Playboy

ONE is an Oscar-winning heart-throb, while the other was an adult magazine magnate – so what could Leonardo DiCaprio and the late Playboy boss Hugh Hefner possibly have in common?Far more than you might imagine.Leonardo with some typically young female friends on a break in the Caribbean isle of St Barts in January last yearCredit: The Mega AgencyHefner at 2006 Hollywood bash with, from left, US TV personalities Kendra Wilkinson, Bridget Marquardt and Holly MadisonCredit: WENNIn 2012, during a party on a yacht in Sydney, some models started removing their bikini tops as the star and his actor pal Jonah Hill enjoyed their companyCredit: Insight News & FeaturesOr as Hugh’s widow Crystal herself says: “Leo DiCaprio is turning into the new Hef.”And she adds that the magazine’s founder, who died aged 91 in 2017, shared a passion with Leo for far younger women.Crystal, 37, who was 60 years younger than her three-times-married husband, says it is “a bad look’’ that the Titanic actor is currently dating 25-year-old Italian model Vittoria Ceretti, who is just over half his age.Crystal also claims that Leonardo, 49, once “hooked up” with singer Rihanna at a Playboy mansion party.READ MORE IN SHOWBIZThat might come as a surprise, but the Oscar-winning actor was often said to be at glamorous events arranged by Hugh.Never-married star Leo, whose previous girlfriends include supermodels Gisele Bundchen, Helena Christensen and Bar Refaeli, is undoubtedly an old-school Hollywood lothario. And his connection to Tinseltown’s greatest playboy does not end at a passion for attractive women.They both mixed with powerful people on yachts, had some reportedly strange bedroom antics, flew on private jets, promoted liberal politics – and their mere presence was seemingly enough to get women to throw off their clothes.Most read in CelebrityHere, Grant Rollings compares the Playboy empire founder and the ultimate movie playboy.Hugh’s widow Crystal herself says: ‘Leo DiCaprio is turning into the new Hef’Credit: RexLovers with an eye for a much younger girlfriendNO matter how much older Leonardo is or Hugh was, the women in the two men’s lives were rarely aged beyond their twenties.The actor is currently dating 25-year-old ­Italian beauty Vittoria. But the relationship is not expected to last because the lothario has a tendency to split from partners once they are older than a quarter of a century.Leonardo DiCaprio’s girlfriend Vittoria Ceretti goes braless under sheer top and strips off to lingerie and suspenders for sizzling shootAs Crystal said: “Oh God, Leo, it’s a bad look.”In 2022, Leonardo broke up with model Camila Morrone after four years when she turned 25. Gisele Bundchen was 23 when they ended, Bar Refaeli was 25, and he had a fling with Gossip Girl’s Blake Lively when she was 23.Crystal was 22 when she first dated Hugh, but she’d reached the ripe old age of 31 when he died seven years ago in his nineties.Prior to marrying his final wife, Hugh slept with over a thousand women, including many of the Playmates who posed naked in his soft porn mags. And yet he was more traditional than Leonardo because he tried marriage.There are no signs the womanising actor plans to walk down the aisle any time soon.After Titanic it’s claimed Leo tried Hef’s sex grottoA WHO’S who of United States fame have enjoyed the warm welcome of the Playboy ­bunnies at Hugh’s mansion over the past decades – including Leonardo.Shortly after 1997’s box office record- breaking movie Titanic transformed him into a global star, he was said to have tested the water of the fun palace’s notorious sex grotto.Guests swim underwater to the private spot, which is a secluded area of the pool made from artificial rocks.It contains a hot tub and several water beds, where scantily clad women lie enticingly.In 1998 it was reported: “DiCaprio and Hef disappear into it with girls and then they are gone for hours.”The same year, Hugh was invited to Leonardo’s 24th birthday bash and the favour was returned when the actor was a star guest at a New Year’s party at the mansion, alongside Cameron Diaz and Joaquin Phoenix.To this day, DiCaprio enjoys a champagne lifestyle, attending endless glamorous events and showbiz bashes.Their magic touch soon had ladies stripping offBOTH Hef and DiCaprio had a magical power that many men would envy – with women eager to go ­topless when they saw them.In order to appear in the pages of Playboy magazine, which Hugh started in 1953, the female models needed to impress the ­entrepreneur with their breasts.If they weren’t ample enough for his liking, it wasn’t unusual for him to ask them to have implants.Leonardo appears to be pretty relaxed with semi-naked women wandering around.In 2012, during a party on a yacht in Sydney, some models started removing their bikini tops as the star and his actor pal Jonah Hill enjoyed their company.Equally, he has had more than one ­encounter on set with female co-stars who have stripped off.For Barbie star Margot Robbie, her first “start-to-finish sex scene” was on The Wolf Of Wall Street with the movie hunk.Jetting to parties and star-studded list of palsTHE green credentials of Leonardo have been questioned ever since he was first spotted using private jets.He also once flew from one New Year’s Eve party in Australia to another in Las Vegas so he could celebrate twice that year.Hefner had his own private jet called The Big Bunny, which had a disco, an oval bed and leather sofas. Guests were served lobster and roast beef dinners by Playboy bunnies wearing the famous rabbit ears.Among those who flew with Hef were Frank Sinatra and Elvis Presley. But he sold the DC-9 jet in 1975 as his business took a nosedive.Leonardo has his own star pals, with Mick Jagger, LeBron James and Bradley Cooper all attending his 48th birthday party in 2022.He is a businessman, with his production company Appian Way making Oscar-nominated The Revenant and The Wolf Of Wall Street.But eyebrows were raised about his involvement with Malaysian businessman Jho Low, who helped to fund the latter movie and is alleged to have committed a £3.5billion fraud.Duo’s bedroom antics ‘did not live up to the hype’HEFNER and DiCaprio both have a reputation as world-class ladykillers – but there are rumours that their bedroom performances did not always match the hype.In 2016 a source who claimed to be a friend of one of Leonardo’s lovers said: “She told me that during the act, Leo put on headphones and even started vaping.“Then he signalled her to keep going while he just laid back and zoned out.”Crystal’s stud rating for Hef’s bedroom performances was even lower.In 2011 she said that sex with him was over in “two seconds”, and added: “I’m not turned on by Hef, sorry. He doesn’t really take off his clothes. I’ve never seen Hef naked.”Other former Playboy stars who had shared the tycoon’s bedroom described how it was full of junk, the bed was strewn with vibrators and porn was playing on a big screen.Some of them complained that he refused to wear a condom during intercourse and he admitted to needing Viagra pills before he could perform between the sheets.Liberal views on sex – and ‘right-on’ causesLEONARDO is famous for promoting worthy causes such as tackling man-made climate change.More surprisingly, perhaps, multi-millionaire businessman Hefner also had views that could be considered liberal.After he died in 2017, civil rights activist Reverend Jesse Jackson praised him for being a “strong supporter”.Hefner also gave financial support to the presidential campaigns of Democrats Barack Obama and Al Gore.READ MORE SUN STORIESHe spoke up in favour of same-sex marriage – and, less surprisingly, was all for liberal attitudes to sex.Leonardo has helped to produce documentaries about environmental issues and appeared at the United Nations Cop26 climate change conference in Glasgow three years ago.Crystal, 37, was 60 years younger than her three-times-married husband HughCredit: ReutersThe Oscar-winning actor was often said to be at glamorous events arranged by HughCredit: Getty More