Known for: Dirty Dancing
Net worth: $10 million
Jennifer Grey was not an official “Brat Packer,” but she was an Eighties movies superstar. Besides the Dirty Dancing sensation starring opposite Patrick Swayze ( Outsiders ), Grey also starred in Ferris Bueller’s Day Off , a 1986 teen comedy. One of those era-defining flicks that continues to generate a following. During the filming, she was secretly dating Matthew Broderick (Ferris). She also dated other Eighties celebs like Johnny Depp and Michael J. Fox.
She starred in It’s Like, You Know for one season. On season eleven of Dancing With the Stars , she and her partner won the competition. In a medical exam prior to taping the show, her doctor found a suspicious mark on her thyroid. It turned out to be malignant. She had it removed immediately and has been cancer-free. Born in Manhattan to a Hollywood family, she’s the daughter of Academy Award-winning actor Joel Grey and former actress and singer, Jo Wilder, both from Jewish backgrounds. Not only that, but her grandfather was comedian and musician Mickey Katz. As a student, Jennifer Grey attended a prestigious dance and acting school located on N.Y.C.’s Upper East Side.
Winona Ryder
Known for: Beetlejuice
Net worth: $18 million
The darling of the 1980s grew up on a Northern California commune with no electricity during the 1970s. Winona Horowitz’s parents were friends with Beat poet Allen Ginsberg and Timothy Leary who is her godfather. When she was ten, the family moved to Petaluma, and she enrolled in acting classes. In 1985 she auditioned for a movie by sending a VCR recording of herself reciting a monologue she found in a J.D. Salinger novel. She didn't get the part, but the director was impressed and cast her in Lucas . It was then she decided on “Winona Ryder.” The movie was her breakout film, co-starring with Charlie Sheen.
Her goth-chick performance in Beetlejuice was undeniably lovable. In Reality Bites, she nailed eighties attitudes. She was the perfect “Jo” in Little Women. She won an Oscar nomination for The Age of Innocence and Little Women. Audiences still adore her in the sci-fi, horror, Web/TV Netflix series, Stranger Things. Ryder dated Johnny Depp, Matt Damon, and Soul Asylum’s frontman Dave Pirner. Today she’s, like, married to Keanu Reeves. Philanthropically, she’s been active supporting indigenous people’s rights.
Madonna
Known for: “Borderline” and “Like a Virgin”
Net worth: $590 million
Madonna, the primo diva of the Eighties, single-handedly made glam rock mainstream while inventing the hippest fashion trends. She was the real deal. I mean, who else would’ve thought shearing the fingertips off of lacy black gloves would create a “cool” new accessory? Her “look” and her catchy chart-busting pop songs played continuously on the radio, but more significantly, the material girl entertained over a brand-new medium. MTV. Decked out in rank new styles, Madonna’s lively singing and playful dancing to electronic-pop songs lit up the tube.
MTV and Madonna materialized during this decade of rapid technological change. Her second album, Like a Virgin, sold a record-breaking 21 million copies worldwide. On the Virgin Tour, N.Y.C. colleagues, the Beastie Boys opened up for her. Today, she’s the wealthiest woman in the music business. Madonna proved her talent on the big screen as her career progressed. She starred in Desperately Seeking Susan in 1985, a film which portrays her image. By 1992, A League of Their Own was a number-one box-office hit. Madonna played the title role in Evita (1996), for which she won many accolades and a Golden Globe for Best Actress.
Sylvia Miles
Known for: Midnight Cowboy
Net worth: $15 million
Quite possibly, the most notable event of Sylvia Miles’ career happened at the Academy Award Ceremony when she earned an Oscar nomination for Best Supporting Actress for her role in the 1969 Midnight Cowboy movie. Her role was very short. She was on screen for a total of six minutes playing Cass. Just enough time to get Joe Buck (Jon Voight) up to her penthouse for a little roll in the hay. She earned another Oscar nomination for Farewell, My Lovely .
The 1960s actress who is known to be a bit bawdy and a tad flamboyant are remembered for her role as a real estate agent in Oliver Stone’s Wall Street and Andy Warhol’s Heat. In later years, she played on Sex and the City and One Life to Live. She died on June 12, 2019. She was 94.
Dyan Cannon
Known for: Heaven Can Wait and Bob & Carol & Ted & Alice
Net worth: $16 million
Cannon’s illustrious career has spanned over five decades. It’s found her reigning amongst the royal presence of industry kings Steve McQueen, Sean Connery, Burt Reynolds, Jackie Mason, Chevy Chase, Gene Hackman, and Harvey Keitel.
Besides being nominated Best Actress by the Academy twice, Dyan Cannon produced, directed, wrote, edited and starred in Number One, a film about adolescence and sexuality. It was her third nomination for an Academy Award, Best Short Film in a Live Action Category. Most people remember her Oscar-nominated performances in Warren Beatty’s Heaven Can Wait or in the pop-culture classic, Bob & Carol & Ted & Alice which was her breakout movie. She’s also well-recognized by her marriage to leading man, Cary Grant, who was 33 years her senior when they tied the knot in 1965.