For director Daniel Taplitz, Breakin’ All The Rules evolved from a character study of one of his best friends. “I had a friend who was quite a ladies’ man,” he remembers. “And he had this thing where he would go out with women but was so paranoid about the relationship that he would often break up with them if he suspected they were going to break up with him first. He had all these rules for how he could call, when he could call, when he could break up – and I always thought it was fascinating that he had codified it to some degree.”

Coincidentally, Taplitz came across some employee termination research, which outlined the best possible ways to fire employees without getting into a dangerous situation. “The research is extensive,” he continues. “There are many books written on the subject in great detail – what to say, when to say it, where to say it – it’s a real science. I started thinking about my friend and his rules, and how people are so bad at breaking up with each other. So I combined the ideas of ‘how to fire someone’ with ‘how to break up’ and came up with the premise for the script. It’s basically a ‘how to fire’ a boyfriend or girlfriend, using the employee techniques of how to fire an employee without making them go postal.” And so Breakin’ All The Rules was born.

Jamie Foxx was Taplitz’s first choice for the role of Quincy. “Jamie has so many instincts and he’s sort of a free-flowing brain,” he says of the actor, “but I’ve never seen him do a romantic part and I always thought that he would be great at that.”

Foxx read the script and quickly responded. He not only liked it, but the whole idea of a breakup handbook spoke to him. “I read the script and it got me thinking,” says Foxx. “It’s the hardest thing in the world – when you really love a person, but you know that this is as far as it’s gonna go. So you start leaving all these signs like not answering the phone or not showing up – that’s such a male way of doing things, but that’s how we handle it. A book telling us how to handle a breakup is just what men need.”

Foxx’s interest excited producer Lisa Tornell because she thought it might be difficult to find the actor who could believably play Quincy with a comedic flair yet also have that romantic lead magnetism. “A lot of times you get one or the other,” she says of her search for the perfect fit. “But Jamie is so naturally funny with an amazing comic ability, and he hasn’t had a chance to play the romantic lead yet. His performance in Ali was so committed and so great that we thought ‘if he can do that that believably, and he can be funny that believably, he can probably do anything.’ And in the end, he does – he’s funny, holds the screen and has real romantic guy presence.”

The next role to be cast was Evan, the real hound of the pair – the one who just can’t commit. Or as Jamie describes his co-star character, “the young black, smooth brother who wants to be a player but does it all wrong.” Morris Chestnut quickly won the role. “Morris seemed like the right person for the role and hadn’t been used in that way, which I found refreshing,” says Taplitz. “He has such natural sympathy to him – you look at him and want to take him home to meet your parents! So putting him in the stronger, more arrogant role and coupling that with his natural appeal would allow the audience to connect with him.”

For Chestnut, he was attracted to the free-spiritedness of his character of Evan. He liked the fact that he says what’s on his mind, lives for the moment and is just having fun; yet his professional life remains very structured. “I know a lot of Evans,” says Chestnut of his character. “One of my close friends is an Evan. He can’t stay with a woman more than two weeks. This is pretty common among men because a lot of them get bored easily with women for whatever reason. Then it’s hard to break up with them because they think they’re in this serious relationship, and then suddenly, they’re being let go.” Working with longtime friend Jamie Foxx was another motivator for Chestnut since they have a close off-screen rapport. It was a great opportunity to bring that to the screen. “I really looked forward to working with Jamie,” he says. “I like to just sit and watch him work and see the process that he goes through. I have a lot of respect for him. He’s a true professional.”

The role of Nicky seemed tailor-made for Gabrielle Union. “Gabrielle is gorgeous and has a center to her, which is a perfect foil to Jamie,” says Taplitz. “Off screen, you can see him actually sitting up straighter and having better manners when he’s in the same room with her!” Says Union, “I was like Nicky about fifteen years ago, but all it took was getting broken up with one time and it never happened again. I vowed I would never again be the victim.”

Union feels that many women go through the ‘if I just change something about myself or about my life, I’m gonna keep this man,’ and that is exactly what Nicky ends up doing – cutting her hair to shock Evan. But it backfires. “Women often will make excuses for men,” says the actress. “They become obsessed with keeping that man, no matter how badly it’s going as opposed to being alone

With the three leads in place, the film was coming together. The filmmakers next approached Peter MacNicol for the role of Phillip, the owner of a magazine publishing company that he inherited from his father. He is a weak, helpless man who is trying desperately to break up with his barracuda of a girlfriend, Rita. But no matter what he says or how he says it, his girlfriend just won’t have it. So he seeks the advice of Quincy to help him find just the right way to break up with her. “This movie is a romantic comedy but very old-fashioned in its structure, very classical and elegant,” says MacNicol. “It’s a throwback feeling to movies of another era, complete with mistaken identities and smart wit. That’s what drew me to this project. It was really the script.”

Jennifer Esposito was cast in the role of Rita Monroe. “Rita is a very aggressive woman who is going after exactly what she wants,” says Esposito. “It happens to be money and she has no apologies for that. And when she finds out that Phillip has paid someone for advice on how to break up with her because of her overbearing nature, Rita tries to intercept and creates a hilarious triangle.”

Rounding out the cast are Bianca Lawson, who plays Helen, and Jill Ritchie, who plays Amy. “Helen is fun, dramatic and over-the-top,” says Lawson of her character. “I haven’t done this kind of comedy before so I thought it’d be fun to just let loose.” For Jill Ritchie, playing the role of the best friend attracted her for many reasons. “Amy thinks that Nicky and Evan should be married and that they’re a beautiful couple, and she just lives her love story through them because she has no love life of her own. Amy is one of those people who loves love, and I related to that.”

Set against the backdrop of the magazine publishing world, Breakin’ All The Rules was shot completely on location in Los Angeles. And in the end, the cast all took away a little something about how to break up with someone. “There’s no surefire way to break up with somebody. It’s the challenge that we will have for the rest of our existence. How to stay in love and how to deal with it when you fall out of love are both things that we’ll never be able to have all the answers to, but we can offer a lot of suggestions,” replies Foxx. “No matter how you slice it, when you get cut from the team, it’s gonna hurt!”

JAMIE FOXX (Quincy Watson) stars in the FX cable movie “Redemption: The Stan Tookie Williams Story” this April with Shane Daly and Lynn Whitfield. In August, Foxx will co-star with Tom Cruise in the action-thriller Collateral directed by Michael Mann and in the fall, Unchain My Heart: The Ray Charles Story, which was directed by Taylor Hackford. He and is currently shooting Stealth for director Rob Cohen, starring Josh Lucas and Jessica Biel.