Hugh Hefner Pictures - Gallery Page 4

Strikeforce, held at the Playboy Mansion - Los Angeles, California - Saturday 29th September 2007

Holly Madison, Hugh Hefner and Playboy
Hugh Hefner and Playboy
Holly Madison, Hugh Hefner and Playboy
Hugh Hefner and Playboy

Black Card Party held at Vice - Los Angeles, California - Thursday 13th September 2007

Kendra Wilkinson, Holly Madison and Hugh Hefner
Holly Madison and Hugh Hefner
Holly Madison and Hugh Hefner
Kendra Wilkinson, Holly Madison and Hugh Hefner

The Sports Dream Celebrity Poker Tournament at the Playboy Mansion - Los Angeles, California - Tuesday 10th July 2007

Hugh Hefner
Hugh Hefner

The season finale of 'The Girls Next Door' at the Renaissance Pleasure Faire - California, USA - Saturday 12th May 2007

Hugh Hefner
Hugh Hefner
Hugh Hefner
Hugh Hefner
Hugh Hefner

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Hugh Hefner and Crystal Hefner - Hugh Hefner and Crystal Hefner ride mobility scooters through Disneyland Park - Anaheim, CA,...

Hugh Hefner at Disneyland

Hugh Hefner and Crystal Hefner - Hugh Hefner and Crystal Hefner ride mobility scooters through Disneyland Park - Anaheim, CA,...

Hugh Hefner - Playboy Magazine's 2013 Playmate of the Year ceremony held at the Playboy Mansion. - Holmy Hills, California,...

Playmate of the Year

Hugh Hefner - Playboy Magazine's 2013 Playmate of the Year ceremony held at the Playboy Mansion. - Holmy Hills, California,...

Hugh Hefner 2012 MusiCares Person Of the Year Gala Honoring Paul McCartney held at the Los Angeles Convention Center Los...

Hugh Hefner 2012 MusiCares Person Of the Year Gala Honoring Paul McCartney held at the Los Angeles Convention Center Los...

Hugh Hefner, guest,  at 'The Rum Diary' premiere held at the LACMA Bing Theater - Arrivals Los Angeles, California...

Hugh Hefner, guest, at 'The Rum Diary' premiere held at the LACMA Bing Theater - Arrivals Los Angeles, California...

Hugh Hefner The 6th Annual Kandyland Party at the Playboy Mansion Beverly Hills Los Angeles, California - 25.06.11

Hugh Hefner The 6th Annual Kandyland Party at the Playboy Mansion Beverly Hills Los Angeles, California - 25.06.11

Hugh Hefner with fiancee Crystal Harris (Centre R) Playboy Club London Gala Opening Event held at the Playboy Club in...

Hugh Hefner with fiancee Crystal Harris (Centre R) Playboy Club London Gala Opening Event held at the Playboy Club in...

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Hugh Hefner with wife Crystal Harris Playboy Club London Gala Opening Event held at the Playboy Club in Mayfair -...

Hugh Hefner with wife Crystal Harris Playboy Club London Gala Opening Event held at the Playboy Club in Mayfair -...

Hugh Hefner, Crystal Harris  Playboy's Playmate of the Year 2011 at Moon Nightclub at The Palms Hotel and Casino...

Hugh Hefner, Crystal Harris Playboy's Playmate of the Year 2011 at Moon Nightclub at The Palms Hotel and Casino...

Claire Sinclair and Hugh Hefner Playboys Playmate of the Year 2011 at Moon Nightclub at The Palms Hotel and Casino...

Claire Sinclair and Hugh Hefner Playboys Playmate of the Year 2011 at Moon Nightclub at The Palms Hotel and Casino...

Hugh Hefner riding a mobility scooter whilst enjoying a day out at Disneyland  Los Angeles, California - 21.04.11

Hugh Hefner riding a mobility scooter whilst enjoying a day out at Disneyland Los Angeles, California - 21.04.11

Hugh Hefner, Marston Hefner, Claire Sinclair and Playboy Playmates Playboy Founder and legend Hugh Hefner and son Marston Hefner celebrate...

Hugh Hefner, Marston Hefner, Claire Sinclair and Playboy Playmates Playboy Founder and legend Hugh Hefner and son Marston Hefner celebrate...

Hugh Hefner celebrates the New Year with his fiance Crystal Harris in a picture posted on Plixi.com USA - 31.12.10

Hugh Hefner celebrates the New Year with his fiance Crystal Harris in a picture posted on Plixi.com USA - 31.12.10

Hugh Hefner and Crystal Harris Playboy Playmate Claire Sinclair guest stars at The Crazy Horse Paris at the MGM Grand...

Hugh Hefner and Crystal Harris Playboy Playmate Claire Sinclair guest stars at The Crazy Horse Paris at the MGM Grand...

Anna Berglund, Hugh Hefner and Crystal Harris Hugh Hefner hosts a Special Evening at The Playboy Club at The Palms...

Anna Berglund, Hugh Hefner and Crystal Harris Hugh Hefner hosts a Special Evening at The Playboy Club at The Palms...

Hugh Hefner and Hope Dworaczyk 2010 Playmate of The Year announcement at The Palms Hotel & Casino  Las Vegas,...

Hugh Hefner and Hope Dworaczyk 2010 Playmate of The Year announcement at The Palms Hotel & Casino Las Vegas,...

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Hugh Hefner Celebrities arrive at the Staples Center to watch the Los Angeles Lakers play Oklahoma City Los Angeles, California...

Hugh Hefner Celebrities arrive at the Staples Center to watch the Los Angeles Lakers play Oklahoma City Los Angeles, California...

Hugh Hefner 2009 Fox Reality Channel Really Awards held at The Music Box - Arrivals Los Angeles, California - 13.10.09

Hugh Hefner 2009 Fox Reality Channel Really Awards held at The Music Box - Arrivals Los Angeles, California - 13.10.09

Hugh Hefner and Crystal Harris Joined by Crystal Harris and some Playboy Playmates, Hugh Hefner and twins Karissa and Kristina...

Hugh Hefner and Crystal Harris Joined by Crystal Harris and some Playboy Playmates, Hugh Hefner and twins Karissa and Kristina...

Hugh Hefner's twin girlfriends Karissa Shannon and Kristina Shannon attend a signing session for 'Playboy's Miss July and Miss August'...

Hugh Hefner's twin girlfriends Karissa Shannon and Kristina Shannon attend a signing session for 'Playboy's Miss July and Miss August'...

Hugh Hefner and Playmates Celebrities arrive to watch the Los Angeles Lakers game against the Denver Nuggets at the Staples...

Hugh Hefner and Playmates Celebrities arrive to watch the Los Angeles Lakers game against the Denver Nuggets at the Staples...

Hugh Hefner Playboy Playmate of The Year 2009 held at The Palms Hotel Casino - Arrivals Las Vegas, Nevada -...

Hugh Hefner Playboy Playmate of The Year 2009 held at The Palms Hotel Casino - Arrivals Las Vegas, Nevada -...

Hugh Hefner and Ida Ljungqvist Playboy Playmate of The Year 2009 held at The Palms Hotel Casino Las Vegas, Nevada...

Hugh Hefner and Ida Ljungqvist Playboy Playmate of The Year 2009 held at The Palms Hotel Casino Las Vegas, Nevada...

Hugh Hefner and Crystal Harris The launch of Lengths for Love charity at The Highlands Hollywood, California - 14.02.09

Hugh Hefner and Crystal Harris The launch of Lengths for Love charity at The Highlands Hollywood, California - 14.02.09

Hugh Hefner and Crystal Harris Aubrey O'Day celebrates her birthday and the release of the March 2009 issue of Playboy...

Hugh Hefner and Crystal Harris Aubrey O'Day celebrates her birthday and the release of the March 2009 issue of Playboy...

Hugh Hefner 2nd Annual Leather Meets Lace event to benefit Jenny McCarthy's charity Generation Rescue held at the Playboy Mansion...

Hugh Hefner 2nd Annual Leather Meets Lace event to benefit Jenny McCarthy's charity Generation Rescue held at the Playboy Mansion...

Hugh Hefner with playboy models leaving STK restaurant in West Hollywood with a film crew, recording TV programme 'The Girls...

Hugh Hefner with playboy models leaving STK restaurant in West Hollywood with a film crew, recording TV programme 'The Girls...

Hugh Hefner and Holly Madison 3rd Annual Celebrity Poker Tournament and Casino Night at the Playboy Mansion Los Angeles, California...

Hugh Hefner and Holly Madison 3rd Annual Celebrity Poker Tournament and Casino Night at the Playboy Mansion Los Angeles, California...

Hugh Hefner and Holly Madison Playboy announces Jayde Nicole as Playboy's 2008 Playmate of the Year at a luncheon at...

Hugh Hefner and Holly Madison Playboy announces Jayde Nicole as Playboy's 2008 Playmate of the Year at a luncheon at...

Hugh Hefner signs copies of 'Playboy Cover To Cover: The 50s' at Banes & Noble in The Grove Los Angeles,...

Hugh Hefner signs copies of 'Playboy Cover To Cover: The 50s' at Banes & Noble in The Grove Los Angeles,...

Hugh Hefner Strikeforce, held at the Playboy Mansion Los Angeles, California - 29.09.07

Hugh Hefner Strikeforce, held at the Playboy Mansion Los Angeles, California - 29.09.07

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