Crystal Hefner Says Leonardo DiCaprio Is the 'New Hef' as She Recalls His Former Hookup With Rihanna

The next generation’s Hugh Hefner?

On Wednesday, March 6, the late Playboy publisher’s wife, Crystal Hefner, commented on the similarities she sees between Leonardo DiCaprio and Hugh. The 37-year-old widow also revealed she once saw Leo and Rihanna cozying up in the Playboy mansion years ago.

“Leo DiCaprio is turning into the new Hef,” she stated of the Titanic star, 49, who is currently dating 25-year-old Italian model Vittoria Ceretti.

“The girls [girlfriends] are getting younger and I'm like, 'Oh God, it's a bad look,'” Crystal added on the “Carrie and Tommy” podcast.

She then alleged The Departed alum and the “Umbrella” singer “hooked up” at the Playboy mansion, when Rihanna, 36, was just in her 20s.

“I remember Leonardo DiCaprio and Rihanna hooking up one night,” she said. “I remember thinking, 'That’s smart, hook up with each other and then we won't tell anyone.'”

Crystal then named other Hollywood stars she saw at the famous house.

“I remember Jack Nicholson would come there a lot. Random celebrities like Pauly Shore, Corey Feldman [too],” she stated. “Others came once in a while just to check it out — Justin Bieber, Kylie Jenner. They just came by to check it out, and I understand their curiosity.”

As OK! previously reported, Leo’s connection to Rihanna was not the only intimate moment of his that has been aired out in the media as of late.

In the March 2024 Dutch edition of Playboy magazine, model Hieke Konings, 22, recounted being unimpressed after smooching the Killers of the Flower Moon actor.

“It was in a secret club in L.A., one of those clubs where you can only get in by invitation,” she shared. “I saw him sitting there in his black hoodie and black cap, and we made eye contact.”

Leo’s manager then approached her “less than a minute later” to tell her the A-lister wanted to talk to her. “Then I walked to his table and sat next to him,” Hieke explained.

“We kissed for a while, and then he asked me to come home with him,” she claimed. “I said no. He reacted very shocked. Of course he wasn’t used to it. When I said I didn’t know him well enough, he responded sweetly, ‘I respect that.’ Whereupon he turned to another girl and took her home!”

Heike described the makeout as “OK” but “definitely not the best” before she revealed why she turned Leo down.

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“I had heard from other girls that he could be very strange,” she alleged. “For example, one friend said he kept his earphones in during s-- because he didn’t want to hear her — and another said he even put a pillow on her head. Leo is too weird and too old.”