Frears cast Bening alongside John Cusack and Anjelica Huston in his classy film noir, "The Grifters" (1990), adapted from the novel by Jim Thompson. Although it was her nude scenes in the film which generated the most publicity, Bening injected considerable verve and authority into her portrayal of a tough young hustler who coolly uses her body as one of the tools of her trade--a performance intentionally modeled after Gloria Grahame's in Fritz Lang's landmark noir "The Big Heat" (1953). The role earned Bening a Best Supporting Actress Oscar nomination, propelled her into the front rank of Hollywood leading ladies and prompted references to her as the "thinking man's sex symbol." She went on to demonstrate her versatility by portraying nurturing, supportive wives in "Guilty By Suspicion" and "Regarding Henry" (both 1991) before returning to a more seductive role opposite future husband Warren Beatty in "Bugsy" (1991), surprising everyone by winning the heart of the Playboy of the Hollywood World.

After a three year hiatus to marry and start a family, Bening and Beatty again co-starred, this time in "Love Affair" (1994), the second remake of a 1939 film of the same title. They played two people engaged to others who fall in love after an accidental meeting. While many hoped to draw comparisons between the couple's real-life romance and their film characters, the pair vehemently denied any connections and the on screen results were less than stellar. Juggling motherhood and a career, Bening has made sacrifices, relinquishing the coveted Catwoman role in "Batman Returns" (1992) when the stork first flew into her life and dropping out of "Disclosure" (1994) due to her second pregnancy. She won acclaim for her deft comic turn as a lobbyist romanced by "The American President" (Michael Douglas) and as Queen Elizabeth in Ian McKellen's adaptation of Shakespeare's "Richard III" (both 1995).

After appearing in Tim Burton's "Mars Attacks!" (1996), Bening starred alongside Bruce Willis and Denzel Washington in "The Siege" (1998) and teamed with Aidan Quinn as a psychic with telepathic connections to a killer in Neil Jordan's "In Dreams" (1999). She followed with what many felt was her best work in years, playing the domineering real estate broker wife of a man undergoing a mid-life crisis in the acclaimed "American Beauty" (also 1999). For her performance, she netted a Best Actress Academy Award nomination. Bening followed with a comic turn opposite Garry Shandling in the Mike Nichols-directed comedy "What Planet Are You From?" (2000). After a lengthy hiatus from the screen, Bening—who dropped out of the Disney comedy remake "Freaky Friday" shortly after filming began—took on the role of actor/director Kevin Costner's spirited and refreshingly age-appropriate love interest Sue Barlow in the under-appreciated Western revival "Open Range" (2003).

The actress then accumulated some of the best reviews of her career when she starred as a diva stage actress caught up in a May-December romance with a young social climber only to end up plotting a delicious revenge in "Being Julia" (2004), a bravura turn that ultimately earned her a Golden Globe award for Best Performance by an Actress in a Motion Picture - Musical or Comedy. Hot off the heels of her Golden Globe win, Bening grabbed an Oscar nomination for Best Actress in a Leading Role and was considered a heavy favorite going into the awards. She received continued critical adulation for her performance in “Running with Scissors” (2006), an adaptation of Augusten Burrough’s best-selling memoir about his growing up in the home of his mother’s therapist (Brian Cox). Bening played Burrough’s delusional mother, an unpublished poet dealing with a messy divorce with her son’s alcoholic father (Alec Baldwin), which earned the actress a Golden Globe Award nomination for Best Performance by an Actress in a Motion Picture – Comedy or Musical. She earned a second Golden Globe nod for Best Actress in 2006 for her performance in the made-for-television movie “Mrs. Harris” (2006), playing the emotionally disturbed headmistress of The Madeira School for girls who made national headlines when she shot and killed her lover Dr. Herman Tarnower (Ben Kingsley), the famed cardiologist and creator of the Scarsdale Diet.