Hugh Hefner

Kristina and Karissa Shannon with Hugh Hefner at the 31st annual Playboy Jazz Festival in Hollywood in 2009.

Playboy Twin Reemerges for Rare Solo Interview

The cover girl and her sister left the Playboy Mansion 15 years ago.

Roosa Rahkonen

Models Holly Madison and Tiffany Holiday hug Playboy founder Hugh Hefner (center) during a birthday dinner party for Hef's two other girlfriends, Bridget Marquardt and Izabella Kasprzyk, in Beverly Hills, California, on September 12, 2002 in Beverly Hills, California.

Hugh Hefner’s Ex Reveals Post-Pregnancy Surgery Scars

The former Playboy model is sharing her plastic surgery secrets.

Tamilore Oshikanlu

Kendra Wilkinson and Hugh Hefner at Hefner's 83rd birthday dinner at Nine Steakhouse in Las Vegas in 2009.

'WHO'S PAYING?'

Hugh Hefner’s Ex Slams Comments Saying She ‘Aged Awfully'

“Bring it down a few sizes.”

Roosa Rahkonen

Hef and Holly.

Hugh Hefner’s Ex Reveals ‘Really Weird’ Sex Ritual

“It was disgusting,” recalls Holly Madison.

Mary Papenfuss

Hugh Hefner with many of his exgirlfriends.

It’s Hugh Hefner’s 100th Birthday—Where Are His Exes Now?

The legendary Playboy founder dated countless women and married three. This is what they’re up to as of 2026.

Roosa Rahkonen

Hugh Hefner and Crystal Hefner attend Playboy Mansion's Annual Halloween Bash at The Playboy Mansion on October 25, 2014.

Hugh Hefner’s Widow Marries New Beau Three Years Her Senior

Harris was married to Hugh Hefner from 2012 until his death at age 91 in 2017.

Muskaan Arshad