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Charlie Chaplin and more: 7 Old Hollywood icons married to Partners 30 years younger
ETimes.in / Updated: Jul 5, 2026, 14:55 IST
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Charlie Chaplin and more: 7 Old Hollywood icons married to Partners 30 years younger
The Golden Age of Hollywood gave us legendary performances and timeless charm. But off-screen, some of its biggest male icons had romantic histories marked by significant age differences often with partners three decades or more their junior. Here are seven stars
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Cary Grant
Cary Grant’s early marriages to Virginia Cherrill and Barbara Hutton carried modest age gaps of four and eight years. His third marriage to Betsy Drake, however, began to widen the pattern he was 45 and she was 26, a 19‑year difference. But the gap grew significantly during his affair with Sophia Loren, who was 30 years his junior, as noted by BuzzFeed. His fourth wife, Dyan Cannon, was 33 years younger when she married the 61‑year‑old actor. By his final marriage to Barbara Harris, Grant was 77 and she was 30, a 47‑year gap, the same report detailed.
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Charlie Chaplin
Charlie Chaplin’s relationships consistently involved very young partners, with the Daily Mail detailing his four marriages. He was in his late 20s when he married 16‑year‑old Mildred Harris in 1918. His second wife, Lita Grey, had first met Chaplin when she was just 8 and began working with him at 12; she was 16 and pregnant when they married while Chaplin was 35. His third marriage to Paulette Goddard carried a 21‑year gap. His fourth and final wife, Oona O’Neill, was just 18 when she married the 53‑year‑old Chaplin a difference of 35 years. The Daily Mail also noted that a US senator put forward a bill calling for investigation into his “unsavory record of law-breaking, of rape, or the debauching of American girls 16 and 17 years of age.”
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John Derek
John Derek’s second wife, Ursula Andress, was 19 when they met in 1955; he was 29, a 10‑year gap. After their separation, he began seeing Linda Evans when he was 39 and she was 23, as reported by nine.com.au. The most significant age gap came in 1973, when Derek, then 47, cast 16‑year‑old Mary Cathleen Collins (later Bo Derek) in his film, a 31‑year difference. He was still married to Evans at the time. The couple stayed in Europe until Collins turned 18 to avoid statutory rape charges in California. The Irish Mirror later quoted Bo Derek reflecting on that period: “When I look back on being 17 with a 46‑year‑old man, I thought I knew everything.” They married in 1976 when she was 19.
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Fred Astaire
Fred Astaire’s first marriage to Phyllis Potter lasted 21 years until her death; she was nine years younger. He remained a widower for decades before marrying again in 1980, when the Los Angeles Times reported that the 81‑year‑old Astaire married Robyn Smith, who was 35 and one of the first successful woman jockeys in the country, a 45‑year gap. The Deseret News added that the marriage astonished Hollywood and appalled Fred’s sister, Adele, and daughter, Ava. But it endured. They had seven years together until Astaire’s passing in 1987.
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Groucho Marx
The age gap in Groucho Marx’s marriages grew progressively wider Ruth Johnson, was a 19‑year‑old chorus girl when she married the 29‑year‑old Groucho. His second wife, Kay Marvis, was 21 when she married the 54‑year‑old comedian, a 33‑year gap. His third wife, actress Eden Hartford, was 24 when she married the 63‑year‑old Groucho, marking a 39‑year difference. All three marriages ended in divorce, as per the same source
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Bing Crosby
Bing Crosby’s first wife, Dixie Lee, was six years younger; they were together for 22 years until her death. After she passed away, Crosby had relationships with several younger women, including Patricia Neal and Inger Stevens, though those gaps were under 30 years. In 1957, at age 54, he married 23‑year‑old Kathryn Grant, creating a 31‑year gap, as reported by The Telegraph. Kathryn later recalled: “He invited me for a cup of tea… I looked into his big blue eyes and about 15 minutes later, I realised I was in love.” They remained married until Crosby’s death in 1977.
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Errol Flynn
Errol Flynn was tried and acquitted in 1942 in the alleged statutory rape of two teenage girls, according to the Los Angeles Times. During the trial, he met the teenager who ran the courthouse’s cigarette stand and later married her. The New York Post quoted Flynn’s well‑known line: “I like my whiskey old and my women young.” In his late 40s, he began a relationship with 15‑year‑old Beverly Aadland, an age gap of more than 30 years. She was with him on his yacht when he died of a heart attack at age 50.
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