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Ex Playboy model Karen McDougal shares suggestive hot tub photo
Ex Playboy model Karen McDougal shares suggestive hot tub photo
His mother worked for Playboy, dad is a rocker. Who is he?
His mother worked for Playboy, dad is a rocker. Who is he?
Trump Playboy model didn't want to be next Monica Lewinsky
Trump Playboy model didn't want to be next Monica Lewinsky
Playboy rabbi who hired two hitmen to kill wife found dead in prison
Playboy rabbi who hired two hitmen to kill wife found dead in prison
Ex-Playboy model cleared to testify in Trump hush money trial
Ex-Playboy model cleared to testify in Trump hush money trial
Playboy model says golden rule is never having sex on first date
Playboy model says golden rule is never having sex on first date
Former porn star who was raised a strict Christian poses for Playboy
Former porn star who was raised a strict Christian poses for Playboy
Playboy model is charged with offering federal agent $5,000 bribe
Playboy model is charged with offering federal agent $5,000 bribe
Jenny McCarthy says there was 'sex going on' at the Playboy mansion
Jenny McCarthy says there was 'sex going on' at the Playboy mansion
Leonardo DiCaprio's 'three word response' to Playboy model, 22
Leonardo DiCaprio's 'three word response' to Playboy model, 22
Playboy model calls Leonardo DiCaprio 'weird & old' after kissing him
Playboy model calls Leonardo DiCaprio 'weird & old' after kissing him
Playboy model says Justin Timberlake cheated on Cameron Diaz with her
Playboy model says Justin Timberlake cheated on Cameron Diaz with her
German princess becomes first aristocrat to appear naked in Playboy
German princess becomes first aristocrat to appear naked in Playboy
Playboy model Masuimi Max is dead at 45
Playboy model Masuimi Max is dead at 45
My life with the ultimate Playboy: Exclusive with CRYSTAL HEFNER
My life with the ultimate Playboy: Exclusive with CRYSTAL HEFNER
Playboy founder Hugh Hefner's famous smoking jacket ensemble for sale
Playboy founder Hugh Hefner's famous smoking jacket ensemble for sale
Infamous former Playboy Bunny Carole Gold is RELEASED from jail early
Infamous former Playboy Bunny Carole Gold is RELEASED from jail early
Hugh Hefner's wife Crystal shares her Playboy-themed Christmas decor
Hugh Hefner's wife Crystal shares her Playboy-themed Christmas decor
Hugh Hefner's wife Crystal shares her Playboy-themed Christmas decor
Hugh Hefner's wife Crystal shares her Playboy-themed Christmas decor
Hugh Hefner's wife Crystal shares her Playboy-themed Christmas decor
Hugh Hefner's wife Crystal shares her Playboy-themed Christmas decor
Hugh Hefner's wife Crystal shares her Playboy-themed Christmas decor
Hugh Hefner's wife Crystal shares her Playboy-themed Christmas decor
His true love was cocaine: The Crown depicts Dodi Fayed as a playboy
His true love was cocaine: The Crown depicts Dodi Fayed as a playboy
Playboy Mansion renovation contnues six years after Hefner's death
Playboy Mansion renovation contnues six years after Hefner's death
Model voted Playboy's 'perfect woman' spent $300K on plastic surgery
Model voted Playboy's 'perfect woman' spent $300K on plastic surgery
EXCL: Playboy model Madisyn Shipman teases MLB star romance
EXCL: Playboy model Madisyn Shipman teases MLB star romance
Playboy fires Mia Khalifa after pornstar mocked slaughter of Jews
Playboy fires Mia Khalifa after pornstar mocked slaughter of Jews
Former child stars who have shed wholesome image for PORN and Playboy
Former child stars who have shed wholesome image for PORN and Playboy
Former Nickelodeon child star joins Playboy after feeling 'repressed'
Former Nickelodeon child star joins Playboy after feeling 'repressed'
Lisa Lyon, bodybuilding pioneer and playboy model, dies at 70
Lisa Lyon, bodybuilding pioneer and playboy model, dies at 70
Bodybuilding pioneer and playboy model Lisa Lyon 'in grave condition'
Bodybuilding pioneer and playboy model Lisa Lyon 'in grave condition'
The hell of living with Hugh Hefner by his playboy bunny
The hell of living with Hugh Hefner by his playboy bunny
Injured Ukrainian mother appears on the cover of Playboy
Injured Ukrainian mother appears on the cover of Playboy
Drake fan hired by Playboy reveals star has DMed her to offer advice
Drake fan hired by Playboy reveals star has DMed her to offer advice
Mom who threw 36G bra at Drake has now been contacted by Playboy
Mom who threw 36G bra at Drake has now been contacted by Playboy
Pamela Anderson inspires hundreds of submissions for Playboy contest
Pamela Anderson inspires hundreds of submissions for Playboy contest
Germany women's star 'turns down a naked cover shoot with Playboy'
Germany women's star 'turns down a naked cover shoot with Playboy'
Hugh Hefner's wife Crystal is set to lift lid on Playboy mansion
Hugh Hefner's wife Crystal is set to lift lid on Playboy mansion
How Alex Soros revamped playboy image to beat brother to father's $25B
How Alex Soros revamped playboy image to beat brother to father's $25B
Outrage over bikini runway show fronted by Playboy model
Outrage over bikini runway show fronted by Playboy model
Claudia Conway joins Playboy.com as a 'bunny', sharing racy photos
Claudia Conway joins Playboy.com as a 'bunny', sharing racy photos
Martha Stewart, 81, rules out Playboy after Sports Illustrated cover
Martha Stewart, 81, rules out Playboy after Sports Illustrated cover
Former Playboy model turned Italian princess is EVICTED from castle
Former Playboy model turned Italian princess is EVICTED from castle
Playboy model slams Hollywood writers for 'ruining television'
Playboy model slams Hollywood writers for 'ruining television'
Playboy butler says girls asked him to take pics to avoid 'creeps''
Playboy butler says girls asked him to take pics to avoid 'creeps''
Stephen Wayda lifts lid on iconic Playboy shoots
Stephen Wayda lifts lid on iconic Playboy shoots
Texan heiress posed for Playboy to get back at cheating Dem husband
Texan heiress posed for Playboy to get back at cheating Dem husband
Playboy model-turned-Italian princess EVICTED from $533m Roman villa
Playboy model-turned-Italian princess EVICTED from $533m Roman villa
Anna Nicole Smith: You Don't Know Me trailer shows Playboy pin-up
Anna Nicole Smith: You Don't Know Me trailer shows Playboy pin-up
Trump grand jury probes SECOND 'hush-money' payment to Playboy model
Trump grand jury probes SECOND 'hush-money' payment to Playboy model