Justin Timberlake’s playboy past unpacked amid hand-holding scandal

Justin Timberlake was once dubbed “Trousersnake” for his ­conquests with a bevy of A-list women. Could he be returning to his old ways?

He was the playboy singer dubbed “Trousersnake” for his ­conquests – before he transformed into the squeaky-clean prince of pop with a film-star wife.

Now shock pictures of Justin ­Timberlake holding hands with his stunning new co-star on a boozy night out have caused quite a stir for the married dad-of-one.

RELATED: Who is Alisha Wainwright, the woman holding hands with JT

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Witnesses say the 38-year-old Cry Me A River singer appeared to have been drinking heavily as he cradled Alisha Wainwright’s hand in a bar in the city of New Orleans, where they are filming sports movie Palmer.

Wainwright put her hand affectionately on Timberlake’s knee. Picture: Mega.

At one point, Justin is said to have grabbed the 30-year-old actress’s hand and placed it on his bare knee, through a hole in his ripped jeans. He then caressed it with both his hands.

Though he had been snapped earlier in the week wearing his wedding ring, he did not appear to be wearing it in the new shots, which were taken as his wife of seven years, Jessica Biel, was 1,800 miles away in Los Angeles.

Justin was seen smiling and locked in conversation with his co-star, who plays his lover in the movie drama and is believed to be single. The pair were on a night out with other cast and crew members from the film.

In footage from the night, Timberlake played with his co-star’s hand. Picture: Mega.

Justin has since been photographed looking glum and dishevelled in a hoodie, with both hands in his pockets.

One insider insisted yesterday: “There is absolutely nothing going on between them. They are just working together.”

Florida-born Alisha, who began her acting career on YouTube ­comedy channel Smosh in 2012, is best known for her role in Netflix series Raising Dion, as well as US cable TV drama Shadowhunters.

Alisha’s rep insisted there was “no validity” to the speculation about her and Justin yesterday.

Alisha Wainwright is known for starring in Netflix series Raising Dion. Picture: Getty Images for Netflix.

But those close to him and Jessica — who have a four-year-old son, Silas — expressed concern.

A second source told The Sun: “He’s certainly playing with fire by getting so openly close to Alisha — whatever his explanation.

“Jessica may look like a soft touch but she’s feisty and extremely ­attentive about her and Justin’s image. Fans love him as a hot, squeaky-clean dad.”

A source told The Sun: “This has come as a shock. Justin and Jessica are not just seen as one of the tightest couples in Hollywood, but actually behave like it in private.

“Their relationship is considered one of the most stable in the business, although there have been a few bumps. Jessica has had to adjust to being a mum to Silas, stepping back at times from her career, while Justin has essentially carried on moving ­forward with music and films.”

They continued: “When Justin was single, he lived a life many people would not be able to imagine, with offers coming in from women all the time.

“But since his marriage and becoming a dad, there was a real change in him.

“His world was all about ‘his little man’ and in social groups he always praised Jessica for managing to raise their family while keeping their romance on track too.

“If this transpires to be something greater than a moment of friendship between Justin and his co-star, then Jessica will be heartbroken.”

Sources say Jessica would be “heartbroken” if it was more than just a boozy night between friends. Picture: Instagram.

Justin and Jessica met at a mutual friend’s birthday party in 2007, where he got her phone number from a pal and asked her out.

Only last year, Jessica, now 37, shared a picture of them on Instagram and said: “A picture says a thousand words. And thank goodness because there aren’t enough to express ALL the aspects of my love and respect for you.”

She may well find it easier to come up with words to describe him now.

Justin became a teen pin-up after joining boyband NSYNC in 1995 when he was just 14. In 1999 he began dating fellow teen pop star Britney Spears — his first love.

Timberlake’s hit Cry Me A River was reportedly written two hours after he split from Spears. Picture: WireImage.

They split after she reportedly cheated on him, and Justin was said to have never recovered from the heartbreak.

Just two hours after their break-up he wrote Cry Me A River, a song which would help to launch his solo career.

The song was included on his first solo album, 2002’s Justified, which sold more than ten million copies and brought him more mainstream success.

In 2003, Justin — who has won ten Grammys — was crowned the world’s sexiest man as his solo career skyrocketed.

High-profile relationships with actresses Cameron Diaz, Kate ­Hudson, Scarlett Johansson and Alyssa Milano followed.

Then in 2007 he began dating Jessica, who had enjoyed early ­success in films The Texas Chainsaw Massacre and The Illusionist.

After being snapped together on a visit to Britain, they went public with their romance in May of that year.

Early in the relationship, Jessica is said to have sent an email to her production partner saying: “I will marry this man.”

Biel was convinced early on that Timberlake was “the one”. Picture: AP

The pair survived cheating rumours — including claims that Justin bedded American actress Olivia Munn, which he strongly denied — before briefly splitting in 2011.

But just two months later they were back together and in December that year, Justin proposed.

They married in 2012 in Puglia, Italy, with Jessica appearing in a pink dress walking down the aisle to a song by Justin.

Three years later, in April 2015, their son Silas Randall was born.

Timberlake and Biel married in 2012. Picture: Getty.

Both have been vocal about their love during interviews and often post gushing social media messages about each other.

Justin has previously said: “Every once in a while, I can catch a glimpse of her when she doesn’t see me looking. I have this moment where I’m like, ‘If you only make bad decisions for the rest of your life, you made one really good ­decision.’”

During their early years together, Justin focused on his acting career, then in 2013 he returned to music and has now sold more than 32 million albums worldwide.

Meanwhile, Jessica’s film career took a back seat to focus on family life.

In March 2016 she launched child-friendly restaurant Au Fudge in Los Angeles but it closed two years later amid financial woes.

Our source said: “It was thought that Justin supported her through that low point and they successfully managed to balance their careers with staying close and raising Silas.

“That’s no mean feat, given how they were dragged around the world with their projects. Justin managed to jet home or have them visit him while on tour last year and by this spring everything was seemingly in good shape.”

In recent years, Jessica has returned to her film career, moving into producing.

In 2017 she was the star and executive producer of hit US TV crime series The Sinner and is now appearing in American ­podcast drama Limetown.

This article originally appeared on The Sun and was reproduced with permission.