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THE TO DO LIST

Attach a Wicked Funny Cast
On the heels of their success in Austin, Carey and The To Do List producer Jennifer Todd set out to attach a cast to the script.

Again, Carey turned to Plaza and Hader for help. "Aubrey, Bill and I got together and picked out our favorite actors, most of whom were our friends, and asked them to do the movie. The ensemble really is the strength of the movie," Carey notes.

Scott Porter plays Rusty, the object of Brandy's circuitous affection. Plaza had worked with him previously on Ten Year, co-starring Channing Tatum and Justin Long. When Plaza saw Porter sing karaoke while out with the cast and crew of Ten Year, she knew he was right for the role. "He's hot. He can sing. He's so perfect as Rusty," Plaza muses.

Carey, a die-hard "Friday Night Lights" fan, welcomed the referral. "He will always be Jason Street from 'Friday Night Lights,'" Carey says.

"He is a triple threat because he can sing, he can dance, and he can beatbox," Carey notes. "I didn't get him beatboxing in the movie but he did it a lot on set, which was awesome."

Porter embraced the universality of Brandy's path to adulthood: "This awkward phase of life -- sexual experiences, graduating high school, going to college, finding yourself -- it's a growing pain everyone goes through. The film is raunchy in parts, but it's about finding yourself."

Connie Britton, Porter's co-star from "Friday Night Lights," plays Brandy's mother, Mrs. Klark. Britton first read the script when Carey invited her to take part in the reading at the Austin Film Festival. Britton was unavailable at the time, but happy when the screenplay found its way into her hands again. "I loved it. I thought it was funny, and the character was great. I thought it was unique and hilarious. I have always loved comedy, and to see comedy from the female perspective is really unusual. I was thrilled when she came back to me a year later and asked me to do it," Britton says.

Mrs. Klark is one of many people Brandy reaches out to for advice. Britton explains her character's very unique stance on sexuality: "My character is different from a typical movie parent because she is cheering her daughter on in terms of her sexual exploits. My character is a nurse, so she is very much about sex education and safe sex, but also about a girl being acquainted with her own sexuality."

Clark Gregg, who plays Judge Klark (Brandy's father), was friends with Britton prior to filming. "Clark Gregg I've known for years, and I love and adore him. I'm thrilled he gets to be my hilarious, stodgy husband," Britton says.

Like Britton, Gregg loved everything that makes The To Do List so irreverent. "It's a classic sexual coming of age story, but it is set in the '90s. It's hilarious that that is already nostalgia. It is from the girl's point of view, with a woman writer-director. It felt like a specific, unusual, feminist, raunchy tone. That I liked."

While Mrs. Klark is perhaps too permissive, Judge Klark is helpless in his futile attempts to control Brandy's burgeoning sexuality. Gregg explains: "Judge Klark does not want to know. He knows his daughter will become sexually active, but he wants to put it off as much as possible. He vetoes the concept of her mom handling it because he feels that the permissive, go-for-it sex talk she gave to their older daughter led to them having a very tarty daughter. He feels like he wants to intervene, but that leaves him stuck in the position of actually having to talk about stuff that makes his skin crawl."

Carey notes that the unusual complexities of the Klark household contribute to Brandy's frankness: "Brandy has a very liberal mom and a very conservative father, and she's the product of that. She does have an unusual relationship where she's very open and forthright with her parents. In a weird way that is probably what you want as a parent because you have a very trustworthy daughter, but as she's going through this adventure she's telling them about it, which the dad wants nothing to do with but the mom's more than happy to talk about," Carey explains.

Rachel Bilson joined Gregg and Britton as Brandy's older sister Amber, who acts as "the sexpert, so to speak, so I get the ball rolling for her," Bilson jokes. Bilson's agents brought the script to her with a few disclaimers about the frank depiction of sexuality. "When I first read the script, my agent said, 'I don't know how you're going to feel about this. It's a little raunchy,'" Bilson recalls. "I remember reading it and thinking, 'Of course I want to do it!' Thank God I read it!"

"I love the rivalry between my character and Aubrey's character," Bilson adds. "The older sister gets all the crap and the younger sister gets away with everything."

"She was so perfect for the part," Carey says of Bilson. "She's so funny and witty, and so quick. She's great on the first take and she improvised a lot of her lines. She brought so much more to the character of Amber."

Brandy's relationship with her sister grows and changes as Brandy matures. "I think Brandy maybe looks down a little bit on her sister. Brandy is the mathlete. She's the one who got the perfect score on the SATs. Before this, she might have talked down to her sister. Suddenly, when she needs to know about sex, her sister is a wealth of knowledge for her," Carey says.

Johnny Simmons, Plaza's co-star from Scott Pilgrim vs. The World, took on the role of Cameron. "I saw him in Scott Pilgrim and was such a fan," Carey says. "He plays the character of Cameron so sweetly. He's the nice guy that the girl doesn't want to date."

Carey further explains Cameron's very specific, unusual quandary: "Brandy is perhaps more stereotypically male in that she's a little bit more clinical and it's more about checking things off a list and getting an accomplishment, whereas Cameron is very much the romantic and in love with her and wants his first time to be with her. It definitely is a role reversal."

Alia Shawkat and Sarah Steele play Fiona and Wendy, Brandy's best friends. Carey was impressed by Steele's acclaimed performance in Nicole Holofcener's Please Give. Plaza suggested Shawkat for the role of Fiona. "Alia Shawkat is one of my very, very dear friends," Plaza says. "Fiona is an old soul and wise beyond her years, and that's how Alia is in real life. She has all the answers."

Fiona may be wise, but Wendy often has the last word. Carey explains: "I love how their characters play over each other. They sometimes talk over each other and Wendy tends to win. She gets there a little bit later, so you get to hear the crazy things that come out of her mouth."

Fiona and Wendy are the best friends every girl can relate to having. In fact, Carey had a similar affinity for Beaches, the Bette Midler/Barbara Hershey film referenced in The To Do List. "When Beaches came out, my friend called me crying because her mom and her aunt had just seen the movie and she said that we needed to see it and that if I saw it with anyone else but her, then we wouldn't be friends anymore," Carey remembers.

Donald Glover, a fellow UCB alum and friend of Carey and Plaza, spent his days off from "Community" to play Adam. Two of Hader's previous cast mates rounded out the ensemble: Christopher Mintz-Plasse, Hader's co-star from Superbad, joined as Duffy, and fellow "SNL" alum Andy Samberg plays Van. "I definitely wanted an Eddie Vedder-inspired wannabe grunge rocker and I think he nailed that," Carey says of Samberg.

At least one cast member won't get to see how his performance turned out: "Modern Family's" Nolan Gould, who also appeared in Friends With Benefits. Gould wasn't allowed to read the script. "This is the second movie I've worked on that I won't be allowed to see until I'm a lot older," Gould says.

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