Justin Timberlake allegedly cheated on Cameron Diaz with Playboy model

A former Playboy model has alleged she once shared a steamy night with Justin Timberlake at the mansion – while he was in an A-list relationship.

Former Playboy model Zoe Gregory claims she once hooked up with Justin Timberlake while the SexyBack crooner was dating Cameron Diaz in the early aughts.

The blonde bombshell, now 49, told the Daily Mail that she met Timberlake, now 43, at a party at the Playboy Mansion, and she was first to make a move on him.

Gregory claimed the Rock Your Body singer initially declined, stating he was dating Diaz, but when she further enticed him by saying the Charlie’s Angels star was “not with [him] now,” he allegedly gave in.

“He didn’t want to look like a wimp,” she told the outlet. “We both got in the grotto, and we both got our kit off — down to his shorts — and we ended up fooling around.”

The porn star clarified she and Timberlake did “not have sex,” but they allegedly fondled and “made out”, reports Page Six.

Justin Timberlake and Cameron Diaz.

Gregory claims she hooked up with him while he was dating the actress. Picture: Instagram

Page Six has reached out to his reps for comment but did not immediately hear back. Diaz’s reps also did not respond.

Gregory previously exposed another taken man with whom she allegedly had a tryst: Alex Rodriguez.

In 2019, she claimed A-Rod had sexted her just weeks before he proposed to Jennifer Lopez.

“He was being like a dirty dog. He seemed like a needy, horny bloke,” Gregory told the Sun at the time. “If he is doing this right up until the point he is proposing to her, it is just not fair.”

Timberlake’s dating record has not been squeaky clean either.

Britney Spears recently accused the Cry Me a River singer of cheating on her multiple times throughout their three-year relationship.

The Princess of Pop, 42, claimed in her best-selling memoir The Woman in Me, released in October 2023, that Timberlake had been unfaithful to her with “another celebrity.”

The former *NSYNC member was rumoured to have cheated with Nicole Appleton of the English girl group All Saints after they were spotted heading back to his hotel in London in 2000 — while he was still with Spears.

Spears claimed in her memoir that he also cheated on her. Picture: Tom Mihalek/AFP

It was also reported amid the pop icons’ romance that the Oops! … I Did It Again singer once flew into a “jealous rage” when she found Tonya Mitchell, an up-and-coming singer who had performed as one of *NSYNC’s opening acts, on her then-boyfriend’s bed, according to an archived Star magazine article.

Timberlake then broke up with Spears via text when he found out she cheated on him with choreographer Wade Robson.

Despite his own heartbreak, the What Goes Around … Comes Around singer has since been caught in more compromising situations.

Just a few weeks after his split from Diaz, now 51, in 2007, Timberlake was seen chatting up Jessica Biel at a Golden Globes party, which reportedly infuriated the actress. It’s unclear whether there was any crossover between those two relationships.

He’s now married to Jessica Biel. Picture: Matt Winkelmeyer/Getty Images

The Selfish singer dated Biel for some time, but in 2010 he was rumoured to have cheated on her with Olivia Munn. He denied the allegations at the time via his rep.

Sources claimed Munn, now 43, resisted his advances initially, but then gave in to a night of passion at her Park Avenue hotel, where the pair were “openly affectionate.”

Timberlake and Biel, 41, overcame that hurdle, going on to wed in 2012 and have two kids together.

However, in November 2019, the former boy band member was caught holding hands with his then-co-star Alisha Wainwright off-set while they were filming a movie in New Orleans.

Timberlake issued an apology shortly after, writing via Instagram in part, “A few weeks ago I displayed a strong lapse in judgement [sic] — but let me be clear — nothing happened between me and my co-star.

“I drank way too much that night and I regret my behaviour. I should have known better.”

This article originally appeared in Page Six and was reproduced with permission.

Originally published as Justin Timberlake allegedly cheated on Cameron Diaz with Playboy model