Hugh Hefner's wives and girlfriends through the years (Photos)

Hugh Hefner passed away Wednesday at 91-years-old and he sure did live a life fit for the founder of Playboy Enterprises.

Here are some of the wives and girlfriends of Hefner’s past.

Mildred Williams (1949-1959)

Hefner met Mildred Williams in college and they got married in 1949. The pair had two kids together. Williams had revealed that she had an affair while Hefner was serving in the army. He’s said: “That was the most devastating moment in my life.”

According to Hefner, his wife would let him sleep with other women to make up for her infidelity.

The two divorced in 1959.

Barbi Benton (1969-1976)

15 PHOTOS
Hugh Hefner and Barbi Benton together
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Hugh Hefner and Barbi Benton together
NEW YORK, NY - CIRCA 1970s: Barbi Benton and Hugh Hefner at the Playboy Club circa 1970s in New York City. (Photo by PL Gould/IMAGES/Getty Images)
Hugh Hefner and his girlfriend Barbi Benton visit his Playboy Club in London. (Photo by � Hulton-Deutsch Collection/CORBIS/Corbis via Getty Images)
Playboy CEO Hugh Hefner with partner model, actress and singer Barbara Benton arrive at Paris Airport. (Photo by James Andanson/Sygma via Getty Images)
American magazine publisher Hugh Hefner and his companion, American model and actor Barbi Benton, relax on a bed while a stewardess attends to them in the private quarters of Hefner's DC-9 jetliner, 'The Big Bunny' en route to Heathrow. (Photo by Hulton Archive/Getty Images)
EXCLUSIVE American publishing mogul Hugh Hefner smiles with his companion, American actor Barbi Benton, as they attend the Academy Awards at the Dorothy Chandler Pavilion, Los Angeles, California. Hefner holds a pipe and wears a velvet suit with a matching bow tie and a ruffled tuxedo shirt. (Photo by Gene Lester/Getty Images)
Playboy magazine editor Hugh Hefner is accompanied by Barbi Benton at the 1970 Academy Awards.
American publisher Hugh Hefner and his girlfriend, Playboy model Barbi Benton, in his aircraft at London Airport, before flying back to Chicago, 20th February 1971. (Photo by Dove/Daily Express/Getty Images)
8th March 1971: American magazine publisher Hugh Hefner, holding a pipe, and his companion, American model and actor Barbi Benton, attend a fight between Muhammad Ali and Joe Frazier, New York City. (Photo by Santi Visalli Inc./Getty Images)
Hugh Hefner and Barbi Benton during Warren Cowan's Wedding at Home of Warren Cowan in Beverly Hills, California, United States. (Photo by Ron Galella/WireImage)
American publisher Hugh Hefner, of Playboy Enterprises, smiles with his girlfriend, American actor and model Barbi Benton as they attend the 21st annual SHARE fund raiser for The Exceptional Children's Foundation. She wears a feathered blouse and he holds a pipe. (Photo by Frank Edwards/Getty Images)
LOS ANGELES,CA - APRIL 2,1974: Hugh Hefner with Playmate Barbi Benton arrives to the 46th Academy Awards at Dorothy Chandler Pavilion in Los Angeles,California. (Photo by Michael Montfort/Michael Ochs Archives/Getty Images)
WALTHAM, MA - MAY 19: Playboy magazine founder Hugh Hefner and his girlfriend Barbi Benton are pictured at the Brandeis University commencement in Waltham, MA on May 19, 1974. (Photo by Don Preston/The Boston Globe via Getty Images)
378119 01: 7/17/99 Los Angeles, Ca. Barbi Benton And Hugh Hefner At The Playboy Expo '99 & Playmate Reunion Held At The Pacific Design Center. (Photo By Brad Elterman/Getty Images)
LOS ANGELES, CA - MAY 03: Hugh Hefner and Barbi Benton attend the 2007 Playmate of the Year party at the Playboy Mansion on May 3, 2007 in Los Angeles, California. (Photo by Chad Buchanan/Getty Images)
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She landed a role on “Playboy After Dark” where she met Hugh Hefner. According to People, the two lived together for nine years and Hefner has said “I only regret not marrying Barbi,” said Hefner, “because it finally led to our going separate ways.”

Carrie Leigh (1983-1988)

5 PHOTOS
Hugh Hefner and Carrie Leigh together
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Hugh Hefner and Carrie Leigh together
Carrie Leigh and Hugh Hefner during 'The Natural' Los Angeles Premiere at Samuel Goldwyn Theater in Beverly Hills, California, United States. (Photo by Ron Galella/WireImage)
Hugh Hefner and Carrie Leigh during 2nd Commitment to Life AIDS Project Benefit at Wiltern Theater in Los Angeles, California, United States. (Photo by Ron Galella/WireImage)
Carrie Leigh and Hugh Hefner (Photo by Ron Galella/WireImage)
375250 01: Mid-1980's Playboy Mansion. Hugh Hefner and girlfriend Carrie Leigh at the Playboy Mansion.
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Leigh was Hefner’s live-in girlfriend for five years before she left him and said that being in the mansion was “almost like a cult.”

Kimberley Conrad (1989 – 2010)

13 PHOTOS
Hugh Hefner and Kimberley Conrad together
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Hugh Hefner and Kimberley Conrad together
(Original Caption) 3/9/1988-Los Angeles, California- Hugh Hefner tickles the leg of his latest significant other, Kimberly Conrad, 25, who was Playboy's centerfold, before speaking to reporters at a press conference in Los Angeles. Heffner announced he had filed a counter-suit against his former significant other, Carrie Leigh, accusing her of infidelity.
BEVERLY HILLS, CA - MARCH 10: Hugh Hefner and Kimberley Conrad attend 16th Annual American Film Institute Lifetime Achievement Awards Honoring Jack Lemmon on March 10, 1988 at the Beverly Hilton Hotel in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
BEVERLY HILLS, CA - OCTOBER 19: Hugh Hefner and Kimberley Conrad attend Princess Grace Foundation Gala Honoring Cary Grant on October 19, 1988 at the Beverly Hilton Hotel in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
LOS ANGELES, CA - MAY 23: Hugh Hefner and Kimberley Conrad attend the perofmance of 'Phantom of the Opera' on May 23, 1989 at the Ahmanson Theater in Los Angeles, California. (Photo by Ron Galella, Ltd./WireImage)
American publisher Hugh Hefner with his wife Kimberley Conrad, circa 1990. (Photo by Kypros/Getty Images)
BEVERLY HILLS, CA - DECEMBER 3: Hugh Hefner and Kimberley Conrad attend Society of Singers Gala on December 3, 1990 at the Beverly Hilton Hotel in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
American publisher Hugh Hefner with his wife, Playboy Playmate Kimberley Conrad and their son Marston Hefner at the Playboy Playmate Of The Year Celebration, 25th April 1991. (Photo by Kypros/Getty Images)
BEVERLY HILLS, CA - AUGUST 27: Hugh Hefner, Kimberley Conrad and son Marston Hefner attend Playboy Mansion Open House Party on August 27, 1992 at the Playboy Mansion in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
Hugh Hefner and Kimberley Conrad in Photo Booth (Photo by Frank Trapper/Corbis via Getty Images)
BEVERLY HILLS, CA - APRIL 6: Hugh Hefner and Kimberley Conrad attend Playboy Magazine Party on April 6, 1995 at the Playboy Mansion in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
CENTURY CITY, CA - OCTOBER 9: Hugh Hefner and Kimberley Conrad attend Friar's Club Gala Honoring Hugh Hefner on October 9, 1998 at the Century Plaza Hotel in Century City, California. (Photo by Ron Galella, Ltd./WireImage)
BEL AIR, CALIFORNIA - OCTOBER 18: Hugh Hefner and his former wife Kimberley Conrad Hefner who both accepted Wildlife achievement awards at the 9th annual 'Safari Brunch' at the Playboy Mansion to benefit the Wildlife Waystation, Country's Premier wild Animal Refuge October 18, 2003 in Bel Air, California. (Photo by Frazer Harrison/Getty Images)
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Conrad married Hefner in 1989 and the pair had two children together. Nine years into their marriage, the two separated but remained legally husband and wife. After an 11 year separation, the two filed for divorce.

Mandy and Sandy Bentley (1999-2000)

7 PHOTOS
Hugh Hefner and Mandy and Sandy Bentley together
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Hugh Hefner and Mandy and Sandy Bentley together
E367623 01: (ITALY OUT) Hugh Hefner, center, celebrates the upcoming May issue of Playboy with his girlfriends, cover girls Sandy and Mandy Bentley, April 12, 2000 in New York City. (Photo by Arnaldo Magnani)
Playboy magazine publisher Hugh Hefner accompanied by his playmates: Brande Roderick, Sandy and Mandy Bentley | Location: Paris. (Photo by Jeremy Bembaron/Sygma via Getty Images)
F367591 04: Twin sisters Sandy, left, and Mandy Bentley, right, along with Playboy''s Hugh Hefner, center, pose for a photograph before signing autographs at the Crown Books store in Chicago, Il., April 11, 2000. The twin sisters posed together for the cover of the May issue of Playboy Magazine. (Photo by Tim Boyle)
NEW YORK, UNITED STATES: Playboy Chairman Emeritus and Founder Hugh Hefner (C) is surrounded by his girlfriends Sandy and Mandy Bentley and New York Stock Exchange Chairman Richard Grasso (L) and NYSE President William Johnston (R) before Hefner rang the closing bell at the end of the trading day 13 April, 2000. AFP PHOTO Henny Ray ABRAMS (Photo credit should read HENNY RAY ABRAMS/AFP/Getty Images)
Hugh Hefner with cover girls Sandy Bentley and Mandy Bentley (Photo by RJ Capak/WireImage)
SANTA MONICA, UNITED STATES: Playboy Magazine founder Hugh Hefner (3rd from left) and companions Jessica Paisley (L), Mandy Bentley (2nd L) and Sandy Bentley (R) arrive for the Baywatch 10th Anniversary celebration 02 May, 2000 in Santa Monica, CA. Baywatch is one of the most watched television series in the world. (ELECTRONIC IMAGE) AFP PHOTO/VINCE BUCCI/vb (Photo credit should read Vince Bucci/AFP/Getty Images)
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The twin sisters were Hefner’s first twin live-in girlfriends for a year.

Brande Roderick (2000-2001)

6 PHOTOS
Hugh Hefner and Brande Roderick together
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Hugh Hefner and Brande Roderick together
388383 01: Playmate Of The Year, Brande Roderick poses with Hugh Hefner at the Playmate Of The Year Party April 26, 2001 in Los Angeles, CA. (Photo by Brad Elterman/Newsmakers)
388435 03: Hugh Hefner hangs out with his Playboy playmates at the Sky Bar for Playboy Playmate of the Year 2001 party for model Brande Roderick April 26, 2001 in Los Angeles, CA. (Photo by Laurence Cottrell/Liaison)
WEST HOLLYWOOD, CA - OCTOBER 19: Model Brande Roderick poses with Playboy founder Hugh Hefner at Barfly on October 19, 2002 in West Hollywood, California. (Photo by David Klein/Getty Images)
LAS VEGAS - MAY 02: Karissa and Kristina Shannon, Brande Roderick, Hugh Hefner and Crystal Harris arrives at Playboy's 50th Annual Playmate of the Year Announcement and Celebration at Palms Hotel & Casino on May 2, 2009 in Las Vegas, Nevada. (Photo by Denise Truscello/WireImage)
Brande Roderick and Hugh Hefner arrives at Playboy's 50th Annual Playmate of the Year Announcement and Celebration at Palms Hotel & Casino on May 2, 2009 in Las Vegas, Nevada. (Photo by Denise Truscello/WireImage)
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Roderick, a “Baywatch” actress, dated Hefner for one year.

Holly Madison (2001-2008)

31 PHOTOS
Hugh Hefner and Holly Madison together
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Hugh Hefner and Holly Madison together
405308 01: Playboy founder Hugh Hefner poses with model Holly Madison outside the BarFly club May 10, 2002 in Hollywood, CA. (Photo by David Klein/Getty Images)
BEVERLY HILLS, CA - SEPTEMBER 25: Hugh Hefner and girlfriend playboy model Holly Madison hug during a birthday party for Hef's two other girlfriends Izabella Kasprzyk and Bridget Marquardt at Joya restaurant on September 25, 2002 in Beverly Hills, California. (Photo by David Klein/Getty Images)
WEST HOLLYWOOD, CA - MARCH 30: Playboy publisher Hugh Hefner (C) gets kisses from Playboy playmates Bridget and Holly Madison (R) at Hefner's 77th birthday party at Barfly March 30, 2003 in West Hollywood, California. (Photo by David Klein/Getty Images)
HOLLYWOOD - APRIL 25: Playboy founder Hugh Hefner poses with playmate Holly Madison at The White Lotus club on April 25, 2003 in Hollywood, California. (Photo by David Klein/Getty Images)
HOLMBY HILLS, CA - MAY 6: (L to R) Playboy bunny Sheila Levell, Playboy founder Hugh Hefner and Playboy bunny Holly Madison perform a scene during the filming of a commercial for 'X Games IX' at the Playboy Mansion May 6, 2003 in Holmby Hills, California. This year's X Games will take place at STAPLES Center in Los Angeles from August 14th through 18th. (Photo by Robert Mora/Getty Images)
Holly Madison, Hugh Hefner, Bridget Marquardt Front Row, Crystal Camden (Photo by Denise Truscello/WireImage)
Holly Madison, Hugh Hefner during The Palms Casino Resort Celebrates Playboy's 50th Anniversary Poolside With Hugh Hefner At Skin at The Palms Casino Resort in Las Vegas, Nevada. (Photo by Denise Truscello/WireImage)
HOLLYWOOD, CA - November 5: Publisher Hugh Hefner and his girlfriend Holly Madison pose in front of Concord November 5, 2003 in Hollywood, California. (Photo by David Klein/Getty Images)
BEVERLY HILLS, CA - JANUARY 16: (L-R) Kendra Wilkinson, Holly Madison, Hugh Hefner and Bridget Marquardt attend HBO Golden Globe Awards After-Party at Griff's Restaurant at the Beverly Hilton Hotel on January 16, 2005 in Beverly Hills, CA. (Photo by Billy Farrell/Patrick McMullan via Getty Images)
BEVERLY HILLS, CA - JULY 17: Playmate Holly Madison and Playboy's Hugh Hefner attend the panel discussion for 'The Girls Next Door' during the E! Networks presentation at the 2005 Television Critics Association Summer Press Tour at the Beverly Hilton Hotel on July 17, 2005 in Beverly Hills, California. (Photo by Frederick M. Brown/Getty Images)
Hugh Hefner and girlfriend Holly Madison during Animal Fair's 6th Annual 'Paws for Style' Pet Fashion Show and Gala Charity Auction - Red Carpet and Show at The Loews Beverly Hills Hotel in Beverly Hills, California, United States. (Photo by J. Merritt/FilmMagic)
Holly Madison, Hugh Hefner and Martine Colette, Wildlife WayStation's Founder and Director at the Playboy Mansion in Beverly Hills, California (Photo by Gregg DeGuire/WireImage)
NEW YORK - OCTOBER 11: Hugh Hefner, editor-in-chief of Playboy magazine, and Holly Madison, of E!'s 'The Girls Next Door,' greet fans as they sign copies of the November issue of Playboy at Virgin Megastore Times Square October 11, 2005 in New York City. (Photo by Paul Hawthorne/Getty Images)
LONDON - MAY 23: (from left to right) Bridget Marquardt, Hugh Hefner, Holly Madison and Kendra Wilkinson attend the playboy entrepreneur's 80th birthday bash in London hosted by E! Entertainment Television at The Play Room on 23 May 2006 in London, England. (Photo by David Westing/Getty Images)
CANNES, FRANCE - MAY 25: Playboy publisher Hugh Hefner poses for a picture next to his playmate girlfriend Holly Madison as she celebrate his 80th birthday during the 59th International Cannes Film Festival May 25, 2006 in Cannes, France. (Photo by Gareth Cattermole/Getty Images)
Rome, ITALY: Playboy magazine founder Hugh Hefner (L) arrives late 01 June 2006 at party with girlfriend Holly Madison, to celebrate his 80th birthday at Villa Miani in Rome. AFP PHOTO / TIZIANA FABI (Photo credit should read TIZIANA FABI/AFP/Getty Images)
LOS ANGELES, CA - JULY 18: Hugh Hefner and Holly Madison attend the Playboy and Skyy Vodka Party on July 18, 2006 in Los Angeles, California. (Photo by Chad Buchanan/Getty Images)
Holly Madison, Hugh Hefner, Bridget Marquardt and Kendra Wilkinson (Photo by Mark Sullivan/WireImage)
Kendra Wilkinson, Hugh Hefner and Holly Madison (Photo by John Sciulli/WireImage)
Kendra Wilkinson, Hugh Hefner, Holly Madison and Bridget Marquardt (Photo by Jamie McCarthy/WireImage)
US Playboy Magazine publisher Hugh Hefner poses with his three girl friends: Holly Madison (L), 26; Bridget Marquardt (2R), 32; and Kendra Wilkinson (R), 21, during a press conference to introduce the new season of Hefner's TV show 'Girls of the Playboy Mansion' on E! Entertainment, 11 January 2007 at the Palyboy Mansion in Beverly Hills. AFP PHOTO/GABRIEL BOUYS (Photo credit should read GABRIEL BOUYS/AFP/Getty Images)
Hugh Hefner and Holly Madison during Hugh Hefner's 81st Birthday Weekend - Birthday Dinner at Nine Steakhouse at The Palms Hotel and Casino Resort at Nine Steakhouse at The Palms Hotel and Casino Resort in Las Vegas, Nevada. (Photo by Denise Truscello/WireImage)
Holly Madison and Hugh Hefner (Photo by Denise Truscello/WireImage)
LOS ANGELES, CA - MAY 03: Hugh Hefner and Holly Madison attend the 2007 Playmate of the Year party at the Playboy Mansion on May 3, 2007 in Los Angeles, California. (Photo by Chad Buchanan/Getty Images)
Holly Madison and Hugh Hefner (Photo by Enos Solomon/FilmMagic)
Monaco, MONACO: Playboy Magazine publisher Hugh Hefner (C) poses with playmates Holly Madison (L) and Bridget Marquardt (R), 12 june 2007 during a photocall at the 47th Monte Carlo Television Festival in Monaco. AFP PHOTO VALERY HACHE (Photo credit should read VALERY HACHE/AFP/Getty Images)
Holly Madison, Hugh Hefner, Bridget Marquart and Kendra Wilkinson (Photo by Tony Barson/WireImage)
BEVERLY HILLS, CA - FEBRUARY 21: Hugh Hefner and Holly Madison attend Byblos Event at the Playboy Mansion at Playboy Mansion on February 21, 2008 in Beverly Hills, CA. (Photo by BRIAN LINDENSMITH/Patrick McMullan via Getty Images)
LOS ANGELES, CA - AUGUST 07: Playmate Holly Madison and Hugh Hefner are denied access to the Grand Opening of Affliction on Melrose Avenue because it was over capacity and shut down by the Fire Marshal on August 7, 2008 in Los Angeles, California. (Photo by Tiffany Rose/WireImage)
LAS VEGAS - JULY 18: Television personality and model Holly Madison (L) and Playboy founder Hugh Hefner appear in Madison's dressing room after Hefner attended the adult production, 'PEEPSHOW' starring Madison at the Planet Hollywood Resort & Casino July 18, 2009 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images for BASE Entertainment)
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Holly Madison was Hefner’s girlfriend for seven years. She moved in to the mansion when she was 21-years-old and left at the age of 28.

Tina Marie Jordan (2000-2001)

5 PHOTOS
Hugh Hefner and Tina Maria Jordan together
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Hugh Hefner and Tina Maria Jordan together
393760 01: (L to R) Playmate Tina Jordan, Playboy editor Hugh Hefner, singer Gina Boccadis, actor Kevin Spacey and Playboy''s Miss September 2001 Dalene Kurtis pose during a private Playboy party August 25, 2001 in Beverly Hills, CA. (Photo by David Klein/GettyImages)
394235 03: Playboy founder Hugh Hefner poses with model Tina Jordan (L) and female wrestler Chyna at the Premiere Playboy Cover Release Party for Miss October 2001 Stephanie Heinrich September 7, 2001 at Barfly in West Hollywood, CA. (Photo by David Klein/Getty Images)
401246 19: Playboy founder Hugh Hefner poses with Miss March 2002 playmate Tina Jordan at Barfly club during Jordans premiere Playboy Playmate Release Party February 15, 2002 in West Hollywood, CA. (Photo by David Klein/Getty Images)
404541 10: Model Tina Jordan poses with Playboy founder Hugh Hefner during Playboy's 2002 Playmate Of The Year party for Dalene Kurtis April 25, 2002 in Los Angeles, CA. (Photo by David Klein/Getty Images)
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Tina was Hefner’s girlfriend for one year.

Izabella St. James (2002-2004)

Izabella met Hefner when she was 26-years-old and in law school.

She was invited to move into the mansion and become Hefner’s girlfriend in 2002.

She ended up writing a tell all book titled “Bunny Tales: Behind Closed Doors at the Playboy Mansion.”

Bridget Marquardt (2002-2009)

11 PHOTOS
Hugh Hefner and Bridget Marquardt together
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Hugh Hefner and Bridget Marquardt together
BEVERLY HILLS, CA - SEPTEMBER 25: Playboy models Izabella Kasprzyk (L) and Bridget Marquardt (R) pose with boyfriend Hugh Hefner (C) during their birthday dinner party at Joya restaurant on September 25, 2002 in Beverly Hills, California. (Photo by David Klein/Getty Images)
BEVERLY HILLS, CA - JULY 12: Playboy's Hugh Hefner and his Playmates, Kendra Wilkinson (L), Bridget Marquardt and Holly Madison (R) arrive at 'Fight for Victory', the 13th Annual Espy Pre-Party hosted by Andy Roddick at the Playboy Mansion on July 12, 2005 in Beverly Hills, California. (Photo by Kevin Winter/Getty Images)
LAS VEGAS - NOVEMBER 04: Playboy founder and Editor-in-Chief Hugh Hefner and his girlfriend, Playboy Playmate Bridget Marquardt, attend a fashion show to introduce new Playboy Bunny costumes designed by Roberto Cavalli during a party for the fourth anniversary of the Palms Casino Resort November 4, 2005 in Las Vegas, Nevada. The costumes will be featured in the new Playboy Club Las Vegas in the Palms' Fantasy Tower, scheduled to open in May 2006. (Photo by Ethan Miller/Getty Images)
Bridget Marquardt and Hugh Hefner during 2006 Cannes Film Festival - Seen Around Cannes - Day 10 at Cannes in Cannes, France. (Photo by Niki Nikolova/FilmMagic)
ROME, ITALY - JUNE 1: Playboy founder Hugh Hefner (C) and his girlfriends Bridget Marquardt (L) and Holly Madison (R) attend a party to celebrate his 80th birthday, and 50 years of Playboy, at Villa Miani on June 1, 2006 in Rome, Italy. (Photo Elisabetta Villa/Getty Images)
Holly Madison, Hugh Hefner, Bridget Marquardt and Kendra Wilkinson (Photo by Jamie McCarthy/WireImage)
Bridget Marquardt and Hugh Hefner during Hugh Hefner's 81st Birthday Weekend - Birthday Dinner at Nine Steakhouse at The Palms Hotel and Casino Resort at Nine Steakhouse at The Palms Hotel and Casino Resort in Las Vegas, Nevada. (Photo by Denise Truscello/WireImage)
Holly Madison, Hugh Hefner and Bridget Marquardt (Photo by Tony Barson/WireImage)
BEVERLY HILLS, CA - FEBRUARY 21: Bridget Marquardt and Hugh Hefner attend Byblos Event at the Playboy Mansion at Playboy Mansion on February 21, 2008 in Beverly Hills, CA. (Photo by BRIAN LINDENSMITH/Patrick McMullan via Getty Images)
LOS ANGELES, CA - MARCH 10: Playboy Magazine founder Hugh Hefner and Playmate Bridget Marquardt arrive at the premiere of The Travel Channel's 'Bridget's Sexiest Beaches' held at the Playboy Mansion on March 10, 2009 in Los Angeles, California. (Photo by Alberto E. Rodriguez/Getty Images)
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Bridget was one of the original cast on “Girls Next Door” and dated Hefner along with Holly Madison and Kendra Wilkinson.

Kristina and Karissa Shannon 2008-2010)

9 PHOTOS
Hugh Hefner with Kristina and Karissa Shannon
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Hugh Hefner with Kristina and Karissa Shannon
BEVERLY HILLS, CA - MARCH 10: TV personalities Karissa Shannon, Kristina Shannon, Hugh Hefner and Crystal Harris attend The Travel Channel's 'Bridget's Sexiest Beaches' launch party at The Playboy Mansion on March 10, 2009 in Beverly Hills, California. (Photo by Jason LaVeris/FilmMagic)
LAS VEGAS - APRIL 04: Kristina Shannon, Karissa Shannon, Hugh Hefner and Crystal Harris attends Hugh Hefner's 83rd birthday pool party at Palms Place at the Palms Resort & Casino on April 4, 2009 in Las Vegas, Nevada. (Photo by Denise Truscello/WireImage)
BEVERLY HILLS, CA - MAY 16: (L-R) Crystal Harris, Hugh Hefner, Karissa Shannon and Kristina Shannon attend the Stars And Stripes Evening Of Sexy Patriotism at The Playboy Mansion on May 16, 2009 in Beverly Hills, California. (Photo by Michael Bezjian/WireImage)
HOLLYWOOD - JUNE 13: Playboy founder Hugh Hefner and girlfriends (L-R) Kristina Shannon, Karissa Shannon and Crystal Harris attend the 31st annual Playboy Jazz Festival at the Hollywood Bowl on June 13, 2009 in Hollywood, California. (Photo by David Livingston/Getty Images)
HOLLYWOOD - AUGUST 27: (L-R) Kristina Shannon, Karissa Shannon, Hugh Hefner and guest arrive to the 9th Annual Celebrity Catwalk Fashion Show held at The Highlands Club in the Hollywood & Highland Center on August 27, 2009 in Hollywood, California. (Photo by Michael Tran/FilmMagic)
LOS ANGELES, CA - OCTOBER 13: Hugh Hefner, and The 'new' Girls Next Door Karissa Shannon, Kristina Shannon and Crystal Harris arrive at the 2009 Fox Reality Channel Really Awards at The Music Box at the Fonda Hollywood on October 13, 2009 in Los Angeles, California. (Photo by Jeffrey Mayer/WireImage)
LOS ANGELES, CA - DECEMBER 10: (L-R) Models Karissa Shannon, playboy founder Hugh Hefner, model Crystal Harris and model Kristina Shannon attend the Hugh Hefner Autographs Limited Edition Six-Volume Anthology Party by Taschen on December 10, 2009 in Los Angeles, California. (Photo by Michael Bezjian/WireImage)
LOS ANGELES, CA - FEBRUARY 10: (L-R) Kristina Shannon, Hugh Hefner, and Karissa Shannon arrive at the 2012 MusiCares Person of the Year Tribute To Paul McCartney held at the Los Angeles Convention Center on February 10, 2012 in Los Angeles, California. (Photo by Jason Merritt/Getty Images)
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The twins moved into the mansion in 2008 and were also part of “Girls Next Door.”

Hefner apparently kicked them out of the mansion for having younger boyfriends come over.

Crystal Harris 

16 PHOTOS
Hugh Hefner and Crystal Harris together
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Hugh Hefner and Crystal Harris together
LAS VEGAS - APRIL 04: Crystal Harris and Hugh Hefner attend Hugh Hefner's 83rd birthday dinner at Nine Steakhouse at the Palms Resort & Casino on April 4, 2009 in Las Vegas, Nevada. (Photo by Denise Truscello/WireImage)
LAS VEGAS - MAY 02: 2009 Playmate of the Year Ida Ljungqvist, Hugh Hefner and Crystal Harris attend the Playboy Club at The palms Casino Resort on May 2, 2009 in Las Vegas, Nevada. (Photo by Denise Truscello/WireImage)
HOLLYWOOD - JUNE 13: Playboy founder Hugh Hefner (L) and girlfriend Crystal Harris attend the 31st annual Playboy Jazz Festival at the Hollywood Bowl on June 13, 2009 in Hollywood, California. (Photo by David Livingston/Getty Images)
LOS ANGELES, CA - AUGUST 27: Hugh Hefner and Crystal Harris arrive on the red carpet at the Celebrity Catwalk's 9th Annual Fashion Show on August 27, 2009 in Los Angeles, California. (Photo by Heather Holt/Getty Images)
LOS ANGELES, CA - NOVEMBER 19: Hugh Hefner and Crystal Harris attend the Los Angeles TASCHEN book launch party at Cross Roads Of The World on November 19, 2009 in Los Angeles, California. (Photo by Michael Caulfield/WireImage)
LOS ANGELES, CA - DECEMBER 10: Playboy founder Hugh Hefner and model Crystal Harris attend the Hugh Hefner Autographs Limited Edition Six-Volume Anthology Party by Taschen on December 10, 2009 in Los Angeles, California. (Photo by Michael Bezjian/WireImage)
HOLLYWOOD - APRIL 26: Hugh Hefner (L) and Crystal Harris arrive at the 'Iron Man 2' World Premiere at El Capitan Theatre on April 26, 2010 in Hollywood, California. (Photo by Jeff Vespa/WireImage)
Playboy owner Hugh Hefner arrives with Playmate and actress Crystal Harris at the world premiere of the restored 'A Star is born' during the opening Night Gala of the 2010 TCM Classic Film Festival in Hollywood, California, on April 23, 2010. AFP PHOTO / GABRIEL BOUYS (Photo credit should read GABRIEL BOUYS/AFP/Getty Images)
LAS VEGAS - OCTOBER 21: Hugh Hefner (L) and Crystal Harris attend Crazy Horse Paris at the MGM Resort & Casino on October 21, 2010 in Las Vegas, Nevada. (Photo by Denise Truscello/WireImage)
Hugh Hefner and Crystal Harris attend 20th annual Literary Awards Festival at Beverly Hills Hotel on November 17, 2010 in Beverly Hills, California. (Photo by Brian To/FilmMagic)
HOLLYWOOD, CA - APRIL 28: Playboy founder Hugh Hefner (L) and his fiancee Crystal Harris attend the TCM Classic Film Festival Opening Night Gala and World Premiere of the film 'An American In Paris' at Grauman's Chinese Theatre on April 28, 2011 in Hollywood, California. (Photo by Frederick M. Brown/Getty Images)
BEVERLY HILLS, CA - APRIL 30: Hugh Hefner and Crystal Harris attend the 55th Anniversary Thalians Gala Honoring Hugh Hefner at The Playboy Mansion on April 30, 2011 in Beverly Hills, California. (Photo by Craig Barritt/WireImage)
Hugh Hefner and Crystal Harris attend the opening of 'Playboy Club London' at playboy Club on June 4, 2011 in London, England.
BEVERLY HILLS, CA - AUGUST 07: Playboy founder Hugh Hefner (L) and TV personality Crystal Harris attend the Beverly Hills City Council and Playboy Enterprises, Inc.'s celebration of the return of Playboy headquarters to Beverly Hills on August 7, 2012 in Beverly Hills, California. (Photo by David Livingston/Getty Images)
HOLMBY HILLS, CA - MAY 09: Crystal Harris (L) and Hugh Hefner attend Playboy's 2013 Playmate Of The Year luncheon honoring Raquel Pomplun at The Playboy Mansion on May 9, 2013 in Holmby Hills, California. (Photo by Charley Gallay/Getty Images for Playboy)
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Crystal Harris and Hugh Hefner got married on New Year’s Eve in 2012. He was 86-years-old and she was 26-years-old at the time.

Read original story Hugh Hefner’s Wives and Girlfriends Through the Years (Photos) At TheWrap

66 PHOTOS
Hugh Hefner through the years
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Hugh Hefner through the years
LOS ANGELES - JUNE 26,1957: Hugh Hefner with Joan Bradshaw at a Play Boy Party in Los Angeles, California. (Photo by Earl Leaf/Michael Ochs Archives/Getty Images)
LOS ANGELES - JUNE 26: Playboy Magazine founder and publisher Hugh Hefner attends a party in his honor with actresses Joan Bradshaw (right) and Susanne Sidney on June 26, 1957 in Los Angeles, California. (Photo by Earl Leaf/Michael Ochs Archives/Getty Images)
LOS ANGELES - JUNE 26,1957: Hugh Hefner and guest at a Play Boy Party in Los Angeles, California. (Photo by Earl Leaf/Michael Ochs Archives/Getty Images)
LOS ANGELES - JUNE 26,1957: Hugh Hefner with Joan Bradshaw and girls at a Play Boy Party in Los Angeles, California. (Photo by Earl Leaf/Michael Ochs Archives/Getty Images)
American pornographer Hugh Hefner and murdered Playboy PLaymate Dorothy Stratten (1960 - 1980), 1980. She holds a plaque naming her 1980 Playmate of the Year. (Photo By Julian Wasser/Online USA Inc./Getty Images)
American publisher Hugh Hefner smokes a pipe and holds a pamphlet while balancing a briefcase on his knee, c. 1960. (Photo by Authenticated News/Getty Images)
Show Business Illustrated magazine
(Original Caption) 1/29/1962 -New York,NY -: Hugh M. Hefner, Editor and Publisher of Playboy, is shown with Cynthia Maddox, the blond cover girl on the February issue of his magazine, arriving by TWA superjet from Chicago. They are here to attend a party given by Ella Fitzgerald at the Basin Street East in honor of winners of the Playboys jazz poll.
(Original Caption) Hugh Hefner, publisher of Playboy Magazine, shown as he appeared in court to face charges that nude photograph of Jayne Mansfield in the June issue are obscene. Hefner's attorneys asked for a continuance and his trial was set for July 9 in Municipal Court.
26th June 1966: American millionaire Hugh Hefner, founder of the Playboy empire, during a visit to Britain. (Photo by John Downing/Express/Getty Images)
Playboy editor and tycoon Hugh Hefner is greeted by a group of bunny girls from his Playboy Clubs, upon his arrival at London Airport. (Photo by Dove/Getty Images)
Heff, is in Britain to officially open his 16th Playboy Club, located in Park Lane, London. (Photo by Sunday People/Mirrorpix/Mirrorpix via Getty Images)
Hugh Hefner Boss of the Playboy Empire arrives with an entourage of Bunny Girls at London Heathrow Airport, Saturday 25th June 1966. Heff, is in Britain to officially open his 16th Playboy Club, located in Park Lane, London. (Photo by Sunday People/Mirrorpix/Mirrorpix via Getty Images)
Playboy CEO Hugh Hefner with partner model, actress and singer Barbara Benton arrive at Paris Airport. (Photo by James Andanson/Sygma via Getty Images)
(GERMANY OUT) Hefner, Hugh *09.04.1926-Verleger (Playboy), USA - mit seiner Freundin Barbara Benton waehrend eines Besuchs in Berlin- 1969 (Photo by Binder/ullstein bild via Getty Images)
Portrait taken on August 21, 1970 at Le Bourget airport shows US Playboy Magazine publisher Hugh Hefner and his girlfriend actress Barbara Benton. AFP PHOTO (Photo credit should read STRINGER/AFP/Getty Images)
UNSPECIFIED - CIRCA 1970: Photo of Hugh Hefner (Photo by Michael Ochs Archives/Getty Images)
UNSPECIFIED - CIRCA 1970: Photo of Hugh Hefner Photo by Michael Ochs Archives/Getty Images
Publisher Hugh Hefner and Actress Julie Newmar attend the Rugby Ball on October 20, 1972 in New York City, New York. (Photo by Ron Galella/WireImage)
HUGH HEFNER -- Pictured: (l-r) Hefner's girlfriend/Singer, Barbi Benton, unknown, Playboy founder Hugh Hefner discussing promotional artwork for Barbi's 1974 debut album 'Barbi Doll'-- Photo by: Ron Tom/NBCU Photo Bank
American publisher Hugh Hefner, of Playboy Enterprises, smiles with his girlfriend, American actor and model Barbi Benton as they attend the 21st annual SHARE fund raiser for The Exceptional Children's Foundation. She wears a feathered blouse and he holds a pipe. (Photo by Frank Edwards/Getty Images)
Hugh Hefner and bunnies during 5th Annual International B Bunny of the Year Pageant at The Beverly Hilton Hotel in Beverly Hills, California, United States. (Photo by Ron Galella/WireImage)
Hugh Hefner and Sondra Theodore attend Hugh Hefner's Special 25th Anniversary Party on January 10, 1978 at New York New York Disco in New York City. (Photo by Ron Galella/WireImage)
Hugh Hefner and Sondra Theodore attend 25th Anniversary Party for Playboy Magazine on January 11, 1979 at Tavern on the Green in New York City. (Photo by Ron Galella/WireImage)
NEW YORK, NY - CIRCA 1979: Hugh Hefner and Sondra Theodore circa 1979 in New York City. (Photo by Images Press/IMAGES/Getty Images)
375250 01: Mid-1980's Playboy Mansion. Hugh Hefner and girlfriend Carrie Leigh at the Playboy Mansion.
Sondra Theodore and Hugh Hefner (Photo by Ron Galella/WireImage)
circa 1980: 'Playboy' magazine founder and publisher Hugh Hefner with 1980 Playboy Playmate of the Year, Canadian model and actor Dorothy Stratten. Stratten wears a strapless top and flowers in her hair. (Photo by Frank Edwards/Fotos International/Getty Images)
THE TOMORROW SHOW -- Pictured: (l-r) Playboy founder/publisher Hugh Hefner, journalist/Playboy covergirl Rita Jenrette at the Playboy Mansion -- Photo by: Paul Drinkwater/NBCU Photo Bank
Hugh Hefner and Carrie Lee attend the opening party for 'Private Lives' on October 13, 1983 at Madame Wu's Restaurant in Beverly Hills, California. (Photo by Ron Galella/WireImage)
Hugh Hefner and playboy bunnies are photographed October 29, 1985 at the re-opening of the Playboy Club in New York City. (Photo by Yvonne Hemsey/Getty Images)
Hugh Hefner and Carrie Lee attends the premiere of 'Beverly Hills Cop II' on May 19, 1987 at Mann Chinese Theater in Hollywood, California. (Photo by Ron Galella, Ltd./WireImage)
LOS ANGLES, CA - 1989: Playboy Magazine founder and publisher, Hugh Hefner, announces his engagement to Playmate of the Year Kimberly Conrad at a 1989 Los Angeles, California, press conference. Hefner and Conrad divorced in 2003. (Photo by George Rose/Getty Images)
368600 12: Hugh Hefner and friends, Jessica Paisley, left, Mandy Bentley and Sandy Bentley arrive for the 10th Anniversary celebration of the hit television show, 'Baywatch' on May 2, 2000 in Santa Monica, CA. The show has aired nearly 200 episodes since it first premiered in 1990. (Photo by Joe Thomas/Online USA)
Kimberly Conrad, Marsden Hefner, and Hugh Hefner during Christie Hefner Hosts Open House Gala for New Headquarters at Playboy Headquarters in Beverly Hills, California, United States. (Photo by Jim Smeal/WireImage)
Hugh Hefner and Kimberley Conrad in Photo Booth (Photo by Frank Trapper/Corbis via Getty Images)
Nancy Sinatra and Hugh Hefner attend Playboy Magazine Party on April 6, 1995 at the Playboy Mansion in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
The Rembrandts, Yasmin Bleeth, Hugh Hefner & Playboy Bunnies (Photo by SGranitz/WireImage)
Hugh Hefner, wife Kimberly and their children during Premiere of 'Star Wars: Special Edition' In 1997 at Westwood in Westwood, CA, United States. (Photo by Magma Agency/WireImage)
Playmate Heather Kozar and businessman Hugh Hefner attend Playboy Announces Heather Kozar as the 1999 Playmate of the Year on April 29, 1999 at The Playboy Mansion in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
7/17/99 Los Angeles, Ca. Hugh Hefner Dancing With Playboy Gals At The Playboy Expo '99 & Playmate Reunion Held At The Pacific Design Center. (Photo By Brad Elterman/Getty Images)
7/16/99 Beverly Hills, CA Hugh Hefner, Shannon Tweed, and Diane Hunter (1954 Playmate) at the First-Ever Playboy Expo. The expo gave a chance for fans to meet centerfolds, celebrities, Bunnies, wirters, artists, photographers, and cartoonists. Photo Brad Elterman/Online USA, Inc.
CANNES, FRANCE: Playboy magazine president Hugh Hefner (C) poses with playmates 14 May 1999 on the steps of the Palais des Festivals before the screening of their movie 'Entrapment' in selection for the 52nd Cannes Film Festival. (ELECTRONIC IMAGE) (Photo credit should read PASCAL GUYOT/AFP/Getty Images)
BEVERLY HILLS, CA - APRIL 29: Hugh Hefner attends Playmate of the Year Press Conference on April 29, 1999 at the Playboy Mansion in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
Brandi and Hugh Hefner during Madonna's new CD Music Party in Los Angeles, California, United States. (Photo by Jeff Kravitz/FilmMagic, Inc)
Madonna, Hugh Hefner & Playboy Bunnies (Photo by Kevin Mazur/WireImage)
WEST HOLLYWOOD, CA - DECEMBER 18: Playboy founder Hugh Hefner poses with unidentified model, Shauna Sand (2nd from L) and Holly Madison (R) during Barfly 5th year anniversary party on December 18, 2002 in West Hollywood, California. (Photo by David Klein/Getty Images)
Hugh Hefner and Playboy Playmates during Ben Stiller and Christine Taylor Host a Grand Classics Screening of 'Sweet Smell of Success' with YSL at the Playboy Mansion at Playboy Mansion in Beverly Hills, California, United States. (Photo by Donato Sardella/WireImage for Harrison & Shriftman)
Hiromi Oshima, Playboy Miss June 2004, Holly Madison, Hugh Hefner, Bridget Marquardt , Kendra Wilkinson, Sara Jean Underwood, Playboy Playmate of the Year 2007 and guest (Photo by Enos Solomon/FilmMagic)
Hugh Hefner and models during Hugh Hefner Inducted Into The Erotic Museum's Hall Of Fame at The Erotic Museum in Hollywood, United States. (Photo by Laurence Cottrell/FilmMagic)
(EXCLUSIVE, Premium Rates Apply) Carmen Electra and Hugh Hefner *EXCLUSIVE COVERAGE* (Photo by Michael Bezjian/WireImage for Playboy Enterprises)
Carmen Electra, top row far left, Hugh Hefner, center, The Girls Next Door and Playmates *EXCLUSIVE COVERAGE* ***Exclusive*** (Photo by Michael Bezjian/WireImage for Playboy Enterprises)
Hugh Hefner and girlfriends during The 21st Annual American Cinematheque Award Honoring George Clooney - Arrivals at Beverly Hilton Hotel in Beverly Hills, California, United States. (Photo by Jason Merritt/FilmMagic)
LOS ANGELES, CA - DECEMBER 16: Playboy founder Hugh Hefner attends a book signing of 'Mr. Playboy: Hugh Hefner and the American Dream' at Barnes N Noble bookstore on Tuesday December 16, 2008 in Los Angeles, California. (Photo by Byron Gamarro/Getty Images)
LAS VEGAS - MAY 15: (L-R) Model Hope Dworaczyk, Playboy founder Hugh Hefner and his girlfriend, December 2009 Playboy Playmate of the Month Crystal Harris, arrive at a party introducing Dworaczyk as the 2010 Playboy Playmate of the Year at the Rain Nightclub inside the Palms Casino Resort May 15, 2010 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)
BEVERLY HILLS, CA - DECEMBER 10: Hugh Hefner and Pamela Anderson attend the Hugh Hefner book signing session at Taschen on December 10, 2009 in Beverly Hills, California. (Photo by Riccardo S. Savi/Getty Images)
LOS ANGELES, CA - DECEMBER 09: Playboy founder Hugh Hefner (L) and model Crystal Harris attend an event celebrating the expansion of Griffith Park at Lake Hollywood Park on December 9, 2010 in Los Angeles, California. (Photo by David Livingston/Getty Images)
LOS ANGELES, CA - OCTOBER 13: Hugh Hefner attends 'The Rum Diary' Los Angeles Premiere at LACMA on October 13, 2011 in Los Angeles, California. (Photo by Steve Granitz/WireImage)
BEVERLY HILLS, CA - SEPTEMBER 19: Playboy Founder Hugh Hefner (C) arrives at the 2011 Ella Awards at The Beverly Hilton hotel on September 19, 2011 in Beverly Hills, California. (Photo by Paul Archuleta/FilmMagic)
BEVERLY HILLS, CA - AUGUST 07: (L-R) Hugh Hefner and Crystal Harris attend the Beverly Hills City Council and Playboy Enterprises ribbon-cutting ceremony for Beverly Hills Playboy World Headquarters on August 7, 2012 in Beverly Hills, California. (Photo by Tibrina Hobson/WireImage)
HOLLYWOOD, CA - JUNE 15: Publisher Hugh Hefner attends a press conference at the 35th Anniversary Playboy Jazz Festival - Day 1 at the Hollywood Bowl on June 15, 2013 in Hollywood, California. (Photo by Rodrigo Vaz/Getty Images)
Los Angeles, CA - OCTOBER 25: Hugh Hefner and Crystal Hefner attend Playboy Mansion's Annual Halloween Bash at The Playboy Mansion on October 25, 2014 in Los Angeles, California. (Photo by Charley Gallay/Getty Images for Playboy)
LOS ANGELES, CA - JANUARY 16: Hugh Hefner (C) poses with Playboy Bunnies Playmate of the Year 2013 Raquel Pomplun (2nd L) and Miss December 2009 Crystal Hefner (2nd R) at Playboy's 60th Anniversary special event on January 16, 2014 in Los Angeles, California. (Photo by Rachel Murray/Getty Images for Playboy)
LOS ANGELES, CA - JANUARY 16: Cooper Hefner (L) and Hugh Hefner pose at Playboy's 60th Anniversary special event on January 16, 2014 in Los Angeles, California. (Photo by Charley Gallay/Getty Images for Playboy)
LAS VEGAS, NV - FEBRUARY 20: Impersonator George Kane of Florida as Hugh Hefner presents an award during The Reel Awards 2017 at the Golden Nugget Hotel & Casino on February 20, 2017 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)
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