man in black shirt beside woman in black shirt

Matt Damon

Damon was born and raised in Massachusetts, and at the age of 10, made a new friend that would change the course of his life: Ben Affleck.

The two boys were inseparable from the moment they met and did absolutely everything together. They attended the same schools, on the same baseball team, and even played Dungeons and Dragons together – although that’s a side to their youth they’d probably rather we forget.

Affleck and Damon even have the same film to thank for kick-starting their careers: Good Will Hunting. The attention this Oscar-winning movie brought Matt led to his casting in films like Saving Private Ryan, The Talented Mr. Ripley, and The Bourne Trilogy.

The final film in that trilogy – The Bourne Ultimatum – also made Damon a record-breaker, when it had the most successful August opening weekend on record.

These day’s Damon gets to take his pick of the Hollywood roles – whether it’s dramas like The Monuments Men, Science Fiction films like Elysium and Zero Theorem, or heart-warming family films like 2011’s We Bought A Zoo. He even played Scott Thurson – Liberace’s boyfriend – in 2013’s critically acclaimed Behind the Candelabra.

Damon’s also tried his hand at TV comedy, with a recurring guest role in smash-hit sitcom 30-rock. He played Carol – Liz Lemon’s airline pilot boyfriend – and received rave reviews from the critics.

Back in 2008, Matt Damon appeared in a comedy music video for a song written by Sarah Silverman called ‘F*@#ing Matt Damon’. Silverman’s boyfriend Jimmy Kimmell played the video on his own show, and the clip went viral – with all three getting an incredible amount of media attention in the process.

Poker Pro

Success hasn’t changed Damon and Affleck – they still do everything together – and that includes playing poker.

Unlike Affleck, Damon doesn’t take part in nearly as many televised tournaments, but they are both regularly pictured in various Vegas best-known casinos and have also both been associated with a number of illegal high-stakes poker games in the past.

It may well be his appearance in John Dahl’s 1998 film Rounders that got Matt Damon hooked. In that film, he plays a gifted poker player who loses $30,000 in an illegal underground game. He vows never to play again – until he gets sucked back in while trying to help out an old friend.

Damon took up poker as research for the role – and lost a reported $25,000 of his own money in the process. Hopefully, his gains in the movie business have since made up for it.

Charlie Sheen

Son of acting veteran Martin Sheen – Charlie made his own on-screen debut at just 9 years old, as an extra in one of his dad’s TV movies.

Throughout his teenage years, Charlie worked with Sean Penn and Rob Lowe (then, just as unknown as he was) to produce and direct low-budget movies – a hobby that got him kicked out of high school, as he was too busy making films to attend class.

In 1984, Charlie finally managed to follow in the footsteps of his father with his first silver screen role – in Red Dawn. This eventually led to what he’s since referred to as a career-defining casting – as Chris Taylor in Oliver Stone’s 1986 Oscar-winner Platoon.

From there, the only way was up – with roles in Wall Street (a film that shone a light on the incredulous characters long before Leonardo DiCaprio’s ‘Wolf of Wall Street’), Navy SEALS, and the Hot Shots series placing Sheen firmly on the Hollywood hot-list.

In 2003 Charlie began work on Two and a Half Men – the sitcom about a bachelor with too much money and nothing to do with it but date an endless stream of beautiful women – whose life gets turned upside down when his brother and nephew move in. Sheen was paid a massive $1.8million for every single episode – which at the time made him the most expensive actor in Hollywood.

Bi-Winning?

This accolade went straight to his head and took its toll on Sheen – who allowed his problems with drink and drugs to spiral out of control. In 2009, he reportedly assaulted his wife – and went to rehab for 30 days. Just a year later, he was again arrested after causing damage valued at over $7,000. Reports at the time suggest he was under the influence.

By 2011, Charlie’s problems were no longer just wreaking havoc in his personal life – they were also having an effect on his career. A fallout with Chuck Lorre, the creator of Two and a Half Men, led the studio to suspend production. Sheen was eventually replaced with Ashton Kutcher.

At the time, Sheen took part in a number of TV interviews in which he seemed rambling and incoherent, yet headstrong and convinced by delusions of his own grandeur. It looked for a moment like an end for Charlie Sheen’s career, but in 2012 he was already back on our screens in yet another sitcom – the aptly titled ‘Anger Management’ on FX.

These days, Sheen considers himself a ‘retired gambler’, but in his heyday, he loved nothing more than a regular flutter. One of his ex-wives has claimed he used to spend $200,000 a week in the casino. Sheen’s biggest wager though was in 2008 – he bet $1million on Oscar De La Hoya to beat Manny Pacquiao. He lost.

Pamela Anderson

Like so many models, Pamela Anderson’s career started by chance. While working as a fitness instructor, she happened to be watching a football game wearing a tight ‘Labatt’s beer’ t-shirt – and found herself being broadcast on the stadium’s screens.

A representative of the beer brand saw her up there – and soon after, tracked her down. She appeared in the company’s TV adverts the very same year. She was soon being courted by Playboy magazine too – and appeared in a total of 5 issues.

Pamela always saw modeling as a way into a more lucrative career – and thanks to her newfound profile managed to pick up a number of small TV parts, including a recurring role in Tim Allen’s sitcom Home Improvement.

When the Producers of Baywatch found themselves in need of a new blonde bombshell to replace the departing Erika Eleniak, Pamela was seen as the perfect fit – and despite the series being panned by reviewers, the addition of Anderson and her red figure-hugging swimsuit helped Baywatch become the most-watched TV Show in the world.

As CJ Parker, Pamela Anderson was the world’s new favorite pin-up – and the iconic show still has cultural cachet today. The plot of Sacha Baron Cohen’s hit film Borat is built around the Kazakhstani character’s obsession with CJ, and his determination to meet her – and Pamela herself even has a cameo in the film.

But Pamela’s own big-screen career didn’t go so well. Despite her appearing in Cannes dressed in a revealing skintight leather catsuit to help with its promotion, her debut film Barb Wire was a failure – both critically, and commercially.

Paying Poker Debts

In 1995 a sex tape of Pamela Anderson and her husband Tommy Lee, made on their honeymoon, was stolen from their home and leaked online. One of the very first celebrity sex tapes, this paved the way for the many more that followed in its wake – and helped keep Anderson in the public eye, albeit for all the wrong reasons.

Pamela is known for her love of gambling, and is a regular on the slots in Vegas – but it’s long been rumored that Anderson has occasionally paid her debts with the one thing most Baywatch fans spent their teenage years dreaming about. Her body.

Back in 2007, after running up a huge poker debt of $250,000 in Las Vegas Casino, it has been claimed that Pamela offered her opponent Antonio Esfandiari a night of passion as a way to pay what was owed. Sources close to Anderson have – of course – insisted that these claims are untrue.