With decreasing album sales and a lack of commercially successful singles, Cher decided to further develop her acting career.[119] While she had previously aspired to venture into film, she had only the critically and commercially unsuccessful movies Good Times and Chastity to her credit, and the Hollywood establishment did not take her seriously as an actress.[119] Cher later recalled, "I was making a fortune on the road, but I was dying inside. Everyone kept saying, 'Cher, there are people who would give anything to have standing room only at Caesars Palace. It would be the pinnacle of their careers.' And I kept thinking, 'Yes, I should be satisfied' ... But I wasn't satisfied."[120] She moved to New York in 1982 to take acting lessons with Lee Strasberg, founder of the Actors Studio, but never enrolled after her plans changed.[29] She auditioned for and was signed by director Robert Altman for the Broadway stage production Come Back to the 5 & Dime, Jimmy Dean, Jimmy Dean, playing a member of a James Dean fan club holding a 20-year reunion. That year, Altman cast her again in the film adaptation of the same title.[121] Cher credits Altman for launching her acting career: "Without Bob [Robert Altman] I would have never had a film career. Everyone told him not to cast me ... I am convinced that Bob was the only one who was brave enough to do it."[122]
Director Mike Nichols, who had seen Cher onstage in Jimmy Dean, offered her the part of Dolly Pelliker, a plant co-worker and Meryl Streep's lesbian roommate in the film Silkwood.[121] When it premiered in 1983, audiences questioned Cher's ability as an actress. She recalls attending a film preview during which the audience laughed when they saw her name in the credits.[123] For her performance, Cher received a nomination for the Academy Award for Best Supporting Actress and won the Golden Globe Award for Best Supporting Actress – Motion Picture.[121]
In 1985, Cher formed the film production company Isis.[124] Her next film, Mask (1985), reached number two at the box office[125] and was Cher's first critical and commercial success as a leading actress.[121] For her role as a drug addict biker with a teenage son who has a severe physical deformity, she won the Cannes Film Festival Award for Best Actress.[121] During the making of the film, however, she clashed with director Peter Bogdanovich. She attended the 58th Academy Awards in a tarantula-like costume "to show her scorn for the 'system'", according to authors James Parish and Michael Pitts.[121] The incident garnered her much publicity.[126]
Cher's May 1986 guest appearance on talk show Late Night with David Letterman, during which she called Letterman "an asshole", attracted much media coverage; Letterman later recalled, "It did hurt my feelings. Cher was one of the few people I've really wanted to have on the show ... I felt like a total fool, especially since I say all kinds of things to people."[127] She returned to the show in 1987, reuniting with Sonny for the last time before his death to sing an impromptu version of "I Got You Babe". According to Rolling Stone's Andy Greene, "they weren't exactly the best of friends at this point, but both of them knew it would make for unforgettable television. Had YouTube existed back then, this would have gone insanely viral the next morning." Rolling Stone listed the performance among "David Letterman's Top 10 Musical Moments" in 2015.[128]