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Casting The Film
According to the producers, the key to the whole film was to cast someone who can portray Sidney Young in a sympathetic light. Producer Stephen Woolley says: "The character of Sidney Young is fairly close to the character that Toby [Young] creates in his own book with one slight difference: I think that Sidney is a hell of a lot more sympathetic than Toby's character, and that doesn't come through necessarily only in the writing, that comes through Simon Pegg. Simon is generally somebody that, no matter how hard or tough or bad they seem, you always know that it's Simon Pegg and in the end he's going to make you smile. You instantly love him: he's an instantly lovable guy.” Toby Young jokingly adds: "He is immensely likeable, you can't dislike Simon and given how appalling the character he's playing is, I mean me, being so likeable is a hugely important quality.” Director Robert Weide explains: "Simon just has that way about him that he can get away with anything; he can say really obnoxious things, act like a jerk and be very inappropriate, yet he is just so likeable at the core that I think the audience's sympathies will stay with him and they will root for him. Simon is able to walk that line between just being really uproariously funny and being a very sympathetic character that I think you care about.” 

Robert Weide had become a fan of Simon Pegg's work and thought that he would be perfect for the role due to his proven comedy track record with Shaun of the Dead and Hot Fuzz. Robert comments: "Simon needs very little directing as his first instincts are always so good. I literally cannot imagine having done this film without Simon now, I don't know who else could have played him, I don't know who could have ridden that line between being so obnoxious and so sympathetic and so funny.”

Simon Pegg was first drawn to the project because of the screenplay, he says: "I read the script and I really liked it. I think Peter [Straughan] is a really good writer, it is funny and it just had what I think as an actor you look for in a script which is a challenging character and an interesting situation. When you read the book you think how could this possibly be turned into a film? But he's taken the spirit of it and the heart of it and put it on the screen, the page, which is a really clever thing to do. It's a funny comedy, a lot of which is based on truth.” 

Director Robert Weide's attachment to the project was also a big draw because of his comedy background directing Curb Your Enthusiasm. Simon Pegg explains: "When you're doing a comedy it's really important that the person behind the lens understands the dynamics of comedy. They have to be, the best comedies are shot by funny people and Bob's a very funny guy.”

Kirsten Dunst plays Alison Olsen, Sidney Young's colleague and eventual love interest. Stephen Woolley and Robert Weide had previously worked with Kirsten Dunst on Interview with a Vampire and Mother Night respectively. Stephen has watched her career since and thought of her for the role because of Bring it On which "is really funny and Kirsten is terrific in it. It is this film that made me think, she really knows humour,” states Stephen. 

Drawn to the project for a number of reasons, Kirsten says: "20 pages into the script you can usually tell whether it's good or not, and I was laughing. And when I had heard that Simon was attached, I'd seen Shaun of the Dead and was a big fan of his and I really wanted to work with him. It was nice to have the comfort of knowing Bob [Robert Weide] and having an environment where everyone just really wants to have good time together and is open. I felt very collaborative from the very beginning with Bob, we all respect each other a lot.” She adds: "I'm very instinctual about the things that I do and with the people that are surrounding the project. So meeting and knowing Bob and rea

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