Cher

Cher's next film was a starring role in Mask in 1985, directed by Peter Bogdanovich. The film also starred Eric Stoltz, Laura Dern, Estelle Getty and Sam Elliott. It opened at #3 at the box office and was considered her first critical and commercial success as a leading actress. For her role as a mother of a severely disfigured boy, Cher won the Best Actress prize at the Cannes Film Festival and received a Golden Globe nomination for Best Actress in a Motion Picture Drama. In 1985, Cher was honored with Harvard University's Hasty Pudding Woman of the Year Award.
On May 22, 1986, Cher made her first appearance on Late Night with David Letterman. In her pre-interview with the show's producers, Cher had referred to host David Letterman with a derogatory term when asked why she had previously declined to appear on his program. He later confronted her about this on air during their interview, asking why she had refused so many earlier invitations. As she thought of an appropriate answer, he pushed her further saying, "Because you thought..." to which she replied "You were an asshole. She received a mixture of boos and laughter from the audience for the remark; however, Letterman quickly played off the incident as just fun. Cher returned to Late Night With David Letterman in an appearance on November 13, 1987, this time with ex-husband Sonny Bono, reuniting to sing "I Got You, Babe" for what would be the last time. She has since made multiple appearances on Letterman's CBS show. In 1987, Cher starred in three films. She was cast as Alexandra, the female lead in the dark comedy/fantasy film The Witches of Eastwick with Jack Nicholson, Susan Sarandon and Michelle Pfeiffer. She played a lawyer in the thriller Suspect opposite Dennis Quaid, and starred in the romantic comedy Moonstruck, which co-starred Nicolas Cage and Olympia Dukakis and was directed by Norman Jewison. For her performance as a frumpy bookkeeper in Moonstruck, she won the 1987 Academy Award for Best Actress. She also won the Golden Globe Award for Best Actress in a Musical/Comedy, and the People's Choice Award for Favorite Female Star.