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 the 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.