“Right off the bat, Donna, Susan and Gina all agreed that Mark was the one,” says Winick, “which pleased me enormously because I thought they’d be going after a more typical Hollywood-type leading man that we usually see in this kind of romantic comedy. Mark is a serious actor with a huge independent film background and he brought a completely different dimension to the part.”
For Arnold the choice of Ruffalo was a no-brainer. “In addition to being an amazing actor, you get the sense from Mark that he can genuinely portray Matt’s earnestness and devotion. He’s the kind of guy you can see Jenna falling in love with.”
Ruffalo’s style also complemented Garner’s in a way that Matthews felt would give the story a solid grounding in reality. “Mark has a sort of dry wit that made his scenes with Jennifer very real. Every choice he made was a completely honest one.”
Ruffalo enjoyed the opportunity to play with the character of Matt Flamhaff since, as he puts it, “I usually end up playing more intense characters. But I had a lot of fun with Matt. He’s a pretty straightforward guy, but he also has this wonderfully goofy quality as well.”
In Matt, Ruffalo saw an incomplete human being who not only helps Jenna come to better understand who she is, but discovers something about himself as well. “In a lot of ways Matt is shut down. He’s given up on the idea of romantic love because he was burnt so badly by Jenna when he was younger. She kind of re-ignites his passion.”
The chance to play opposite Ruffalo was exciting for Garner, she admits, since she was a not-so-secret fan. “Mark is delicious. I don’t know anyone who saw You Can Count on Me who didn’t fall head over heels for him,” she says. “If, at that time, you would have told me that I would be working with him a few years later, I wouldn’t have believed you. It would have been a total dream come true.”
Jenna’s nemesis in the film is the very cool and popular Lucy (a.k.a. Tom Tom), who is portrayed by Judy Greer (Adaptation). Winick labels Greer “unbelievable, a comic genius. She was our secret weapon.”
For Greer the role is more of a stretch than one would imagine. “It’s weird that I got to play the girl who was the most popular in school because that was so not the case with me. Also, Lucy can be pretty mean. I make Jenna do my homework for me. I try to control her and use her as a stepping stone to get what I want.”
British actor Andy Serkis (The Lord of the Rings trilogy) earned the role of Richard, Jenna’s flamboyant boss at the troubled, high fashion magazine Poise, who is at first frustrated and then charmed by Jenna’s antics. “Richard has always thought Jenna was a bit eccentric. But they have always been creatively in tune until recently. Now she seems a bit off and he is thrown by her,” says Serkis.
While he plays a very colorful character, Serkis was careful to keep his actions in the proper perspective. “I always wanted to be certain that it was the situation that was funny, not the character.”
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