney and Alison is not in Toby Young's book, it is instead based on The Apartment (1960).
Part of the films marketing involves a spoof trailer for an erotic Mother Teresa biopic, in which Megan Fox's character Sophie Maes appears as the young and passionate Teresa.
Sidney Young's library card is from Gloucester. Simon Pegg was born in Gloucester.
The book Alison Olsen is reading in the break room when Sidney sits down with her is "Relative Stranger: Piecing Together a Life Plagued by Madness" by Mary Loudon.

Cameo 

Stephen Woolley:  Producer has a cameo as one of the members of the queue behind Sidney at the airport. He is the man with long hair wearing dark glasses.
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