How Barbi Benton Stole Hugh Hefner’s Heart Before Disappearing From the Limelight for Good

Fri Mar 04 2022

Barbi Benton was once one of the most famous women in the world. Known for being stunningly beautiful and hugely talented, this model, Playmate, actress, and singer had guys lining up around the block to date her. But it’s safe to say that there was one man who wanted her more than most… and he was going to stop at nothing to get her.

Although Barbi Benton secured the affections of the most eligible bachelor in the world, Hugh Hefner kept his true feelings for the model close to his chest. But what many people don’t realize is just how much the man in the velvet robe was willing to sacrifice for the woman he loved – or how his love affected her decision to remove herself from the world of fame and fortune for good. This is the story of Barbi Benton, her tainted love affair, and why she left the entertainment world forever.

Barbi Had No Intention of Becoming Famous When She Was Younger, and Thought She Was Going to Live a Normal Life

Barbi Benton – born Barbara Lynn Klein in 1950 – never imagined her life to pan out the way that she did. In fact, she never had any intention of becoming famous when she was younger. She spent the first two years of her life in New York City, but even when her family moved to West California in 1952 she had no desire to explore the bright lights of Hollywood.

In her eyes, she was just a normal kid who was going to have a normal life just like her well-respected parents. She thought that she would make her way into the professional world and follow in the footsteps of her father, a gynecologist, or her mother, an investment counselor. Little did she know that she’d end up with one of the most famous men alive.

She Originally Wanted to Be a Veterinarian, but Decided Against It Because She Had a Weak Stomach

After weighing up the ideas of her parents’ professions, Barbi Benton eventually decided that she wanted to be a veterinarian. She was a smart child and got perfect grades at high school. Plus, she had a keen interest in animals and helping others, and it seemed like a natural step for her. So, she enrolled at UCLA to make this dream a reality.

Although Barbi was excited to get the ball rolling on her veterinary career, a few months into the veterinary course she realized that she may have made the wrong decision. In 1980 she told People that “I had to give up when I realized I couldn’t stand the sight of blood.” But her weak stomach wasn’t going to stop her from getting a college education, so Barbi continued her studies… until she met Hugh Hefner.

Barbi Developed an Interest for Modeling in High School, and Decided to Pursue a Modeling Career While at College

Throughout her life, Barbi had been told by almost everyone she met how beautiful she was. With her brown locks, her striking eyes, and her dazzling smile, she stood out from the crowd. So, when she was 16 years old she developed an interest in modeling and even took a class called “tearoom modeling” while at high school. At the time, she just thought it was something fun. She didn’t see it as a career for herself.

However, when Barbi made the decision that she no longer wanted to be a veterinarian, she opted to re-think the prospect of being a full-time model. Although she maintained her studies at UCLA, she thought she’d at least dip her toe into the world of professional modeling. It was this decision that changed her life forever.

After a Few Commercial Gigs, Barbi Was Offered the Chance to Star on Hugh Hefner’s TV Show Playboy After Dark

Before too long, Barbi had landed herself a spot with a commercial agency. Within just a few weeks she was featured in some of the biggest television commercials in the United States – and her looks and her talent made her stand out from the crowd. So much so that she was scouted for one of the most popular TV shows around.

In 1968, when she was still just 18 years old, Barbi Benton was offered the chance to star as an extra on Playboy After Dark. Hosted by Hugh Hefner, this television show featured his famous Playboy Playmates as they let loose and had a party for all at home to watch. They were often joined by celebrity guests – often singers – who would also perform for them. It was here that she met the man himself.

As Barbi Studied in Between Takes on the Set of the Show, She Attracted the Attention of Hugh Hefner

Despite the fact that Barbi had been booked as an extra on one of the biggest shows of the late ’60s, she still wanted to continue her studies. So, she decided to juggle her responsibilities and fit in some revision time in between takes on the set of the show. She hoped that she would be able to blend into the background when she did this, but in actuality it made her stand out even more.

On just her second day in the studio, she was noticed by none other than Hugh Hefner himself. Hugh had landed himself a Bachelor of Arts in Psychology and a double minor in Creative Writing and Art before he founded Playboy magazine, and he appreciated those who were willing to better themselves through study. So, Barbi was intriguing to him. After spending a few minutes plucking up the courage, he went over to her and introduced himself.

Hugh Was Intrigued by Barbi’s Intelligence and Devotion to Her Studies, so He Plucked up the Courage to Ask Her Out

Although Hugh was constantly surrounded by women and Playboy Playmates, Hugh could tell that there was something different about Barbi. Unlike the other extras on the show, she wasn’t trying to charm her way to the top – she was obviously just there for the opportunity, and to study for her college degree.

Barbi told People that “He came up to ask me what I was so diligently working on. I told him I was studying for school. He liked the fact that I was co-ed and that I went to UCLA. We were talking about my schooling and what I was studying, and he asked me if I would go out with him.” But Hugh was used to women saying yes to his advances, which is why Barbi’s decision caught him off guard.

Barbi Didn’t Feel Comfortable With the Age Difference Between Them, and She Had Other Men Wanting to Take Her Out

When Hugh asked Barbi out for the first time, she was still 18 years old – while he was 42. She knew of his reputation and she knew that he was much older than him, so she was unsure of what to say in response. The question had come completely out of the blue, and she was still not used to being around someone so famous.

In the end, Barbi replied, “I don’t know, I’ve never dated anyone over 24 before.” Hefner seemed to be expecting such a response, as he quickly quipped back with “That’s all right, neither have I.” But what Hugh didn’t realize was that he wasn’t the only one vying for Barbi’s attention. Although she was still young and relatively new to the world of entertainment, other men already had eyes on her.

Barbi Had Two Other Men Asking Her Out at the Same Time, so She Didn’t Know Who to Choose

Although Barbi was flattered by the advances of Hugh Hefner, she wasn’t as flattered as the Playboy founder expected her to be. That’s because she had two other men who wanted to take her out at the same time, and so he was just one of three men she could choose from – if she chose to date any of them at all.

Not only was Benton’s former college boyfriend trying to get her back, but her short entrance into the limelight had also caught the attention of actor James Caan, who had risen to fame in movies like El Dorado, Journey to Shiloh, and The Rain People. All of the men were completely different and had their own quirks… but who would she choose?

Barbi Chose to Go Out With Hugh, and Before Too Long She Was Promoted to Co-Host of Playboy After Dark

After weighing up her options and getting to know the men who were asking her out better, she found herself being drawn more and more towards Hugh Hefner. However, she was cautious about getting too close to him. He was a notorious bachelor and his reputation preceded him, which is why she only agreed to go out on a date with him if there was a whole group of them going.

In the end, Hugh and Barbi went out with writer Shel Silverstein on their day – but Barbi wasn’t impressed with their “group” and didn’t like Shel at all. That didn’t stop her from forming a connection with the Playboy founder, though. Barbi saw what the bachelor was really like behind closed doors, and she liked what she saw. They formed a relationship, and within a few weeks, she had been promoted to the co-host of Playboy After Dark.

As Their Relationship Progressed, Hugh Convinced the Model to Change Her Birth Name to a Stage Name

As news of the model’s relationship with Hugh Hefner went public, she became a celebrity overnight. But at that time, she was still modeling under her birth name of Barbara Lynn Klein. As her boyfriend, Hugh wanted to be there for her on a personal level, but he also wanted to help her out professionally – which is why he decided that she needed to change her name.

In his professional opinion, Barbara Klein wasn’t the name of a star, so he wanted to make her more desirable and more marketable in the world of showbusiness. He reportedly encouraged her to change her name to Barbi Benton, and she agreed. With this new name in tow, Barbi was ready to take over the world with Hugh Hefner by her side…

Barbi Became Hugh’s Official Girlfriend, and Became a Leading Icon of the Playboy Magazine Era

By this point, everyone wanted to know more about Barbi Benton. She had become Hugh Hefner’s official girlfriend, and the whole concept intrigued fans of the magazine. After all, Hugh didn’t have girlfriends – he had Playboy Playmates and lots of them. So, what was so different about Barbi? That’s what everyone wanted to know.

Like the Playmates, Barbi still had her part to play in the Playboy legacy. She lived with Hugh in his home, and she even landed her first Playboy cover in 1969. But as someone who had never intended to be famous or to be a model, the whole experience was strange. She noted that during her first photoshoot “I was shy and would make the photographer turn his back when I changed poses. By the second one, I just let it all hang out.”

As Barbi Became More and More Famous, Many Questioned How She Could Be With Such an Infamous Bachelor

After being lifted up by the success of her modeling career, Barbi made her transition into the world of movies and television. Her most notable role came in 1970 when she starred in the musical variety show Hee Haw, which allowed her to show off her acting and singing talent. However, as she became more famous and people learned of her relationship, she was inundated with questions. For the most part, fans just didn’t understand.

While many questioned Hugh’s devotion to Barbi, she was content in their relationship. She noted that “He was one of the most romantic men I’ve ever met. Was always rubbing my neck, holding my hand, squeezing me, and making me feel loved. He was also affectionate with other girls… and he loved kissing. I didn’t mind, because I was very secure in our relationship.” But did his wandering eye prove too much for Barbi to bear as the years went by?

It’s Been Confirmed That Barbi Encouraged Hugh Hefner to Buy the Iconic Playboy Mansion In the First Place

Today, Hugh Hefner’s Playboy legacy surrounds the infamous Playboy Mansion. This is where he lived with his Playmates, this is where he hosted his iconic parties, and this is even where he passed away. And while it’s assumed that Hugh found and bought this mansion for himself, he actually has Barbi Benton to thank for it.

After learning that the mansion was up for sale, Barbi convinced Hugh to take a look at it – with her mom working as the realtor for the deal. While Hugh could see the appeal of such a property and was willing to buy it, he would only put pen to paper if Barbi did one thing… She would have to live there with him. He told her that if she didn’t, he wouldn’t buy it.

Barbi Lived With Hugh in the Playboy Mansion for Another Nine Years, Where She Was Exposed to the High Life

By this point in their relationship, Barbi was in love. Hugh had won her over, she’d come to love his intelligence and his quirky personality, and, at that time, she didn’t mind that his job meant that he was surrounded by other women. She was the one that he’d asked to move in, and she was the one he’d chosen. So, she moved in.

Over the next nine years, the Playboy Mansion became a hive of activity. Barbi noted that “Everybody who was anybody was there. Warren Beatty was a regular, Sammy Davis, Jack Nicholson, Tony Bennett, Tony Curtis. The list is endless. Anybody that was famous found their way to the Playboy Mansion. It was exciting for me. But I didn’t know half of them!”

While Her Life Was on Track, Barbi Even Made Her Mark on the Music Industry as a Singer

During the 1970s, Barbi’s life seemed perfect. Women around the world were jealous of her and she had fame, fortune, and the man of her dreams. Doors were also opening up for this all-talented woman, and after displaying her musical talent in Hee Haw, Barbi decided to properly venture out into the professional music world.

In 1974, she released her very first country and western album, Barbi Doll, which included songs like “Brass Buckles” and “Movie Magazine, Stars in Her Eyes.” While this album was not an immediate success, it did make its way to number 17 in the Country Music Charts. She released three more albums in the late 1970s – but then something in her shifted and she began to question everything in her life.

In the Late 1970s, Barbi Began to Question Her Relationship With Hugh and Struggled With His Infidelities

Although it seemed as though Barbi had won at life, her place in the limelight began to take its toll on her after a while. As someone who had never wanted to be famous in the first place, she felt the pull of the entertainment world to be exhausting – and she was also struggling to cope with her boyfriend’s infidelities.

While Barbi originally knew that, despite Hugh’s wandering eyes, he wanted to be with her, she started to question whether that was still true. The world saw him as a bachelor and they saw him as the ultimate womanizer, and she began to see him in the same way. Was their relationship all a farce? Was she just another one of his many Playmates?

In an Attempt to Keep the Love of His Life, the Playboy Founder Proposed to Barbi on Four Separate Occasions

When Barbi started questioning Hugh and his intentions for their relationship – and his other relationships with the Playmates – he knew that he needed to do everything he could to keep Barbi. While he certainly had intimate affairs with other women, Barbi was his one true love, and he didn’t want to lose her. So, he proposed.

According to the model, Hugh actually asked her to marry him on four separate occasions. She confessed that “The first time he asked me was after I caught him in an affair. I confronted him. He didn’t admit it at first, but it was kind of hard not to. I moved out every time!” For a while, he managed to win her back. But fourth time wasn’t the charm for Hugh Hefner, as, eventually, Barbi had enough.

When She Realized That Hugh Hefner Would Never Remain Faithful to Her, Barbi Ended Their Relationship for Good

When Barbi’s singing career took off and she began to tour around the country, performing to the masses, the troubles in their relationship got worse. Not only did they have distance between them, but Hugh just couldn’t seem to stay faithful. He would cheat on her time after time, and Barbi didn’t want someone who couldn’t commit wholeheartedly to her.

While Hefner maintained until the day he died that he would always regret cheating on Barbi and not marrying her, the model eventually had to make the decision to leave him. She wanted a proper relationship, and she wanted to live a normal life. She had experienced life in the limelight, and while it provided her with some real highs, she craved the life she had planned for herself when she wanted to be a veterinarian.

What Barbi Didn’t Realize Was That Another Man Was Already Waiting to Date Her As Soon as She Became Available

After almost a decade together, Barbi Benton broke up with Hugh Hefner in 1976. While she was relieved to be free of his infidelities, the breakup hit her hard. She had loved Hugh dearly – but she knew that, ultimately, he wasn’t the right person for her. He was too famous, he was too desirable, and he was too rich. She wanted a simpler life.

But what Barbi didn’t realize was that there was a real estate developer and financial advisor by the name of George Gradow who was looking for a woman just like Barbi Benton. In fact, when his former boss Liz Prince asked George when he was going to get married, he replied with “When I find someone who looks like Barbi Benton.” Amazingly, Liz Prince had the connection to Barbi that George needed…

Real Estate Developer George Gradow Wanted to Date Barbi, and Would Do Everything He Could to Be With Her

As soon as George learned that his boss knew Barbi Benton’s mom, he pushed Liz Price to set her up with her – or at least just get her phone number. He was smitten with her and had been since he saw her on television years ago, and he wanted nothing more than to date her.

However, Barbi was experimenting with her life after Hugh Hefner, and she was casually dating the actor Andrew Prine when a meet-up was arranged between herself and George. In fact, Barbi didn’t even know that George wanted it to be a date, as she thought she was just meeting a financial advisor who specialized in real estate.

Barbi and George Eventually Fell in Love, and They Became Husband and Wife in 1979

However, Barbi’s fling with Andrew Prine was just a fling – and when that ended George amped up his attempts to win her over. George was different from Hugh and Benton could tell that he only had eyes for her. This, coupled with the fact that they had so much in common, meant that they fell in love shortly after they started dating.

In 1979, the couple solidified their love even further when they got married and became husband and wife. Although this was a serious life change for Benton after a life in the limelight, she was more than willing to swap a bustling Playboy Mansion for a large estate with her husband in Pasadena. It felt natural to her.

When the Couple Started a Family, Barbi Began to Question Her Place in the World of Fame and Fortune

Life with George was easy. There were no games, there were no other parties getting involved, and he was just a normal guy. Barbi knew that she wanted to spend the rest of her life with him, and she knew that she wanted to start a family with him. Amazingly, in 1986, the couple welcomed their son, Alexander.

Being a mom gave Barbi a sense of purpose that she had never experienced before, and this feeling became even more intense when they welcomed their daughter Ariana in 1988. Her role as a mother quickly became the most important thing in her life, which is why she started to question her whole career. Should she stay in the limelight? Or should she focus on her children?

In the End, Barbi Decided to Leave the Entertainment World Behind in Favor of a Normal Life With Her Kids

After much deliberation and soul searching, Barbi Benton decided that there wasn’t a place for her in the world of fame and fortune any longer. She had experienced so much already, but her main focus had shifted to her children, and she wanted to give them a normal childhood. So, she decided to retire.

Since then, she’s maintained a normal life outside of the spotlight where she’s devoted her time to raising her kids, spending time with her children, and working as an interior designer. And while Barbi has never left the bright lights of Los Angeles, she now splits her time between the City of Angels and the more calm environment of Aspen, Colorado.

To This Day, Barbi Benton Is Still Considered to Be the Only Woman That Hugh Hefner Has Ever Really Loved

When speaking about Barbi Benton, it’s impossible to avoid the topic of Hugh Hefner. And while Barbi and Hugh had a tumultuous relationship that ultimately ended up with them parting ways, Barbi has confessed that the former couple remained good friends up until his dying day. After all, Hugh needed her in his life.

According to reports of those around him, Barbi Benton is still considered to be the only woman Hugh has ever really loved. And while he had countless relationships with other women and married three times over the course of his life, none of them compared to his one and only. Apparently, letting her leave was one of his biggest regrets.