Ringwald later starred in Something to Live for: The Alison Gertz Story (1992).
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This film gained generally mixed reviews despite being a commercial success. That same year she starred in Betsy's Wedding as Betsy Hopper. In 1990, Ringwald appeared in the James Scott-directed Strike It Rich alongside Robert Lindsay and John Gielgud. In the mid-1990s, Ringwald, who had been educated at a French high school in Los Angeles called Lycée Français de Los Angeles and is fluent in French, moved to Paris and starred in several French movies She returned home to the US intermittently to appear in American movies and television. In the early 1990s, Ringwald reportedly turned down the female lead roles in Pretty Woman and Ghost. The film also starred Andrew McCarthy, who previously worked with Ringwald in Pretty in Pink. The film was met with generally negative reviews and under-performed at the box office. The film was praised by some critics for showing the struggles of teen pregnancy. Her performance received positive reviews. Ringwald portrayed Darcy Elliot, the editor at her high school paper, who gets pregnant by her long term boyfriend Stan, portrayed by Randall Batinkoff. It is considered Ringwald's final teen movie. The following year she starred in For Keeps, a commercial success that received mixed reviews by critics but was well received by audiences. The Pick-up Artist focused on a womanizer who meets his match when he falls for a woman in debt to the Mafia. The film was met with mixed reviews while being a moderate commercial success. In 1987, she was cast as Randy Jensen in The Pick-up Artist, opposite Robert Downey, Jr. The film would have been about a soon-to-be-married man and a hitchhiking girl talking about their lives during the length of the car ride. Ringwald was set to star in another Hughes film called Oil and Vinegar the film was scrapped when John refused to rewrite the script. Ringwald was later featured on the cover of Time magazine on May 26, 1986. After Pretty In Pink, Ringwald planned to star in more mature roles. Ringwald was offered a role in another John Hughes film called Some Kind of Wonderful (1987) but she turned down the role as she felt it was too similar to her other films she worked on with Hughes. When first asked to be in Pretty in Pink, Ringwald was reluctant, but after seeing how hard it was for the producers to find a replacement for her, she decided she would portray Andie in the film.
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Ringwald's role as Andie went on to become one of her most recognizable performances. The following year, she was cast as Andie Walsh in another successful Hughes film called Pretty In Pink (1986). Ringwald's performance gained strong reviews. Ringwald was cast as Claire Standish, a spoiled rich, so-called sophisticate who is in detention for skipping class. Ringwald gained more success when she was cast in another John Hughes film called The Breakfast Club (1985) which was a commercial and critical success. Ringwald was regarded as a member of the so-called Brat Pack of 1980s teen actors but has said she was not really part of that group. Ringwald would later say, "It is not a good idea to do remakes of great classic films" when asked if there would be a remake to Sixteen Candles. Ringwald's performance gained critical acclaim many called her acting engaging. She was cast as Samantha Baker, a girl whose sixteenth birthday is forgotten. Ringwald rose to prominence with her breakout role in Sixteen Candles (1984).