A screenwriter turned director, Don Roos made his celebrated directorial debut with the 1998 The Opposite of Sex, a black comedy that provided hilarious and politically incorrect insights on the nature of love and sex from the point of view of a teen-from-hell anti-heroine (Christina Ricci). One of the year's most acclaimed films, Roos described it as "a post-AIDS kind of tale from the late '50s when there was the pill until AIDS there was a feeling that sex was careless and free and inconsequential and this movie has a different point of view."
Born in New York on April 14, 1955, Roos first became involved with screenwriting while an undergraduate at the University of Notre Dame, where he took a screenwriting course. Following graduation, he moved to Hollywood in 1978 and spent the next eight years writing and producing for television. During a sabbatical he wrote the screenplay for Love Field, which was made into a 1991 film starring Michelle Pfeiffer in an Oscar-nominated performance as a housewife traveling from Dallas to John F. Kennedy's funeral.
After scripting the Barbet Schroeder thriller Single White Female (1992), the women-on-the-road movie Boys on the Side (1995) (which he also executive produced), starring Drew Barrymore, Mary-Louise Parker, and Whoopi Goldberg, and the 1996 remake of Diabolique, Roos turned to directing. The shift, he was later quoted as saying, came out of the "sheer frustration of seeing [my] material handled by other people."
Following the success of The Opposite of Sex, which premiered to rave reviews at the 1998 Sundance Festival and acted as a critical breakthrough for both Roos (who earned an Independent Spirit Award for Best First Feature) and star Christina Ricci, Roos began working on his next project, Bounce. A romantic comedy-drama that starred Ben Affleck as a man who falls for a woman (Gwyneth Paltrow) whose husband's death he indirectly caused, it was released in 2000. That same year, Roos co-wrote Bless the Child, a thriller starring Kim Basinger, Rufus Sewell, and Sex co-conspirator Ricci.