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Jean Harlow and Paul Bern -

The blonde bombshell married her first husband, a wealthy heir named Charles Fremont McGrew III, when she was only 16 and he was 21. It ended in divorce once she became successful. When Harlow was 21, she married the successful producer Paul Bern, who was 20 years her senior. The marriage only lasted two months, as Bern was found dead at their home, seemingly having died by suicide. 

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Errol Flynn and multiple young women -

A favorite saying of actor Errol Flynn was, "I like my whiskey old and my women young." The only problem was that these women were actually girls. In 1943, Flynn was accused of rape by two 17-year-old girls. However, he was acquitted. 

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Errol Flynn and Nora Eddington -

During the trial, Flynn flirted with 18-year-old Nora Eddington (pictured), who was in attendance. The then-34-year-old actor went on to marry her.

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Errol Flynn and Patrice Wymore -

After their divorce in 1949, the then 41-year-old Flynn married the 23-year-old Patrice Wymore (pictured) the following year. They stayed together till his death in 1959. 

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Frank Sinatra and Mia Farrow -

The pair married in 1966 in Las Vegas, when Farrow was 21 and Sinatra 50. They divorced in Mexico in 1968, but remained close friends until he passed away. 

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Charlie Chaplin and Mildred Harris -

Charlie Chaplin saw his first wife, Mildred Harris, when she was 12 in a film. They met when she was 15 and married the following year because she mistakenly believed she was pregnant. He was 29 years old. They divorced two years later. 

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Charlie Chaplin and Lita Grey -

Chaplin's second wife, Lita Grey, was 12 when they met and pregnant with his child by 15. He was 35. Their marriage only lasted three years. 

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Charlie Chaplin and Paulette Goddard -

At the age of 47, Chaplin married Paulette Goddard, who was 26 at the time of the ceremony in 1936. The couple divorced after six years.

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Charlie Chaplin and Oona O'Neill -

Chaplin's final and longest marriage was to Oona O'Neill, daughter of the playwright Eugene O'Neill. She was 18, and he was 54, just six months younger than her father, when they married. The couple had eight children and stayed together until his death 34 years later.

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Cary Grant and Betsy Drake -

In 1947, the 43-year-old actor was married and twice divorced when he saw Betsy Drake perform in a play in London. Within two years, they were married, despite a 19-year age difference. They divorced in 1962. 

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Cary Grant and Dyan Cannon -

Grant's fourth wife was actress Dyan Cannon, who was 33 years his junior. The couple married in 1965 and divorced two years later. Together they had his only child, Jennifer Grant. 

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Judy Garland and Vincente Minnelli -

By the time Judy Garland was 21, she was already married to composer David Rose, 12 years older than her. In June 1945, a week after divorcing her first husband, a 23-year-old Garland married director Vincente Minnelli. He was 42. They quickly had a daughter, Liza Minnelli. They divorced in 1951.

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Carlo Ponti and Sophia Loren -

Sophia Loren first met producer Carlo Ponti when she was 16 and competing in a beauty pageant. He was 38. The relationship became serious when she was 19, but they couldn't marry as Ponti was already married, and as an Italian citizen he couldn't get divorced.

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Carlo Ponti and Sophia Loren -

It wasn't until 1966 that the couple was able to legally marry after becoming French citizens. They remained married until his death in 2007.

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Lauren Bacall and Humphrey Bogart -

The iconic Hollywood couple meet on the set of 'To Have and Have Not' (1944), where they fell hard for each other. The couple married the following year in 1945. He was 45, and she was 20.

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Lauren Bacall and Humphrey Bogart -

They stayed together until Bogart's death from cancer in 1957, when Bacall became a widow at just 32 years of age.

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Douglas Fairbanks and Sylvia Ashley -

While married to fellow silent film superstar Mary Pickford, Douglas Fairbanks met the already married Sylvia Ashley (pictured). Fairbanks fell head over heels. They only married six years later, when both were finally divorced. Fairbanks was 52 and Ashley 31 at the time of their wedding in 1936. They stayed together until his death in 1939.

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Jerry Lee Lewis and Myra Gale Lewis -

Technically, a rock n' roll star rather than an Old Hollywood icon, but he did briefly dip his toes in cinema. In 1958, Lewis arrived in the UK for a planned European tour. At the airport, a reporter noticed he was with a young girl, and asked who she was. He learned she was Lewis' wife, Myra Gale Brown, and she was 15.

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Jerry Lee Lewis and Myra Gale Lewis -

Ironically, Lewis had claimed Brown was 15 in order to make their relationship seem acceptable. But in reality, she was 13, and he was 22. She was also his second cousin. By 1970, she had filed for divorce, stating that she had been "subject to every type of physical and mental abuse imaginable." They had two children. 

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Elizabeth Taylor and Michael Wilding -

Famous for marrying eight times, Elizabeth Taylor's second marriage was to actor Michael Wilding. The two were starring in a film together in 1951, and it was actually she who proposed to him. They married the following year, when Taylor was 20 and he was 40. 

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Elizabeth Taylor and Mike Todd -

Taylor left Wilding in 1957 for film producer Mike Todd, who was 23 years older than her. Todd was the third of Taylor's husbands, and the only one whom she didn't divorce. Todd died in a private plane accident a year after their marriage. 

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Elizabeth Taylor and Larry Fortensky -

Taylor married for the eighth time in 1991 to Larry Fortensky, who was 20 years her junior. The marriage ended in divorce after five years. 

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Bing Crosby and Kathryn Grant -

Bing Crosby was a widower and Kathryn Grant was just starting out in Hollywood when they began dating. She was 23 and he was 53. 

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Bing Crosby and Kathryn Grant -

The couple had three children and were married until Crosby's death in 1977.

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William Randolph Hearst and Marion Davies -

Newspaper magnate William Randolph Hearst first met Marion Davies in 1917 when she was a chorus girl in Broadway's Ziegfeld Follies. She was 20 years old and he was 54. 

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William Randolph Hearst and Marion Davies -

They quickly began a relationship, which was initially kept a secret from his wife, Millicent. Because Millicent was a devout Catholic, divorce was never an option. Eventually, Hearst began living openly with Davies. 

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William Randolph Hearst and Marion Davies -

Hearst took over management of Davies's career, but he was extremely jealous and possessive of her. Despite that, the couple stayed together until his death in 1951. Davies wasn't allowed to attend his funeral.

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John Huston and Enrica Soma -

The parents of actress Anjelica Huston, director John Huston began a relationship with Enrica Soma when she was 18. Huston was on wife number three, but that didn't stop him from getting his young mistress pregnant with a son. On February 10, 1950, the director, was in Mexico to both get a divorce and to immediately marry Soma. She was 20, and he was 45. Soma died in 1969, aged 39.

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John Wayne and Pilar Pallete -

John Wayne and Pilar Pallete first met in 1952 in her native Peru. Wayne was still married, and as the divorce dragged on, Pallete realized she was pregnant. She had an abortion to protect Wayne's image. The couple finally married in 1954. He was 47 and she was 24.

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John Wayne and Pilar Pallete -

They had three children together over a 25-year marriage. The couple never divorced, but they didn't live together for six years before Wayne died in 1979.

Sources: (Grunge) (Ranker)

See also: Mind the gap! How to handle age difference in a relationship

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