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Every Woman Cary Grant Hooked Up With (And 1 Man)

Cary Grant, despite being one of Classic Hollywood’s most definitive leading men in the 1930s to the 1960s, never quite managed to find the true happiness and fulfillment that he spent his entire life searching for. Sure, he put off an image of being this cool and collected successful star with a debonair demeanor, a carefree approach to acting, and an impeccable sense of comedic timing, but the real Cary Grant was someone that dealt with a tremendous amount of inner turmoil.

Grant was one of the wealthiest stars in Hollywood. He owned properties in hoity-toity places like Palm Springs, Malibu, and Beverly Hills. He kept himself well-groomed, had an almost obsessive approach to tanning. And had a sense of style that even the legendary Hollywood costume designer Edith Head impressed by.

While he had all the money he could ever ask for, the nicest cars and luxury items, and mansions that would have probably even impressed the Queen, it was true love that seemed to be ever-illusive for Mr. Grant. He married five times and had flings and affairs with countless other women. It’s also assumed that he once had a lengthy relationship with a man – more on that in a bit.

In this video, we’ll be taking a look at many of the romantic relationships that Cary Grant involved in. Did he ever find true love, or did he die alone? Keep watching to find out.

Virginia Cherrill

Grant married this beautiful, tall, blonde actress in 1934. He apparently fell in love with her the frst time that they met. iHe would later say that he never once felt like their was something wrong with their love and that he knew from the beginning that she was the one that he wanted to marry.

They met at a party that he and his housemate Randolph Scott threw at the beach house they shared. The moment Grant laid eyes on Cherrill, he declared that she’s the most beautiful girl he had ever seen.

After securing her phone number, Grant began calling Virginia immediately after she left his party. When she arrived home two hours later, her mother informed her that Grant had called every ten minutes since she left the party. Today that would considered creepy and obsessive, but apparently back then that sort of thing was romantic.

From the moment that Grant and Cherrill went on their first date together, Cary basically wouldn’t let the poor girl out of his sight. Yet again, that seems like a red flag, but for Virginia, Grant’s persistence only fanned the flames of her own infatuation.

A year later, the couple tied the knot at the Caxton Hall registry office in London. Their marriage came to an end just seven months later – and even throughout that time, they repeatedly separated and reconciled.

Their bitter divorce case widely reported on in the media. Cherril demanded grant pay her $1,000 a week in benefits from his Paramount Pictures earnings.

Phyllis Brooks

After Grant started dating again, he met another tall blonde named Phyllis Brooks. At the time, he vowed to never marry again, but he and Brooks did spend quite a bit of time together vacationing in Europe in the summer of 1939. Their relationship ended later that year.

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Barbara Hutton

Grant married Barbara Hutton in 1942. Hilton was the granddaughter of Frank Winfield Woolworth, a wealthy American entrepreneur who founded the F.W. Woolworth company and started the chain of variety stores known as ‘Five-and-Dimes’.

After Woolworth passed away, he left Hutton a massive $50 million inheritance, making her one of the wealthiest women in the world in her day. The two met at a party held by Countess de Frasso in 1941.

Cary knew immediately, just as he had with Virginia, that he destined to marry Hutton. She was far different from the other women that he had dated. She sophisticated and serious, while Grant’s previous romances were more jovial types.

Cary ended up signing a prenup before they married, agreeing that he wanted none of Hutton’s fortune if and when their marriage fell apart. He wasn’t after her wealth. Cary merely wanted to make her happy – and for a while, he succeeded at that.

Four years after walking down the aisle, the couple divorced in 1945. Even though their romance had ended, the two would remain the closest of friends in the years that would follow.

Betsy Drake

Grant’s next lover was once again tall and blonde. Go figure.

And once again, he immediately knew that he was in love as soon as they met while aboard a cruise ship together. Betsy was nothing like Cary’s first wife, Virginia despite physically looking very similar. She was also quite different from Barbara.

While she came from a well-off family, she subsisted on very little money. All she wanted in life was to be an actress. At the time of meeting Mr. Grant, Drake had just finished up performing in a play in London and was sailing back to the States.

Cary wined and dined her and won over her affection. When they returned back to the US, he sponsored her career. At the time, he was under contract with RKO, and since he was one of the biggest names in Hollywood, the studio agreed to do whatever he asked.

RKO then gave Drake a contract. She was the leading lady in the films Every Girl Should Get Married and Room For One More opposite Grant. They even ended up doing a TV show together, but ultimately they didn’t have a lot of on-screen charisma.

After 18 months of dating, Grant and Drake got married in 1949. He had hoped that this third marriage would be his final and happy one, and while they did stay together for 12 years, they ended up divorcing in 1962.

Dyan Cannon

In 1965, Grant decided to give marriage yet another go when he married Dyan Cannon, an actress who was 33 years his junior. But as you should already expect by now, their marriage didn’t end up being a very long one. Two years after tying the knot, they filed for divorce. Fortunately, one good thing came out of their brief union. They had a daughter whom they named Jennifer in 1966.

Cynthia Bouron

Grant had a passionate albeit brief relationship with actress Cynthia Bouron in the late 60s. Since 1958, Grant had been feuding with the Academy of Motion Picture Arts and Sciences, but in 1970 he was selected to receive an Academy Honorary Award.

Grant made an announcement that he planned on attending the ceremony, effectively ending his 12-year boycott of the event. Two days after making this announcement, Bouron unexpectedly filed a paternity suit against Grant and stated publicly that he was the father of her 7-week-old baby girl. She even named Grant as the father of her child on her her birth certificate.

Grant requested that Bouron submit her daughter to a blood test, and after she failed to provide one, the court ordered her to remove Grant’s name from the birth certificate.

Barbara Harris

Between 1973 and 1977, Grant dated a photo journalist named Maureen Donaldson. He then briefly dated the much younger socialite Victoria Morgan.

Seeking out yet another partner who was substantially younger than he was, Grant married his fifth wife, Barbara Harris in 1981. Harris was a hotel public relations agent who was 47 years younger than Grant was. They met in 1976 at the Royal Lancaster Hotel in London, which was where Harris was working at the time.

Their relationship started out as a friendship, but in 1979, Harris went out to California to live with Grant. Everyone that saw Grant and Harris together noted that Harris seemed to have a positive impact on him. Prince Ranier of Monaco even was quoted as saying that Grant had never been happier.

Five years after getting married, Harris was made a widow when Grant died at the age of 82 in 1986.

Randolph Scott

On and off for 12 years, Grant lived with his companion, fellow actor Randolph Scott. The two had met early on in Cary’s Hollywood career in 1933 on the Paramount lot while Scott was filming the drama film Sky Bride. Grant was filming Sinners in the Sun at the time, and after they both wrapped up their projects, they moved in together.

While some claim that there is no evidence to suggest that the two stars were romantically entangled. It was widely speculated in Tinsel Town back in those days that Grant was bisexual.

One of the two actor’s mutual friends, Scotty Bowers, claimed in his autobiography, Full Service, which was published after Grant’s death, that he had sexual affairs with both Cary and Randolph.

Years before he met Scott, Grant lived with the openly gay Hollywood designer Orry-Kelly. Grant’s bisexuality was also the focus of the film, Women He Undressed.

In the 20s and early 30s, Hollywood was pretty tolerant of gay stars and their relationships. But the professional and cultural climate would quickly change to being a lot more oppressive and repressive soon after that.

This change likely led to Grant making a more significant effort to hide his sexuality. Even so, Grant’s former wife, Betsy Drake, and his daughter Jennifer have both disputed claims that Grant was gay.

It’s fascinating to think that even for stars as rich and famous as Cary Grant, happiness is still just as elusive as it is for anyone else. Grant had an estimated net worth at the time of his death of about $60 million. In today’s figures, that’s equal to roughly $130 million. But even though he was as loaded as he was, all of that money wasn’t capable of buying him the one thing that he seemed to want most in life, true love.

At least according to his friend’s, he was relatively happy in his final years while married to his fifth wife.

Did you know that Cary Grant was married as many times as he was? And were you aware that he spent 12 years allegedly having a romantic relationship with Randolph Scott? Share your take on things with us in the comments.

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