"Three to Tango" was inspired by screenwriter Rodney Vaccaro's own bizarre romantic experience. While working as creative director of a large advertising agency, Vaccaro met Joan, a woman who was then living with his boss. A series of what he describes as "sexual errors" led to Vaccaro eventually marrying Joan and in turn, provided the basis for the original screenplay of "Three to Tango."

For producer Bettina Sofia Viviano, "Three to Tango"'s long trek from page to screen was also a labor of love. Viviano optioned the script in 1990, and for the next eight years, stuck with the script through a succession of deals and near-deals that, while not atypical in Hollywood, reads somewhat like an adventure road movie. Along the way, Kari Selig (later co-producer) and Larry Abramson (executive producer) joined the team, which eventually allied with Outlaw.

Viviano reflects, "No matter who came aboard and who drifted away from the project, I kept championing the script. I loved it and believed in it from the first and my enthusiasm for it never waned. I knew it was going to make one helluva movie."

Producer Jeffrey Silver (who, with his partner in Outlaw Productions, Bobby Newmyer, had recently completed the Meg Ryan-Matthew Broderick starrer "Addicted to Love") was struck by the script's offbeat sense of reality set within the confines of a traditional romantic comedy.

"It's an exciting and very entertaining story that looks at life through a different lens," explains Silver. "The idea of a gender-bending comedy is interesting to me, not because of the gender issue, but because it allows you to examine life from another perspective. Oscar's life is turned upside-down and, through him, we all have the chance to see a different view of the world."

Newmyer adds: "The script for 'Three to Tango' had a totally unique and original twist that kept the two lead characters apart from one another. In the context of this movie, the worst thing that can happen, does-Oscar finally falls in love but cannot openly express that love because it would jeopardize everything he's built. He finds himself living in this 'house of cards' that he desperately needs to keep standing, while at the same time, he really just wants to blow the whole thing down."

For a project this distinctly off-kilter, Silver and Newmyer wanted a director who could not only bring a sense of humor to the project, but one who could also relate to the off-beat sensibility of the story. The producers had seen Damon Santostefano's work-his CableACE Award-winning Nickelodeon series "The Adventures of Pete and Pete," as well as his inventive MTV pilot, "Love Dies and Then You Do," the series "Clueless" and Comedy Central's "Bob and Sully."

"Damon's work is original and cinematic" explains Silver. "His approach is fresh and, at times, irreverent and wickedly funny, but he also brings a firm directorial hand and an excellent sense of timing. We felt that he could give us something that's fresh, funny and highly original."

On first reading, Santostefano was hooked: "It's hilarious and yet has a lot of layers-social commentary and physical comedy along with some very heartfelt moments between characters who are learning how to fall in love. The writers created a smart comic tone-grounded characters in outrageous situations that managed to be emotionally believable."

With Santostefano in place, the team devoted their attentions to assembling a cast that could maintain the realistic human qualities of the characters while making the most of every laugh in the script.

For the central character of Oscar, the lovelorn architect trapped into living a lie, filmmakers sought Matthew Perry. "We started courting Matthew's manager and agent as soon as we got involved with this script, when it was only a twinkle in our eyes," laughs Newmyer. "That was a full year before he was actually cast in the picture. To us he was (and is) the only guy to play this role."

"No other actor has Matthew's ability to be ironic and completely vulnerable at the same time," explains Santostefano. "He also has a great range as a dramatic actor."

Perry, perhaps best known as television's Chandler Bing on "Friends," recognized in "Three To Tango" a chance to explore new territory as an actor. "I wait for a good script to come along, one with a part that looks like it would be fun to play. I was attracted to this film because of the very interesting dynamic of the character. He's had intimacy issues with women for pretty much his whole life. Now, by having to pretend that he's gay it's finally safe for him to get to really know a woman and ultimately to truly fall in love with her."

Filmmakers approached Neve Campbell to play the sexy, spirited Amy, the center of "Tango's" ultimate love triangle. "Neve has huge sex appeal," explains Silver, "and a star quality that transcends her age. There is something about her that is immediately lovable and that is essential for Amy. Her character is simultaneously falling for one man whom she thinks is gay, and involved with another, married man. It's her challenge to stay real, and she does that wonderfully."

Santostefano made the choice unanimous: "Neve added a depth to Amy's character that is refreshing and unexpected. At the same time, she is a truly funny lady, and brought a really eccentric sense of humor to the part."

Campbell, who made such a strong impression in the acclaimed, long-running series "Party of Five," as well as the ultra-hip thrillers "Scream," "Scream 2" and "Wild Things," was eager for a chance to lighten up and have fun on screen. "This is such a departure from the roles I've been playing recently; all of them have been fairly heavy. I love those intense characters but I also wanted to portray a character that really has fun for a change. Comedy is very different from the drama that I've been associated with so long, and I really welcomed the chance to challenge myself and to lighten up in the process. I get to be funny, I get to laugh and I get to fall in love. Nobody dies in this film, no one is terrorized. And, for the first time in my career, I am not playing an orphan."

With Perry and Campbell set as Oscar and Amy, discussion turned to filling the role of the powerful industrialist, Charles Newman. Newmyer recalls, "Of the four principal roles, the most challenging part to cast was Charles. The man is a multi-millionaire Chicago industrialist and it is hard to realistically imagine this man could be that successful at an age any younger than say late thirties or even his forties. Dylan McDermott is the only guy who is really so dashing and so genuinely appealing that you can immediately understand the relationship with Neve's character. At the same time, he just exudes a cool sense of power and control that really makes him the epitome of the modern power broker."

Silver breaks in with a laugh: "'Liquid sex!' That's how People magazine described Dylan McDermott and they must be right. The man is incredibly smooth. He is totally convincing as this powerful, ultimate tycoon, while remaining genuinely charming and funny. Dylan has that combination of youthfulness and 'James Bondian' savoir-faire."

Making up the 'fourth wheel' of the film's love triangle is Oscar's business partner, Peter Steinberg-a combination of comic foil, "straight" man to Perry's Oscar (Peter is openly gay) and the cool voice of reason. Oliver Platt, one of the busiest actors in Hollywood, was approached with the challenge of breathing life into this character. "Oliver rides a fine line, playing a comic role without ever falling into caricature," comments Silver. "He keeps it off-center and, at the same time, completely grounded. Oliver has the remarkable skill of always bringing his work right down to a real character."

Santostefano concurs, "Oliver is just an amazing actor. He brought a wealth of ideas to the character of a workaholic architect and played the role with intelligence, comedy and pathos."

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