The Life of Barbi Benton: Hugh Hefner’s One That Got Away

It takes a special woman to tame Hugh Hefner’s wild heart, but Barbara Benton was up to the task. The California-based model dated the Playboy mogul for nearly nine years. She’s the woman behind the iconic mansion and even though she was the one that got away, she remained one of Hefner’s closest confidantes up until his death. This is the story of how a 16-year-old hopeful veterinarian became a Playboy icon.

She Wanted To Be A Vet

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Benton’s childhood was pretty normal. Her dad was a gynecologist and her mom was an investment counselor. They gave her lessons in various activities, from scuba diving to piano, in order to help her discover her passions. Her passion happened to be animals – at least until it wasn’t.

Benton went to UCLA to become a veterinarian but didn’t last long before signing to a commercial agency as a model. “I had to give up [being a vet] when I realized I couldn’t stand the sight of blood,” she said. Her time shooting TV commercials eventually led her to Hugh Hefner, the Playboy model, and her future longterm love.

She was a Teenage Model

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Barbi Benton started modeling when she was 16-years-old and continued racking up credits while attending UCLA. In 1968, Benton landed a role as an extra on Hugh Hefner’s TV show Playboy After Dark. Hefner noticed her studying in-between takes and introduced himself.

“He came up to ask me what I was so diligently working on,” she said. “I told him I was studying for school. He liked the fact that I was a 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.”

She Almost Shut Hef Down

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Benton was just an extra on his show, but Hef was so taken by her that he eventually promoted her to host. Apparently, that’s one of the perks of having a media mogul totally smitten. Surprisingly, she nearly rejected him before he had a chance fall in love.

On the second day of filming, the then-42-year-old Playboy mogul asked 18-year-old Benton on a date and she hesitated because of their 24-year age difference. Initially, she told him, “I don’t know, I’ve never dated anyone over 24 before.” Hef replied “That’s all right, neither have I.”

Their First Date Was at an LA Disco

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On the edge of the ’70s, it makes sense that Benton’s first date with Hef was at a disco. She admitted that Hef asked her out again and again, but she already had her choice of three suitors: her college boyfriend, Golden Globe-nominated actor Jimmy Caan, and the Playboy mogul.

Benton only agreed to go to the disco because it was a group date that included famed author Shel Silverstein. She was a major fan of his work. Hef ended up winning her heart, however, and they began a whirlwind romance packed with celebrity appearances and Hollywood excess.

The Real Reason Behind Her Name Change Is Up For Debate

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Benton was originally born Barbara Klein, but changed her name to the iconic Barbara Benton before achieving mass fame. The reason for the name change isn’t totally clear. While some say Hugh Hefner convinced the star to adopt a more marketable name, it may have actually happened when she landed a roll in the 1969 German film What’s a Nice Girl Like You Doing in a Business like This?

According to People, producers on the film wanted the actress to have a more American-sounding name. She adopted the famous stage name and never looked back.

Barbi Was A Playboy Cover Star Four Times

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Barbie landed her first Playboy cover in July 1969. She went on to appear on the cover three more times: March 1970, May 1972, and December 1985 (after she’d already split from Hef.) She also appeared in two nude spreads in 1973 and 1975.

“I was shy and would make the photographer turn his back when I changed poses,” she told People about her first nude shoot. “By the second one, I just let it all hang out.” Though Benton was indeed one of the Hugh Hefner’s most lasting loves, she never actually ended up becoming Playmate of the Month.

She Found The Playboy Mansion

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The Playboy mansion is an American icon, and you can thank Barbi Benton for the fact that it even exists. Benton is largely credited for finding the mansion and convincing Hef to check it out.

Benton haphazardly stumbled upon its locked-up glory and convinced her Playboy mogul boyfriend to hop on a plane and view it. She later enlisted her mom as the realtor, who ended up doing the deal as a gift to Hef and never took a commission. Hef’s only stipulation for moving into his place was that Benton would come with him. They ended up living together in the mansion for almost nine years.

Hef Proposed To Benton – And Was Rejected — Four Times

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Benton told People that Hef ended up proposing to her quite early on in their relationship. She denied him all four times he asked. The first time was off the heels of an affair that had her temporarily move out of the mansion.

“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,” she said, adding, “The first three were early on, and the fourth was after I was already married. We love each other. I will love him forever.”

Hee Haw Was One Of Benton’s First Reoccurring Roles

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In 1972, Benton landed one of her first reoccurring acting roles in the variety series Hee Haw. The actress performed in various comedy sketches but left after four seasons to become a bonafide Hollywood star (there’s only so much fame you can get with a few Playboy covers and TV sketches.)

Hee Haw was set in the fictional rural town of Kornfield Kounty and aired for over a decade on CBS. Here, Benton got to explore her singing talent as the show was hosted by country music artists Buck Owens and Roy Clark.

Hello, Hollywood Squares

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By the time Benton left Hee Haw, she was already a sketch comedy icon. Late night TV was like a brand new routine. She appeared on The David Frost Show in 1970 and American Bandstand and The Norman Gunston Show in 1975. She even performed on the iconic Sonny and Cher Show in 1977.

Throughout the mid-1970s and early ’80s, Benton was a reoccurring guest on The Tonight Show Starring Johnny Carson. As a singer and actress, she appeared on The Mike Douglas Show between 1973 and 1980. In 1978, she found herself as a panelist on the iconic game show The Hollywood Squares. She found great success with the series and reappeared in Match Game/Hollywood Squares Hour in 1983 (the same year she made her final cameo on Hee Haw because the girl never forgot her roots.)

It’s Sugar Time!

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Sugar Time! isn’t exactly one of those iconic 1970s series that people remember fondly. It wasn’t The Brady Bunch or Love Boat. In fact, despite its moderate ratings (6.1 out of 10 on IMDb) it would appear that hardly anyone watched the show at all.

Sugar Time followed the story of all-female rock trio and enlisted Barbi Benton as its lead, a hatcheck girl named Maxx Douglas. The actress got to show off her singing chops alongside Marianne Black and Didi Carr, who played Benton’s bandmates in Sugar. Unfortunately, two seasons and 13 episodes later, the series was cancelled.

She Dumped Hefner For Good In 1976

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Hugh Hefner was known as the ultimate Playboy for a reason (and it’s not just because he founded the magazine.) Anyone who’s ever seen The Girls Next Door knows that Hefner had some issues with remaining monogamous. They eventually ruined his relationship with reality star and Playboy model Holly Madison like they tarnished his relationship with Benton.

“One of the problems is I became a successful singer, and I was on tour much too much,” she told People about their breakup. “He just couldn’t be faithful that long. The more successful I became, the harder it was. It was hard on our relationship. And when you’re hurt, it’s not a good time to ask someone to marry them. It was his way of him getting me to come back. Because I moved out every time. By the third time, I moved out for good.”

Hef Regretted Not Getting Married

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According to The Daily Mail, Benton and Hef dated from 1968 to 1976, but never got married. In fact, it was one of Hef’s biggest regrets and ultimately the reason Benton decided to move on.

“I only regret not marrying Barbi,” says Hugh, “because it finally led to our going separate ways. But I have been married and have children and wasn’t, and am not, interested in doing it again. Barbi hadn’t had that and wanted it.” Despite their split, the pair remained great friends and Benton regularly appeared on the E! reality series Girls Next Door.

Barbi Hung Out With Bill Cosby

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Shortly after Benton and Hef moved into the Playboy mansion, the pair started throwing extravagant parties. One of the frequent guests was actor Bill Cosby, who was just starting to build TV fame with I Spy. At the time, Cosby’s wife Camille was pregnant with her son Ennis and the pair had two children at home.

Benton never heard about any of Cosby’s numerous sexual assault allegations while he was a mansion guest, though ex-Bunny PJ Masten claimed he molested 13 former Playboy bunnies.

She did notice one thing…

Benton Did Notice One Thing

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Although she didn’t know of his reputation at the time, Benton did notice Cosby habitually cheated on his wife with Paige Young, 1968’s Playmate of the Month.

“I’ve followed all these recent stories and I have seen the YouTube videos of girls coming forward and they seem to be legitimate,” Benton told The Daily Mail about Cosby’s allegations, “So I really don’t know what to say.” She also claimed Hef would have banned Cosby from the mansion had he known.

Barbi Doll Became A Hit

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By the mid-1970s, Benton already had flexed her country-singing muscles with Hee Haw. She ended up releasing her first album as a country singer in 1975. Her debut album Barbi Doll peaked at No. 17 on the US Country charts. The single “Brass Buckles” climbed the Billboard country singles charts until it landed in the Top 5.

Benton continued releasing music on Playboy Records, but never saw the same success. She released Barbi Benton the same year as her debut and it peaked at No. 18. Her 1976 release Something New peaked at No. 39 and her 1978 release Ain’t That Just The Way failed to chart in the US. Thankfully, she had a different approach to success.

Aint That Just The Way

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Aint That Just The Way never ended up charting in the US, but that didn’t mean it failed to achieve international success. The eponymous single was a No. 1 hit in Sweden for five weeks. In 1977, it was re-recorded by Dutch singer and fellow Playboy model Patricia Paay under the name “Poor Jeremy,” then it resurfaced in 1996 when Lutricia McNeil climbed the charts with her cover.

Benton wasn’t just a model, she was in charge of her musical career. The singer composed her own songs and self-produced her last album. Kinetic Voyage, her 1988 LP, was the only release not on Playboy Records. It was her last.

She Met George Gradow Thanks To Mom

She Met George Gradow Thanks To Mom

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After Benton called it quits with Hef, she fell into the arms of George Gradow. Their relationship came about in the way few Hollywood relationships do – a meeting set-up by mom. Gradow famously told his employee Liz Prince that he’d only get married if he found someone who looked like Barbi Benton. Prince happened to know Benton’s mother and set up a meeting.

Originally, Benton viewed Gradow as a financial adviser and businessman. She was seeing actor Andrew Prince at the time, but when that fizzled, she invited the tycoon to the Academy of Country Music Dinner. He proposed after four months.

She Traded Her Mansion Keys for a Pasadena Palace

She Traded Her Mansion Keys for a Pasadena Palace

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Benton married entrepreneur George Gradow in 1979. When she moved out of the Playboy mansion, she traded her lavish lifestyle for something equally as impressive. Benton and Gradow shared a 28-room mansion with an indoor swimming pool. Each room was more opulent than the next with exotic wood flooring and hand-picked amethyst, quartz, and pyrite. If you can picture it, it’s even more outlandish than the Playboy mansion.

Benton enlisted 40 artists to help craft her dream home, but she designed the interior herself. “We’d bring in other designers, and George would go, ‘Zzzz—you can do that in your sleep,’” Benton said. “George has no idea how to decorate till he sees it firsthand. Then he’d say, ‘I like it—but I want it wilder.’ So that’s what I’d try to give him.”

Her Last Visit To Hef Was Heartbreaking

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Benton last saw Hugh Hefner about six months before he passed away. They both shared a nostalgic moment in the playboy mansion and the star opened up about her experience to People.

“I went up to the Mansion, and rather than sit where other people were, he wanted to sit with me privately. When I was there for a party or a small get-together, I never got to talk to Hef. So we went to one of the rooms in the Mansion, and behind closed doors, we had the most amazing conversation about old times,” she said. “We just had a great talk. I felt like he kind of knew that it was coming to an end. When I left, he said, ‘I hope you come up and see me more often.’”

She Claimed The Playboy Mogul Though He Had Plenty Of Time Left

She Claimed The Playboy Mogul Though He Had Plenty Of Time Left

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Though Benton admitted that Hefner’s memory was “fading” and the star was in “poor health,” she also claimed Hefner though he had a lot of time left. No one really expected him to pass away as quickly as he did (though, he definitely lived a life longer than most.)

“He didn’t think he was going to die anytime in the immediate future,” she told People. “He was upset [with reports] that said he didn’t have much time left. He said, ‘I have plenty of time left! I’m not going anywhere just yet.’”