He lived life like there was no tomorrow, and on September 27, 2017, Playboy mogul,
Hugh Marston Hefner passed on to the grotto in the sky.
Hef's reputation as a ladies man preceded him, and the older he got, the more women
he dated.
Here's what some of those ladies look like today.
Barbi Benton
Barbara Lynn Klein wanted to be a veterinarian but, quote, "couldn't stand the sight of blood."
Instead, she set her sights on the entertainment industry.
In 1968, at age 18, Klein landed a role on the Playboy After Dark TV show working alongside
Hefner himself.
Klein said, "I told him I never dated a man over 24...He told me he never dated anyone
older than that either."
Hefner convinced her to change her name to Barbi Benton and move into the Playboy Mansion.
After ending their eight-year relationship, Benton then launched a short-lived career
as a country singer in the '70s and was best known for the track "Brass Buckles."
Lillian Müller
Hefner was still with Benton when he met the captivating Lillian Müller, the Norwegian
beauty who landed Playmate of the Year in 1976.
After catching Hefner's eye, Müller moved into the mansion.
She then went on to star in music videos for Van Halen and Rod Stewart.
These days, she's an outspoken advocate for healthy eating and wellness.
Kimberley Conrad
Hefner tied the knot for the second time in 1989, with Kimberly Conrad — an Alabama
girl who made her glossy debut in January 1988.
In '89, she was crowned Playmate of the Year.
She remembered, "Hef and I started dating, got married, had kids, and the rest is history...
The 54-year-old recreated one of her iconic '80s covers in July 2017.
The Bentley twins
Sandy and Mandy Bentley were two Catholic girls from Chicago who Hefner met briefly
at the Hollywood hot spot known as the Garden of Eden.
Hef told Rolling Stone, "The night I met them, I said, 'You girls dropped from heaven.'"
As Hef tells it, all it took was a few phone calls, and the Bentley twins were living it
up at the mansion.
The girls made cameo appearances in S--and the City and Two and a Half Men, before moving
on to other wealthy boyfriends.
Brande Roderick
The Bentley twins were joined in bed by Baywatch star, Brande Roderick, who appeared in the
magazine in April 2000, and was named 2001's Playmate of the Year.
Roderick said of the Bentley twins, "We all love each other...We're like a family.”
Post-bunny, Roderick landed minor film roles in The Nanny Diaries and Starsky and Hutch.
Tina Marie Jordan
Hollywood native Tina Marie Jordan was transitioning into real estate when she met Hefner at Garden
of Eden, one of his regular haunts.
Soon after Jordan moved into the mansion, she was featured as Miss March 2002.
She said, "Hef just wants to have a good time and be happy...He's a warm and generous person,
a family man who cares a great deal about me and my three-year-old daughter."
These days, Jordan's perhaps best-known for her selfie-laden Instagram feed.
Bridget Marquardt
Bridget Marquardt was one of the stars of The Girls Next Door and one of Hefner's three
girlfriends at the time the show began.
At 31, she was the oldest of his partners.
She moved out after three years, after falling for cinematographer Nicholas Carpenter.
Just months before Hefner's passing, she told Australia's The Morning Show, "He told me
there was always an open door… but I heard that that's not quite true lately."
Holly Madison
Another star of The Girls Next Door, Holly Madison, was discovered by Hefner's scouts
while working as a Hooters girl.
"After Hef's and my first date I moved in two days later.
I guess you could say we were made for each other."
The Oregon-born theater-major moved into the mansion just in time to land a spot on the
reality series, in 2001.
By the time her seven-year relationship with Hefner came to an end, she had enough star
power to front her own show, Holly's World, from 2009 to 2011.
In July 2015, Madison made The New York Times best-seller list with Down the Rabbit Hole,
in which, she revealed the reason she left Hefner, writing, "I learned Hef was the manipulator
and that he pitted us against one another...I realized I wasn't treated well…I don't have
any loyalty to Hef."
These days, Madison's keeping up with her lifestyle brand, and raising two beautiful
kids.
Kendra Wilkinson
The last of the original Girls Next Door, Kendra Wilkinson, was working as a dental
assistant when she scored a gig at Hefner's 78th birthday bash.
Within a matter of days, she moved into the mansion to live with Hef, Madison, and Marquardt.
"Dave and Buster's is actually a very special place to me and Hef because that was the place
where Hef called me and asked me to move in."
Five years later, Wilkinson moved out on good terms.
She even held her wedding with former pro football star Hank Baskett at the mansion
in June 2009.
She told E! News she's open about her past, saying, "It starts now with teaching [my family]
who I am...They've been up to the Playboy Mansion.
I have nothing to hide."
Kristina and Karissa Shannon
Twins Kristina and Karissa Shannon landed in the finals of the 55th Anniversary Playmate
Search.
Hef then offered the girls a joint centerfold shoot and invited them to live at the mansion
as his new girlfriends.
The twins' residency at the mansion ended in 2010, and things haven't been going great
for them since.
The pair was involved in a car accident that reportedly led to Kristina getting slapped
with a DUI in 2015.
Crystal Harris Hefner
When Crystal Harris attended a Halloween party at the mansion in 2008, she had no idea she
would end up becoming Hef's third and final wife.
Harris appeared as Miss December 2009, and Hef popped the question the next year.
The two made it official in a private ceremony in December 2012.
Following his passing, Harris told Us Weekly, "I am heartbroken…
I will feel eternally grateful to have been by his side, holding his hand, and telling
him how much I love him."
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