Old Hollywood Relationships With Controversial Age Gaps

May-December relationships — ones with particularly large age gaps — are not unexpected in Hollywood. Even in the modern day, fans are used to seeing older celebrities date people young enough to be their children or even grandchildren. And in those that are heterosexual relationships, it is almost always the man who is much older. This was also the case in the days of Old Hollywood.

There seem to be very few, if any, Old Hollywood relationships where the woman was significantly older. One exception could be Dolores del Rio and Orson Welles. The first Mexican superstar in Hollywood was 11 years older than the multi-hyphenate Welles. According to Vanity Fair, he saw her in a film in 1932 when he was about 17 years old and would later say, "That's when I fell in love with her. It changed my life." After finally meeting at a party in 1939, the pair began a relationship that lasted several years before it imploded.

While 11 years is not an insignificant age gap, it pales in comparison to many other relationships from the time. While some female stars of Old Hollywood would go on to date younger men in their later years during the 1970s and '80s, when it came to the Golden Age of Hollywood, it was older men dating and marrying younger women — in many cases, too young.

Charlie Chaplin and several wives

Charlie Chaplin, born in 1889, married four times. Three of those wives were teenagers, two of them underage. His first wife, Mildred Harris, told her version of their meeting in a syndicated newspaper article in 1927. She wrote he'd seen her in a film when she was 12, and met her when she was 15. While they began a relationship, Harris admitted she was still very young mentally as well as in age. They married when she was 16 because she mistakenly believed she was pregnant, then divorced two years later.

Chaplin's second wife, Lita Grey, was 12 when they met and pregnant with his child by 15. Their subsequent marriage also only lasted a few years. In 1932, first wife Harris told a reporter (via The Vancouver Sun) in regards to the two divorces, "Too much sweet 16 — that's Charlie's trouble. What he needs, to be really happy, is a woman of about 30, a woman with a full knowledge of human nature..." Chaplin would almost take that advice when he married the third time, to the comparatively ancient Paulette Goddard, who was about 25 at the time of the ceremony in 1936. Regardless, the couple divorced after six years.

His final and longest marriage by far was to Oona O'Neill (pictured), daughter of the playwright Eugene O'Neill. She was 18 and he was 54 (just six months younger than her father) when they married, and they stayed together until his death 34 years later.

Jean Harlow and Paul Bern

Jean Harlow was the blonde bombshell of 1930s Hollywood. Her first marriage, while still a teenager, ended in divorce once she became successful. Harlow secured the role that would take her to superstardom in the 1932 film "Red-Headed Woman," thanks to the successful producer Paul Bern, and the pair began a relationship.

On July 2, 1932, the couple married in a ceremony that seemed to take Hollywood by surprise — not because of the age difference but because no one ever thought Bern would give up his bachelor lifestyle. "Paul Bern: The Life and Famous Death of the MGM Director and Husband of Harlow" by E.J. Fleming, notes that the Los Angeles Times did pointedly mention the age gap, however, quoting the paper, italics and all, that the "wedding ... climaxed a romance in which Miss Harlow, now 21, took as her husband a man considerably her senior..." Born in 1889, Bern was 41 at the time of their wedding.

The marriage lasted two months. On September 5, Bern was found dead at their home, seemingly having died by suicide. However, questions would quickly be raised when police discovered he had married a woman named Dorothy Millette many years before — and they had never divorced. In fact, he regularly sent her money and they corresponded often. She was in California at the time of his death, and when she died by suicide shortly afterward, some wondered if she'd had something to do with it.

Douglas Fairbanks Sr. and Sylvia Ashley

Often called Hollywood's first power couple, Douglas Fairbanks and Mary Pickford were silent film superstars who were not only actors but producers who co-founded the successful United Artists company with Charlie Chaplin. The pair had left their respective spouses to marry in 1919, but by 1931, there were cracks in the relationship. 

Then Fairbanks attended a party and met Lady Sylvia Ashley, the wife of the Earl of Shaftsbury's heir, Anthony Ashley-Cooper. Fairbanks fell head over heels. In "Pickford: The Woman Who Made Hollywood," Eileen Whitfield writes that by this point Pickford was 39 to Ashley's 26, and the actress felt she couldn't compare to the latter's beauty. For the next two years, Fairbanks jerked his wife around emotionally, until he finally sent her a message from Europe that he wasn't coming back. Pickford leaked the telegram to an infamous gossip columnist and filed for divorce in 1933. The following year, Ashley-Cooper divorced his wife and named Fairbanks as the reason.

Fairbanks and Ashley married in March 1936 when they were 52 and 31, respectively. According to "The Grit in the Pearl: The Scandalous Life of Margaret, Duchess of Argyll," by Lyndsy Spence, the titular duchess was friends with the couple, but believed he was "pathologically jealous" of his wife and barely let her out of his sight, to the point Margaret found it unreasonable. Despite this, they stayed together until his death in 1939. Ashley would marry three more times; husband No. 4 was Clark Gable. 

Humphrey Bogart and Lauren Bacall

Lauren Bacall's first film role was opposite Humphrey Bogart in "To Have and Have Not" (pictured). In 2011, Bacall told Vanity Fair that when she met the Hollywood star before filming began, "There was no clap of thunder, no lightning bolt, just a simple how-do-you-do. ... he seemed a friendly man." But very quickly during the shoot, the pair fell for each other hard. 

The age difference between the then-teenager and the middle-aged man was not what stopped them from getting married — it was the fact Bogart already had a wife, Mayo Methot. Methot had problems with alcohol (Bogart was also a notoriously heavy drinker) and that combined with her intense jealousy had already led to her stabbing her husband once before. Eventually, Bogart was able to obtain a divorce, fortunately with no bloodshed.

Bogart and Bacall married in 1945; he was 45 and she was 20. As for their age gap, Bacall explained to the outlet, "Bogie was 25 years my senior... I knew everybody because I was married to Bogie, and that 25-year difference was the most fantastic thing for me to have in my life." However, their relationship actually hurt her career, since he wanted her to be a traditional wife more than a working actress. Although both had, at the very least, emotional affairs with others during their marriage, they stayed together until Bogart's death from cancer in 1957, when Bacall found herself a widow at just 32 years old.

Errol Flynn, two of his wives, and several underage girls

According to The Hollywood Reporter, a favorite saying of the swashbuckling actor Errol Flynn was, "I like my whiskey old and my women young." The only thing incorrect about it was calling the objects of his desire "women," since usually they were girls. In many cases criminally so.

In 1943, Flynn was accused of rape by two 17-year-old girls. Despite being acquitted, he later wrote in his autobiography (via Vanity Fair), "I might have been guilty as hell — under the law, that is. But in the world of day-to-day common sense ... everybody knew that the girls had asked for it, whether or not I had my wicked ways with them." During the trial, he'd flirted with an 18-year-old who'd attended, Nora Eddington, who the 34-year-old actor would subsequently marry. After their divorce in 1949, the now-41-year-old Flynn married the 23-year-old Patrice Wymore (pictured) the following year.

Flynn died suddenly in 1959, aged 50, while on a trip to Canada with his 17-year-old mistress Beverly Fisher, whom he'd been seeing for two years at that point. When they'd landed in the country, a reporter at the airport asked Flynn why he liked young girls so much, to which the actor gave an extremely vulgar retort.

William Randolph Hearst and Marion Davies

Newspaper magnate William Randolph Hearst first saw Marion Davies in 1917 when she was dancing as a chorus girl in Broadway's Ziegfeld Follies. She was 20 years old; he was 54. According to "Captain of Her Soul: The Life of Marion Davies" by Lara Gabrielle, what started as phone calls turned into regular meetings. Soon he was sending her expensive gifts. But their relationship had to be kept a secret from his elderly mother and his wife, Millicent. Because Millicent was a devout Catholic, divorce was never an option. Eventually, the affair was impossible to hide from her, and Hearst began living openly with Davies, especially at his estates in California.

The almost 34-year age difference between the couple led Hearst to the point of irrationality. In 1925, he hired a detective agency to tail Davies and send him detailed reports of everything she did and everyone she saw when he was away. Davies' close friendship with Charlie Chaplin was especially concerning to Hearst, and he sent at least one letter breaking up with her, writing that she was welcome to Chaplin, whom he called "a dirty little ignorant cockney clown."

However, despite his jealousy, the couple stayed together until his death. During that time, Davies had an impressive career of her own, becoming renowned for her comedic abilities, producing films herself, and even loaning Hearst $1 million when his company was in trouble. When Hearst died in 1951, Davies was not allowed to attend his funeral.

Elizabeth Taylor and several husbands

Elizabeth Taylor famously married eight times, twice to the actor Richard Burton. But before "Liz 'n' Dick" was a thing, she married husband No. 2, the actor Michael Wilding (pictured). The two were starring in a film together in 1951, and it was actually she who proposed to him. According to "The Life of Elizabeth Taylor" by Alexander Walker, Wilding had not wanted to marry her because legally she wasn't old enough to walk down the aisle without her parents' permission; meanwhile, she caked on makeup in an attempt to look older for him. When they finally married the following year, Taylor was 20 and he was 40. As she told LIFE years later, "With Michael Wilding, who was much older than I was, I wanted the calm and quiet and security of friendship."

With all the focus, even long after their divorce in 1957, on Taylor's age gap with Wilding, it's quite odd that the man she left him for was actually three years older than he was. But while Wilding showed his age in look and action (or rather, inaction), husband No. 3, the film producer Mike Todd, was a ball of non-stop energy. This probably explains why the 23-year age gap seemed less of an issue in their marriage than the 20 years that separated Taylor and Wilding.

Later in life, Taylor would be the December half of a May-December romance when she married for the eighth time in 1991 to Larry Fortensky, who was 20 years her junior.

Bing Crosby and Kathryn Grant

Bing Crosby was a widower and Kathryn Grant was just starting out in Hollywood when they began dating. Grant told Smashing Interviews Magazine that their marriage was a long time coming: "We kept meeting each other, and then we'd plan to get married, and he would have a kidney stone or something dreadful like that. We kept waiting, and I kept working. Later on, we finally managed to get married, which was a secret." The couple married in Las Vegas in 1957, and Grant revealed that when the press figured out the ceremony was going to happen imminently, Crosby told the reporters it was at a location hours away from the actual church, which allowed them to have a quiet, private wedding. She was 23 and he was 53 — and balding, as a syndicated newspaper report on the ceremony (via the Columbia Missourian) unnecessarily pointed out.

The 30-year age gap was clearly noticed, but when asked if she was constantly dealing with people commenting on it at the time, Grant said, "I suppose that happened, but I didn't hear it. By the time we had courted, I knew I liked him very much, and he liked me very much. By the time we married, I realized I could survive without him, and he realized he didn't want to survive without me. I liked that. That's a good attitude to enter a marriage with." The couple had three children and were married until Crosby's death in 1977.

Carlo Ponti and Sophia Loren

Actor Sophia Loren and producer Carlo Ponti were married from 1966 to his death in 2007. When asked about the secret to such a long marriage, she told The Sydney Morning Herald, "No secret. It was love at first sight for both of us. We met at a beauty contest in Rome when I was 16 and he was on the jury. He saw me sitting at a table with friends and sent me a note asking me to join the contest. I did and I finished second, but the most important thing was that this was how we started to see each other, at first in a friendly way, then it became serious when I was 19 ... We genuinely loved each other." At the time they met, Ponti was 38.

Their ability to get married, however, was hampered because Ponti was already married, and as an Italian citizen it was almost impossible for him to get a divorce from his first wife. In 1957, he attempted to obtain both a divorce by proxy from his wife and a marriage by proxy to Loren using the Mexican courts. But according to Italian law, the divorce didn't exist, while the second marriage did, so Ponti was considered a bigamist. He then got the marriage to Loren annulled, which the Italian government agreed was valid but said he could still be charged since he had already committed bigamy. It was not until 1966 that the couple was able to legally marry after becoming French citizens. 

Cary Grant and Betsy Drake

By the time Cary Grant saw Betsy Drake perform in a play in London in 1947, he was 43, married and divorced twice, and one of the biggest movie stars in the world. When they ended up taking the same ship back to the U.S., they struck up a conversation and within two years they were married, despite a 19-year age difference.

Their marriage saw him try but fail to retire from Hollywood, and she introduced him to LSD. But by 1956, when Grant left to film in Europe with Sophia Loren, their marriage was falling apart. It probably didn't help that Grant fell in love with the 22-year-old Loren, who by then had been involved with her much older future husband Carlo Ponti for several years. Regardless, the still-married Grant proposed, although the young actress must have turned him down. Grant didn't even leave set to be by his wife's side when the ocean liner she was on sank after hitting another ship, killing 51 people but leaving Drake uninjured. Not long after, Grant and Drake separated, although they didn't end their marriage until 1962.

Despite their divorce, Grant and Drake remained very close. He told The New York Times in 1973, "I'll be talking to Betsy later today, as a matter of fact. She's applying for her doctorate in psychology at UCLA. Betsy was a delightful comedienne, but I don't think that Hollywood was ever really her milieu. She wanted to help humanity, to help others help themselves."

John Houston and Enrica Soma

When the actor Anjelica Huston was asked by Vulture for her thoughts on May-December relationships, she said, "I think there are some younger women with older guys who love them and stay with them forever. I don't know. I think it depends on the case." One case study she saw close up was that of her parents.

The director John Huston met his future wife Enrica Soma when she was 14. According to Anjelica in her memoir (via Vanity Fair), they met at Soma's father's speakeasy. John said to the ballet-loving teenager, "I'll tell you what. I'll take you to the ballet... How about that?" Fortunately, the date never happened and the two did not begin a relationship until they met again at a dinner party a few years later. By then, Soma was 18. John was on wife No. 3, but that didn't stop him from getting his young mistress pregnant with a son. February 10, 1950, ended up being a busy day for the director, as he was in Mexico to both get a divorce and get remarried immediately afterward. Soma was 20; John was 45.

Their marriage was far from a fairytale. Soma had a third child, Allegra, who was raised believing John Huston was her father until the truth that her mother conceived her when she had an affair with an English lord was sprung on her at age 12. The couple never divorced, however. Soma died in 1969, aged 39.

Vincente Minnelli and Judy Garland

Judy Garland was thrown into Hollywood when she was barely a teenager. By the time she was 21, she was already married to composer David Rose, 12 years older than her, but she had her eye on producer Joe Mankiewicz, 13 years older than her and also married. But when she started filming "Meet Me in St. Louis," directed by her future husband Vincente Minnelli, Garland began a relationship ... with her male co-star. In fact, if anything, Minnelli drove her crazy with his direction which was both vague and exacting, requiring far more takes than Garland was used to requiring to nail a scene. 

Garland, Minnelli, and a few other people from the set would often have dinner together, usually just as a break from working. But one night, cancellations meant it was just the two of them, and it must have gone well, because after that the private dinners continued. Of course, Garland was still married to Rose at this point, and there were other complications as well, namely that she started up an affair with Mankiewicz again, and that Minnelli was gay. While plenty of people allegedly told Garland this fact, she ignored it.

In June 1945, a week after divorcing her first husband, Garland married Minnelli in a small, private ceremony. She had turned 23 just days before; he was 42. They quickly had a daughter, Liza, but the issues they had ignored (including Garland's affair with Orson Welles during her engagement to Minnelli) doomed the marriage, and they divorced in 1951.

John Wayne and Pilar Pallete

John Wayne and Pilar Pallete began a relationship when she moved to Los Angeles, but they had actually met once before, in 1952 in a jungle in Peru. She was starting out as an actress and filming a scene that involved dancing and fire. Wayne was impressed. He was also in a toxic marriage to his second wife, Esperanza Baur. When they finally divorced, she accused him of abuse and he accused her of infidelity. Of course, Wayne had been unfaithful as well. While the divorce dragged on, Pallete realized she was pregnant, and decided to have an abortion in part to protect Wayne's image. The couple finally married in 1954; he was 47 and she was 24.

Pallete told the Los Angeles Times in 1987 that despite being 23 years older than her, Wayne "seemed like a lot younger man. He used to like to water ski. He loved the boat, he loved to dance — he was a wonderful dancer — and we had a lot of fun together."

They had three children together over a 25-year marriage. The couple never divorced, although their relationship had its own problems and they didn't live together for six years before Wayne died in 1979. He also left Pallete out of his will, although his lawyers were quick to point out, according to The New York Times, this wasn't meant to be cruel, but that when they had separated he'd already given her a settlement. 

Jerry Lee Lewis and Myra Gale Lewis

Jerry Lee Lewis was technically a rock 'n' roll star rather than an Old Hollywood icon, but he did dip his toe into the latter world as well. In 1958, he had a cameo in the film "High School Confidential!," which, despite being terrible, starred many famous names, including John Barrymore and Charles Chaplin Jr. It was a small start, but according to Rolling Stone, people saw his career trajectory as a possible rival to Elvis Presley, which probably would have meant starring in his own movies.

The same year that film was released, Lewis arrived in the U.K. for a planned European tour. At the airport, a reporter noticed a very young girl in his entourage and asked who she was and how old was she? He learned she was Lewis' wife, Myra Gale Brown, and she was 15. While that revelation was shocking to the British public, ironically, Lewis had claimed Brown was 15 in order to make their relationship seem acceptable. In reality, she was 13. He was 22. Oh, also, she was his second cousin. And since he hadn't been divorced from his first wife when he married Brown, he had committed bigamy.

Any dreams of a Hollywood career rivaling Elvis' were destroyed at that moment, and it would be a decade until he attempted a comeback. Surprisingly, the marriage lasted until 1970, when Brown filed for a divorce and accused Lewis of abuse and adultery. 

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