By Katie Gray

It’s the end of an era. American icon, publishing pioneer, activist and the ultimate Playboy – sadly passed away recently, at age 91. RIP Hugh Hefner! Since being founded in 1953, Playboy has been a notable American men’s magazine that specializes in lifestyle and entertainment. Of course it is most notable for featuring beautiful women. What would a Playboy be without beautiful women? The gorgeous women featured on the cover and in the magazine, are known as Playmates and Centerfolds. Playboy enterprises is a huge company, with many different divisions. They have accessories and clothing to Playboy TV. From 2005 until 2010, Hugh Hefner and his girlfriends, starred in the E! reality series The Girls Next Door. It starred Hugh Hefner, and the celebrity couple – his three girlfriends: Holly Madison, Bridget Marquardt and Kendra Wilkinson. Who could forget the theme song “Come on-a My House” and the funny adventures that played out on the screen? Hugh Hefner has notoriety for always being surrounded by beautiful women, and dating several of them at once. Hefner was married a couple of times, and is the father of four children. His celebrity relationships were always highly publicized. They often all lived with him at the famous Playboy Mansion. It doesn’t feel real that Hef is gone, but his memory and Playboy – will live on!

Cupid has compiled the 5 Best Playboy Playmate Celebrity Relationships:

1. Holly, Bridget & Kendra: Come on-a My House! Perhaps Hugh Hefner’s most famous celebrity relationship, was with Holly Madison, Bridget Marquardt, and Kendra Wilkinson. The three lovely ladies, alongside Hefner, starred on the hit reality series “The Girls Next Door” on E! The show revolved around the lives of Hef and the girls. The three girls, also shot the front and back cover, of Playboy magazine. They also had photoshoots that were featured inside the pages of Playboy. The show was a success, and the audience loved being able to see the personality behind the four stars. All of them have gone on to have successful careers, endeavors and families. These American beauties, really were the classic girls next door.

2. Barbi Benton: Barbi Doll. From 1969-1976, Barbi Benton was in a celebrity relationship with Hugh Hefner. She is credited with finding and discovering the famous Playboy Mansion, that became a landmark. Barbi Benton was a model and actress. She appeared on the cover of Playboy four times! When Hefner first asked her out on a date, she replied, “I don’t know, I’ve never dated someone over 24 before.” To which he replied, “That’s alright, neither have I.” The two dated for years, lived together, and always remained friends. She is happily married, and is a mother.

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3. Kimberley Conrad: Actress and model, Kimberley Conrad, was married to Hugh Hefner. The pretty pair, had two children together – two boys. Conrad was ‘Playmate of the Month’ in 1988 and in 1989 she won the prized title of ‘Playmate of the Year.’ They married in 1989 and divorced in 2010, when their youngest son turned 18. After 9 years of marriage, they separated and she lived in the house right next door. They all remained a family unit!

4. Brande Roderick: Baywatch Babe! Model and actress, Brande Roderick, is known for her appearances in Playboy and Baywatch. From 1999-2000 she was in a celebrity relationship with Hugh Hefner. In 2000 she was ‘Playmate of the Month’ and then became the ultimate ‘Playmate of the Year’ in 2001. This American beauty has a lot of film and television credits to her name: Starsky & Hutch, The Nanny Diaries, Joey, The Parkers, Beverly Hills 90210, and many more. She is now married, a mother, and is still working in the industry.

Related Link: 6 Best Rock & Roll Celebrity Couples

5. Crystal Hefner: Crystal Hefner, a model and DJ, was Hugh Hefner’s wife – and his last celebrity relationship. The pair married on December 31st, 2012, and tied the knot at the Playboy Mansion. Crystal Hefner was previously the Playboy ‘Playmate of the Month’ for December 2009. The pair remained married until his death, she is now the widow of Hugh Hefner.

Who are your favorite Playboy Playmates that Hugh Hefner was in a celebrity relationship with? Comment below!