We all know Grace Kelly as one of the top actresses of her time who went on to become the Princess of Monaco when she married Prince Rainier in 1956. But the truth is, she had one of the most scandalous personal lives in all of Old Hollywood. It’s all the more surprising considering how she was only 26 years old when she entered the Monaco royal family.
Ever since Kelly was a young adult, she had been in and out of scandalous affairs with much older married men, most of whom she was acting opposite in films. It was always a messy ordeal, but that never stopped the actress from acting on her heart’s desires. Take a look at all the leading actors she dated, and see why it was that the actress never settled down with any of them.
Kelly’s Family Was Rich and Successful, But She Was Always the Odd One Out
It may be hard for us to believe today, but Kelly wasn’t considered attractive when she was a child. She appeared to be the weakest-looking out of all of her siblings, with thin limbs and a shy demeanor. She was the least confident one out of her siblings, too, which made her quieter and more reserved than the rest of her family.
However, Kelly was born into considerable wealth. Unlike many other Old Hollywood stars, Kelly didn’t have to work her way out of poverty or sell her soul to the film distributors. Kelly’s father was a top-tier medal-winning athlete, and her uncle was the famous playwright George Kelly. By all account, Kelly enjoyed a privileged start to life.
She Was a Rebellious Teen Who’s Low Test Scores Got Her Rejected From College
Kelly grew up in a strictly Catholic home. But her rebellious tendencies got in her trouble with her parents throughout her teen years and ultimately resulted in tense home life. It wasn’t much better for her at school as she struggled academically, receiving bad grades that ultimately got her rejected from college.
Unlike her siblings, she avoided sports in favor of acting in plays, which was met with strong disapproval from her parents. Before long, Kelly knew she wanted to pursue an acting career and as far as mom and dad were concerned, acting was a promiscuous profession. It didn’t help that Kelly spent her teen years dating “bad boy” types of guys.
Kelly Had Hid Herself Away in Frumpy Clothes Due To Her Low Confidence
Despite becoming one of the most famously beautiful women in history, she spent her early years feeling tremendously insecure about her looks. According to those who knew her, Kelly preferred to hide away her figure in baggy clothes and cover her hair head with a scarf. She didn’t want to be the center of attention.
Kelly simply didn’t regard herself as especially beautiful, which is almost impossible to conceive of today. But with the athletic and ambitious siblings that she had, she simply wasn’t confident enough to compete with them. Of course, Kelly wouldn’t continue thinking that way for long.
Kelly Only Got More Rebellious When Her Parents Sent Her Away to the Barbizon Hotel for Women
Grace’s parents tried to change the direction of her life by sending her away to a women’s only school in New York to straighten her up. They thought that by taking boys out of her life and surrounding her with only other girls, she would focus more on her studies. Today, the Barbizon Hotel for Women is famous for having housed many celebrities before they were famous.
Despite her parents’ best intentions, Kelly didn’t walk away from the women’s only institution a changed woman. In fact, she seemed to behave even more wayward, according to accounts. She would shock the other women at the Barbizon by dancing to “Hawaiian music in the nude” or performing “wild dances in the hallway” in her underwear. She did, however, dress prim and proper and remain reserved when she wasn’t entertaining.
Kelly Seduced One of Her College Teachers and Even Dated Him For a While
Even when Kelly struggled with her confidence, others found her especially charming – even faculty members of the Barbizon Hotel. Theater director Don Richardson took a liking to the aspiring actress and felt as though there was something special about her right from the start.
Later in life, Richardson explained how “The camera did more than love her. It was insane about her – just like I was.” Despite the age gap, the pair started going out, but it wouldn’t end well for the director. He would need to get Kelly’s parents’ approval of their union in order to be with her, and they didn’t plan on her returning home from the Barbizon arm in arm with teachers.
Despite Richardson’s Best Efforts, Their Relationship Didn’t Get the Approval of Kelly’s Parents
Despite his efforts in grooming Grace Kelly’s talents, her family objected to Richardson. He did not fit in with her family: he was Jewish and ten years her senior. The relationship ended when Richardson discovered he was one of many whom she used to propel her career. Despite this, the two remained close and maintained a correspondence until Kelly’s death.
Kelly had dated other guys before, but it had never been as serious as it was with Richardson. And truthfully, he was a pretty accomplished guy – he had been a successful TV film and series director who had worked with some big-name 20th-century actors. But, he was 10 years older and not Christian like they were. Ultimately, Kelly’s parents still didn’t see him as a suitable match for their daughter and she had to break it off with him.
Kelly Was 22 Years Old By the Time That She Met and Fell In Love With Leading Man Gary Cooper
In her early 20s, Kelly’s career started to really take off. She started acting in television productions but came to the realization that she preferred performing in theater. But when she was offered a role in director Fred Zinnemann’s western movie High Noon as a young Quaker bride, she couldn’t refuse.
She was playing the part of actor Gary Cooper’s love interest, and the pair soon started to have a secret affair. Cooper once said of Kelly, “She looked like a cold dish with a man until you got her pants down, then she’d explode.” But he was a married man with a child and was 28 years her senior. This was Kelly’s first major affair with a co-star, but it wouldn’t be her last. This pattern would repeat itself many more times throughout her life.
Kelly Jumped at the Opportunity to Star Opposite Actor Clark Gable, But She May Have Had Other Intentions
Aside from her affair with Cooper, Kelly received mixed reviews for her performance in 1952’s High Noon. While she pursued private acting classes to work on her technique, her performance was well-received by director John Ford – he is said to have used the words “breeding, quality, and class” to describe Kelly. It just so happened that the leading actress for his upcoming movie had pulled out.
Ford invited Kelly to replace the leading lady in the movie Mogambo, and she was happy to take up the offer. She later explained what made her decision so easy: “Mogambo had three things that interested me: John Ford, Clark Gable, and a trip to Africa with expenses paid”. As you’ll come to see, the opportunity to star opposite Clark Gable was a big selling point.
Kelly’s Mom Flew out to Africa to Try and Chaperone Her Daughter and Stop Her From Having Another Affair
Kelly and Gable soon started having an affair. She later admitted that “If Mogambo had been made in Arizona I wouldn’t have done it,” suggesting that she had a thing for Gable before she’d even met him. Like Cooper, Gable was a lot older than Kelly – he was 30 years her senior. This angered Kelly’s mom so much that she decided to try and take matters into her own hands.
Kelly’s mom Margaret decided to fly out to their filming location in Africa to try and break up the affair. Her intention was to chaperone her daughter when she wasn’t on set, but that didn’t go to plan. Kelly and Gable continued seeing each other, but their relationship wasn’t going to last. In truth, Gable had reservations about Kelly.
Gable Wasn’t As Into Kelly As She Was Into Him, and He Dumped Her for Being Too Clingy
Kelly continued her romance with Gable behind closed doors. She may have even thought that their relationship could go somewhere, despite the huge age gap between them. But unfortunately, Gable wasn’t on the same wavelength as her. He had doubts about Kelly that just wouldn’t go away.
Allegedly, Gable found Kelly too clingy after some time and decided to break things off before they became too serious. It’s thought that Kelly suffered a broken heart when Gable called it quits, and it took her some time to get over it. As her sister Lizanne once put it, “Grace Kelly fell in love very easily; too easily.”
Alfred Hitchcock Saw Something Special in Kelly, Describing Her as a “Volcano Covered With Snow”
Kelly threw herself back into her career in order to deal with her disappointments from her affair with Gable. She ended up coming into contact with director Alfred Hitchcock, who wasn’t taken with the young actress. But his opinion about her would come to change, as he realized that there was a lot more to the starlet than initially meets the eye.
Hitchcock came to describe the actress as “A volcano covered with snow,” suggesting that he saw a fire inside of her waiting to come out. It wasn’t long before he asked her to star in one of his movies, and she accepted. But she had no idea what Hitchcock really had in store for her on set.
One Scene in Hitchcock’s Film Was Very Physically Demanding and Left Kelly Covered in Bruises
Hitchcock had other actresses in mind to star in his upcoming movie Dial M for Murder, but a friendship between him and Kelly started to bloom and he eventually found himself considering her for the role. Kelly, being so young, was very impressionable at the time, and Hitchcock found that he had a lot of control over her.
But Hitchcock put Kelly in a compromising position during the shooting of Dial M for Murder. One particular scene was more aggressive than the rest and took them five days to film. In it, Kelly’s character was put through some harsh physical challenges and it left her covered in bruises.
Kelly’s New Affair Became a Mess When Co-Star Ray Milland Left His Wife To Be With Her
Kelly was starring opposite the actor Ray Milland, are their professional relationship quickly turned romantic. They started an affair, but once again Milland was a married man with kids who was 24 years her senior. She certainly had a type and stuck to it, even though it never seemed to work out.
Milland had been married for more than two decades to Muriel Frances when he decided to divorce her in order to be with Kelly. But his plans were thwarted when Muriel told him that all of their property was listed as her own. Because of it, Milland decided to go back on his decision and return to life with Muriel, leaving Kelly behind.
One Particular Gossip Columnist Caught on to Kelly’s String of Affairs With Leading Men and Painted an Unflattering Portrait
It was bad enough for Kelly that Milland had decided to go back to his wife and leave her. But what made matters even worse was that they caught on to their affair and made Kelly out to be some kind of homewrecker. One particular gossip columnist called Hedda Hopper gave Kelly particularly bad press.
Hopper called Kelly a “Philadelphia mainline” and suggested that the actress was a nymphomaniac. All in all, Kelly was developing an awful reputation as a woman who was breaking up families and having sordid affairs with otherwise good, married men. In response, Kelly stated: “As an unmarried woman, I was thought to be a danger.”
Jimmy Stewart’s Wife Grew Paranoid of Grace Kelly and Never Let Her Husband Out of Her Sight
Kelly continued to work with Hitchcock, becoming his favorite leading lady. The next film of his that she would appear on is Rear Window acting opposite Jimmy Stewart. Kelly is said to have been attracted to Stewart, and he was very keen to work with her, too. But it was Stewart who she would end up dating.
Hitchcock once said of Kelly that “Everybody just sat around and waited for her to come in the morning, so we could just look at her.” That, coupled with the rumors about her being a homewrecker, meant that Stewart’s wife Gloria grew paranoid of their relationship. She started driving Stewart to work in the mornings, watching him shoot scenes throughout the day, and drive him back home after.
Another Movie, Another Affair With an Older Married Man While Her Career Had Never Been Better
Kelly’s career was skyrocketing. Her performance in Rear Window earned her a ton of acclaim, and MGM valued her so much that they struggled to loan her to other studios. She started working on another film called The Bridges at Toko-Ri in 1954, but the same thing happened there that had happened in lots of her other films – she started having an affair with the leading man.
Kelly was starring opposite William Holden, and the pair of them had a whirlwind romance. But, just like before, Holden was married and a great deal older than Kelly. The papers caught on to their affair at the time, but Kelly remained tight-lipped about her romantic life. She didn’t confirm or deny anything.
Kelly Started Dating Fashion Designer Oleg Cassini But Her New Leading Man, Bing Crosby, Was Falling For Her
Kelly’s affair with Holden didn’t amount to anything more serious, and they cooled things off shortly after. She started chatting to fashion designer Oleg Cassini, and their relationship soon became flirty. Before long, the two were seriously dating each other, but Cassini would have second thoughts about whether or not he could trust the actress.
She started working on a new movie, The Country Girl, after filming for The Bridges at Toko-Ri and her co-star Bing Crosby became infatuated with her. He was actually engaged to an actress called Katherine, but he fell so in love with Grace that he ended up proposing to her instead. And that wasn’t even the end of it.
Kelly Had An Affair With Bing Crosby, But Told Her Fiance That He Had Nothing To Worry About
Kelly embarked on an affair with Crosby, all the while denying that her fiance Cassini had anything to worry about. In letters later auctioned off by the Cassini estate, Kelly told her husband-to-be: “I told you he said that he was in love with me – but there are many people that he feels that way about.”
Kelly continued: “Bing would never try to do anything about it – unless he thought I wanted it that way,” ending her letter, “I have very few friends here – please don’t ask me to give up their friendships.” Even after Crosby proposed to her, they continued to have their affair. But Kelly never imagined that their relationship would end in such an awful way.
Kelly Had Captured Cassini’s Heart and Given Him the “Most Enchanting Days That I’ve Ever Had at Any Time in My Life”
While Kelly continued her affair with Crosby, Cassini was growing more and more in love with her with each passing day. She had totally captured his heart, so much so that he was willing to fly out to France to spend time with her while she was away for work.
Later in life, Cassini would come to admit, “I must say they were the most enchanting days that I’ve ever had at any time in my life,” when thinking back to his time with Kelly. Little did he know at the time that Kelly didn’t feel the same way about him, despite planning a future with him.
Kelly Broke Bing Crosby’s Heart When He Walked In on Her Sleeping With Marlon Brando
Kelly was met with critical acclaim for her performance in 1954s The Country Girl. She won an Oscar for it, but on that night, she broke Crosby’s heart for good. Crosby had just lost an Oscar to Marlon Brando and was down in the dumps. He decided to follow Kelly up to her hotel room and look for some comfort when he got the shock of his life.
When he went into Kelly’s hotel room, he found her in bed with Mr. Brando, naked. He had come to Kelly’s hotel room in the middle of the night and she wasn’t expecting him. But this was just too much for Crosby to bear, and their relationship finally ended. Crosby would go on to marry the woman he was previously engaged to.
Kelly’s Contemporaries Had a Lot To Say About Her Sordid Reputation as a Man Eater
Kelly’s public image had initially started as incredibly wholesome. But once the media found out about her several scandalous affairs, her public image completely changed. One director, Henry Hathaway, who was most famous for his Western movies starring Randolph Scott and John Wayne, once commented that Kelly had slept with “everybody,” adding “Yes, she wore white gloves but she was no saint!”
Even Kelly’s peer, actress Zsa Zsa Gabor, had something to say about the actress later in life: “She had more boyfriends in a month than I had in a lifetime. She went to bed with anyone she fancied at the time”. One Hollywood actor’s wife is also reported to have said, “I have nothing good to say about her. She had an affair with my best friend’s husband, Ray Milland!”
Kelly Secretly Had an Abortion and Eventually Dumped Her Fashion Designer Fiance
Despite Cassini’s love for Kelly, he still needed to win the approval of her hard-to-please parents. When they met the fashion designer, they were disappointed in the fact that he had been previously married and they disapproved of his Russian background. Their harsh criticism ultimately worked in encouraging Kelly to break with him, and she suffered heartbreak once more.
Her parents didn’t even know about her secret pregnancy. That’s right – Kelly had fallen pregnant with Cassini’s child but chose not to keep it. She had secretly had an abortion while she was still seeing Cassini, choosing not to tell him about it and live with the secret instead.
A Trip To Cannes Film Festival Resulted In An Invitation From the Prince of Monaco
While nursing a broken heart, Kelly attended the Cannes Film Festival in April 1955. It’s there that she met her future husband Rainier III, the Prince of Monaco when he invited her to visit him. He gave the actress a tour of his grand French palace, and the pair seemed to hit it off. Prince Rainier was single at the time and 32 years old – quite young considering Kelly’s previous age gap relationships.
On her visit, Prince Rainier showed Kelly his ornate palace gardens and his private zoo, all of which thrilled the actress. It’s thought that they stayed in touch immediately after this first meeting between the pair of them, and their romance began. Only, this one wouldn’t end up like the rest.
The Prince Wanted Kelly’s Dad To Pay Up if He Agreed To Marry Her
The meeting between Kelly and Prince Rainer went well, and the pair stayed in touch after Kelly returned to the States. Soon enough, the prince wanted to propose to the actress and asked her former Olympic gold medalist father for his daughter’s hand in marriage. But it didn’t quite go to plan.
The prince wanted her father to pay a dowry to him to marry Kelly, which was customary at the time. This caused a lot of tension between the men, and Jack Kelly Sr. is said to have felt extremely insulted. Prince Rainier was looking for a dowry of around $4 million, but eventually, Kelly Sr. agreed to roughly half of that. The money paid went towards to the construction of a new Monaco palace.
Prince Rainer Also Demanded Kelly Undergo Fertility Tests Before Confirming the Engagement
On top of the money request, Prince Rainer had another important requirement that needed to be met before he agreed to marry Kelly. He was reportedly had concerns about the actress’ fertility and wanted scientific proof that she would be able to bear him children before they were legally bound to one another.
One report even claims that he demanded a “pregnancy test” from Kelly before they wed, but that hasn’t been confirmed. It is thought, however, that the Prince of Monaco made Kelly undergo fertility tests before officially announcing their engagement, just to be sure that she could give him heirs. It certainly wasn’t shaping up to be a fairytale romance as many have been led to believe.
Kelly Wasn’t the Prince Rainer’s First Choice in Hollywood Wife, Having Previously Proposed to Marilyn Monroe
To make the proposal even less romantic, Prince Rainer had allegedly proposed marriage to another famous blonde starlet before he came to Kelly. Hollywood writer Liz Smith alleges that he was smitten with Marilyn Monroe after shipping magnate Aristotle Onassis suggested her to the Monaco royal. Onassis told Rainer that she would greatly boost his public image should she agree to the wedding.
There are a few reasons speculated as to why they never ended up tying the knot, ranging from Monroe’s jealous former husband to Monroe’s career ambitions, but either way, it ended all the same. That mean’t that he was free to ask for Kelly’s hand in marriage, but coming after another blonde Hollywood bombshell couldn’t have made her feel all that special.
Kelly Had To Abandon Her Hollywood Ambitions at the Young Age of 26
It’s been suggested by J Randy Taraborrelli, a biographer of the princess’, that Kelly only agreed to marry the prince in a bid to gain approval from her father. She had greatly disappointed him in her relationship with Oleg Cassini, and apparently, his lack of approval was a big reason behind her reluctance to marry him.
But marrying the Prince of Monaco was plenty impressive and would give Kelly her very own royal title. But being a royal wasn’t necessarily going to be like a fairytale story. For one, it required her to retire from her exciting Hollywood career at the young age of 26.
Kelly’s Wedding Day Was More of a PR Stunt, With MGM Agreeing To Pay for the Gown
When it came to Kelly’s iconic wedding gown, Metro-Goldwyn-Mayer gifted it to the actress as a wedding present. Academy Award-winning designer Helen Rose of MGM, who had previously designed costumes for the actress for movies like High Society and The Swan, designed the now iconic dress.
“The bell-shaped skirt of ivory faille, supported by three attached petticoats, fans out into a graceful lace train,” the Philadelphia Museum of Art explained. Lace embellished with pearls covers the accompanying prayer book, shoes, and cap, which is surmounted by a wreath of orange blossoms.” Apparently, the circular veil was specially designed so as to “not to obscure the bride’s famous face”. After all, this wedding was a huge PR moment for the Monaco royal family.
People Believe That Prince Rainer Was Behind Kelly’s Decision To Leave Hollywood
Kelly continued to work throughout her engagement – in fact, many believe she intended to keep working after the wedding too. But people believe that it was the prince who forced her to give it up. Only a few days after the wedding did Prince Rainer and Kelly reveal to the public that she would be stepping back from her Hollywood career.
Prince Rainier was reportedly concerned that Grace Kelly’s Hollywood career would interfere with her duties as Princess of Monaco. But aside from that, he was also said to be worried about the negative publicity that could come from her acting roles and how that could impact his own public image.
The Prince Banned All of the Movies That Kelly Had Ever Starred In In Monaco
Kelly didn’t just have to leave behind her exciting Hollywood career. On top of retiring, her new husband decided to ban every movie she had ever starred in from Monaco. Kelly’s body of work couldn’t even be enjoyed in her new country. It was the early 1950s, and the prince was allegedly unhappy with the film industry’s depiction of his country and its people.
Prince Rainer banned all films that showed Monaco in a negative light, including the work of his new American wife. Kelly’s films were among those affected by the ban, and she was unable to show her work in Monaco for many years. Kelly’s new focus was to be royal life, having children, and raising royal babies.
Kelly Was Planning To Re-Emerge Onto the Acting Scene But She Was Forced To Pull Out
Kelly looked as though she was coming out of retirement only six years into her marriage. In 1962, she was going to return to Hollywood to star in another Hitchock movie called Marnie. Monaco palace confirmed it but likewise stated, “We are certain she won’t make another film after this one.” But a few months after the announcement, the palace pulled her out of the movie.
The princess told Nice Matin, “I could only have done it if my husband and the children had come with me. This was impossible. Going on with the plan created too many problems so I called Mr. Hitchcock and said I could not do it”. Hitchcock later blamed “the conservative element in Monaco” from blocking Kelly’s return to the silver screen.
The Princess Tried To Busy Herself With Other Creative Pursuits Until She Had the Opportunity To Get Behind the Camera
Kelly was out of the acting business for all intents and purposes, it seemed. The director Herbert Ross tried to tempt her out of retirement by offering her a part in the film The Turning Point, but Prince Rainer stayed adamant that she should steer clear of acting. Instead, she involved herself in other creative pursuits over the years, such as poetry reciting.
And the princess didn’t leave the film industry entirely. Several years later, in 1976, she joined the board of the 20th Century Fox Film Corporation and brought out an independent film three years after that called Rearranged. Kelly had developed a strong interest in forestry and flower pressing, which was reflected in the movie.
Kelly Had Plans To Extend Her Independent Film Thanks To Its Positive Reception, But Tragedy Was Just Around the Corner
In fact, Rearranged was so well received after its premiere that it was requested by the network to be extended. In 1982, the princess was given an opportunity to shoot more scenes for the existing film to extend it to an hour long, which she excitedly accepted. Sadly, however, tragedy was just around the corner, and she wouldn’t live long enough to see the filming through.
The princess was driving to her Monaco home one day back from her weekend residence in the countryside when she lost control of her car and drove off a mountainside. She was taken to the hospital immediately after the accident but passed away in the night at the age of 52. Sadly, she had suffered fatal injuries to her neck and brain.
