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One of the delights of Michelle Morgan's screenplay is the assortment of oddballs and eccentrics she has assembled to represent the two sides of Imogene's life. "The screenplay is very character-driven, which is something I'm always drawn to," says Wiig. "All the characters are so interesting. You don't see those kinds of personalities that often and it makes for a really interesting story that is funny, without trying to be."

Wiig brings her own accessibility and empathy to the character of Imogene, who could, her creator admits, have been a bit unsympathetic as she reverts to childish ways when returned to her childhood environment. "Kristen is relatable no matter what she's doing," says Morgan. "She's so warm and sincere. I can't see anyone else playing Imogene. The character is so flawed that, in someone else's hands, there are moments when you wouldn't have liked Imogene. Kristen inspires such compassion that it works. I feel extremely lucky that someone as cool and talented as her would even agree to say the words I've written."

The actress always saw more in the character than just an awkward, funny girl with wacky mother issues. "As skilled as she is at broad comedy, Kristen is also really good at finding the truth at the heart of a character," says Pulcini. "It makes the funny stuff funnier if it's couched in something real."

Playing Imogene also takes Wiig in a new direction professionally, says Rattray, one that will reveal the actual depth of her talent. "Kristen Wiig has proven herself to be the most talented comedic actress of her generation," says Rattray. "And she's a fabulous dramatic actress to boot. I think she was interested in this role because it had more dramatic content than what she's done in the past. She liked where it stood in the combination of dramatic versus comedic moments."

Wiig approached the project with a work ethic that set the bar high for her co-workers. She was never content to be a producer in name only. "She's incredibly hard working," Rattray says. "She gave her all at all times and was a very active producer for the film. She cared about every single issue, including casting, and she was generous with her creative opinions."

Wiig says her own experiences and insecurities as a writer gave her a window into Imogene's head. "Imogene had the opportunity to write a play, but she put it off because she was scared it wouldn't be good enough. That's something a lot of writers feel. For me, sitting down to write means being vulnerable. You have to show it to someone else and you are always wondering if it's going to be good. I have that fear, so I relate to her procrastination. It's something you have to fight through."

At the beginning of the movie, Imogene is leading the life that she thought she always wanted, but she manages to lose her European beau, society girlfriends and literary cachet in short order. "She's always believed that happiness depends on social status and having money," Wiig says. "After the breakup with her boyfriend, she loses all of that. She goes into a downward spiral, but she discovers what's really important through the family she tried to leave behind."

Her long-held dreams of artistic success and social status complicate Imogene's real-life relationships, explains Morgan. "Growing up she always wished she was part of another family -- people who spoke in a different way and valued different things. When she became an adult she could choose her friends and she chose the people she fantasized about as a child. Reunited with her family, she begrudgingly starts to realize that they have a lot more heart than anyone else in her life. They're good people and she's a lot more like them than she wants to admit. When she makes peace with that, her life goes in a much more positive direction."

Four time Oscar nominee Annette Bening plays Zelda, Imogene's free-spirited mother, a gambling-addicted, unapologetic Jersey girl who long ago stopped trying to make sense of her daughter's lofty ambitions. The character is a hilarious departure for the actress, better known for portraying elegant and sophisticated women.

"For Annette, this is going completely against type," says Rattray. "She wanted to do something different, but not a caricature or a 'Jersey Shore' type performance. It took a lot of heart and she committed totally. Annette was talking with a Jersey accent even when she was off camera."

It's also a rare opportunity for Bening to show off her considerable comic chops. "She's one of the great actors of our time and she doesn't do comedy often enough," says Pulcini. "Annette wanted to get this right, so she spent time in Ocean City, doing research and sampling the pizza. Like Kristen, she wanted to make her character real, which is always funnier."

Wiig can't say enough positive things about working with Bening. "I'll talk about Annette Bening as long as you want," she says. "I was such a huge fan of hers before we did this movie and now I'm even more so. Besides being an incredible talent, she's just a beautiful person. Being able to do scenes with her is one of the highlights of my career. I feel really honored that we got to work together."

Rattray, who worked with Bening on The Kids Are All Right, is just as enthusiastic. "She is a class act and such a talent," the producer says. "Whenever she walks on the set, she makes it a happier place. Annette was our first choice for the role, and luckily for us, she is a huge fan of Kristen, so she responded very quickly."

Over the course of the film, Imogene's relationship with Zelda changes drastically, as the daughter discovers information that forces her to view her mother's foibles through new eyes. "In the beginning, we find out they haven't seen each in something like eight years," says Wiig. "When they are reunited, they're strangers who have to find each other again and the way it happens is quite beautiful. Imogene thinks of herself as very different from her mother and has a lot of resentments she has never dealt with. Now, as an adult, she's forced to look more closely, and they end up coming together on the other side of it."

Not that Zelda will ever win the Mother of the Year award. "When we first meet Imogene and Zelda, their relationship can only be called catastrophic," says Styler. "There's been a lot of water under the bridge, due in no small part to Annette Bening's character's predilection for gambling, her OCD and the withholding of important information about Imogene's father.

"There's a lot we shouldn't like about Zelda," Styler continues. "But Annette brings such warmth and humanity to the role. We see from the mother's point of view that she had to juggle a lot of balls. She did the best she could with what she'd been given. I don't know one family that can't claim some dysfunctionality, but there's an awful lot of love here as well."

A major point of conflict between Imogene and her mother is Zelda's live-in boyfriend, the improbably named George Bousche. Zelda's latest paramour is a self-professed covert agent with an unlikely story for every occasion and a habit of disappearing without explanation.

Screenwriter Morgan recalls that during the period she lived with her mother as a young adult, her mother had a new boyfriend who spent a lot of time in their house. "He told outlandish stories that I couldn't believe were true, which is how Zelda's boyfriend, the Bousche, came to be."

Matt Dillon plays the Bousche with the offhand charm and goofy conviction that will remind audiences what a skilled comic actor he is. "This role is reminiscent of the comedies he did earlier in his career, like There's Something About Mary," says Rattray. "It was really fun to work with him on that role. He has a way of saying outrageously unintelligent things with such sincerity and intensity that he steals the scene."

"We've been huge fans of Matt's since his first films," says Berman. "He is often underappreciated as a comic actor, so this was a fun opportunity to show how much he can do. He and Annette have great chemistry so they are even funnier when they're together."

Adds Styler: "He's just terrific. I can't even think about his performance without laughing."

Despite the hilarity of his performance, Dillon took the espionage angle of character seriously, say the directors. "Matt did a lot of homework about the CIA," Berman notes. "He really immersed himself in the role, which was a lot of fun. He had strong ideas about what his character should wear -- and the nunchucks were his idea."

The actor often stayed in character between takes and kept cast and crew in stitches with wild descriptions of his crazy adventures in espionage. "Matt is so funny," says Wiig. "He had everyone laughing on set constantly. I'm really excited for people to see him in this role."

Returning to the familial home is one rude shock after another for Imogene. Not only has Zelda stashed most of her remaining belongings in a remote corner of a dank cellar, she has also rented Imogene's room out to Lee, played by Darren Criss. Initially put off by the interloper, Imogene soon falls for the undeniably handsome young boarder.

Because Lee has a job in an Atlantic City revue impersonating pop stars, the role required someone with singing and dancing talent, as well as great looks. Criss, who stars in the hit television series, "Glee," fit the bill.

"I'd never watched 'Glee' but I did a YouTube search and found an interview where he sang the answers with his guitar," says Pulcini. "He seemed like he would be perfect for the role and a great foil for Kristen. When he auditioned, we knew he was the guy."

"Darren was the perfect person for the role," offers Wiig. "He had to sing, be charming, and he's just so sweet and really, really funny."

The film is a career benchmark for Criss: his first big-screen role. "We auditioned a bunch of young guys to find a complement to Kristen," says Rattray. "We were looking for someone young and fresh, who is a great singer-dancer and an unlikely romantic match who somehow suited her. Darren is very dynamic. We were unanimous that he was the right guy for it and it's the perfect first film role for him."

Because of his commitment to "Glee," Criss commuted between Los Angeles and the East Coast film set. "It seemed like he would no sooner arrive than he would be back on the plane," says Styler. "He's somewhat of a hero as a cast member and a delightful human being, besides being so talented. I know I'll be watching Darren's work for a long time to come."

The actor found a lot of parallels between himself and his character, right down to their taste in automobiles. "As we were shooting he would say, I'm so much like this guy!" says Berman. "At one point, he said, 'I used to have the car that Lee drives!' We were so pleased to work with someone with that kind of enthusiasm and drive. We threw him in with major movie stars and he kept up with everybody."

In addition to the film's major roles, Girl Most Likely is loaded with hilarious supporting performances, including veteran actor and director Bob Balaban as a mysterious figure from Imogene's distant past, and Christopher Fitzgerald, a well-known stage actor whose credits include "Wicked" on Broadway, as her crustacean-obsessed brother. "I love Christopher Fitzgerald's portrayal," says Styler. "As extreme as the character is, I found him the most truthful of all the family members."

Wiig agrees with that assessment, adding that she can't wait for audiences to see Fitzgerald in the film, and calling him, "one of the most brilliant actors I've worked with and one of the funniest people I know."

Writer Michelle Morgan returns to acting in the film as Georgina, one of Imogene's circle of well-heeled frenemies. An East Side "It Girl," Georgina's social status relies on her relationship with queen bee Dara, who has declared Imogene persona non grata.

"Georgina is one of Dara's minions," she says. "She worships her and agrees with everything Dara says. If Imogene is out of favor with Dara, that's how it is with the whole group."

Morgan was delighted to appear in the film, although she says watching the film come together each day was the real thrill. "I was on set for most of the shoot, but, as the writer, you kind of have to stand back," she notes. "They gave me a chair to sit in and I got to watch it come to life."

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