Oscar-nominated for her supporting turn as Masha, Olin continued her penchant for films with a background of political upheaval, acting opposite Robert Redford in the Sydney Pollack-directed "Havana" (1990), a disappointing "Casablanca"-like tale of Cuba in the late 50s, perhaps unjustly maligned as a complete bomb. After making her New York theater debut with a moving turn as the tormented titular character in a 1991 Swedish-language production of "Miss Julie", directed by Bergman, she returned to the screen opposite Richard Gere in the dubious "Mr. Jones" (1993). She fared far better as the standout of that year's "Romeo Is Bleeding", playing her most outrageous role to date, a psychopathic, Russian assassin (with thighs of steel) who even cuts off her arm to evade capture. She also sandwiched two European flicks, the moribund "The Night & the Moment" (1994) and the slick Swedish actioner "Hamilton" (1998), around Sidney Lumet's "Night Falls on Manhattan" (1997), in which she romanced Andy Garcia.

In Teresa Connelly's "Polish Wedding" (1998) she relished her role as a strong-willed mother of five who, although her family means everything to her, still tries to capture the excitement of her youth through illicit love. Olin had a small role as psychiatrist to Casanova Frankenstein (Geoffrey Rush) in the superhero send-up "Mystery Men" (1999) and then performed her determined hellcat routine with gusto as a leader of a satanic cult for Roman Polanski's "The Ninth Gate", its US release moved back three months to March 2000 to give a little more separation between it and another supernatural picture also starring Johnny Depp, Tim Burton's "Sleepy Hollow".