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The following year she starred in For Keeps, a commercial success that received mixed reviews by critics but was well received by audiences. Ringwald portrayed Darcy Elliot, the editor at her high school paper, who gets pregnant by her long term boyfriend Stan, portrayed by Randall Batinkoff. The film was praised by some critics for showing the struggles of teen pregnancy. The film was met with generally negative reviews and under-performed at the box office.She was cast as Samantha Baker, a girl whose sixteenth birthday is forgotten.Ringwald's performance gained critical acclaim; many called her acting engaging.Ringwald later starred in Something to Live for: The Alison Gertz Story (1992).In 1994, she was cast as Frannie Goldsmith, in the TV adaptation of Stephen King's The Stand.

Ringwald was later featured on the cover of Time magazine on May 26, 1986.

Ringwald was set to star in another Hughes film called Oil and Vinegar; the film was scrapped when he refused to rewrite the script.

She subsequently made her motion picture debut in the independent film Tempest (1982), which earned her a Golden Globe nomination for New Star of the Year.

After appearing in the successful John Hughes films Sixteen Candles (1984), The Breakfast Club (1985), and Pretty in Pink (1986), Ringwald became a teen icon.