Sean Penn
The Controversial Star: A famously combustible character, Penn has endured a fractious relationship with the press over the years, famously spending 33 days in jail back in 1987 after dangling a paparazzo off his ninth-story balcony. His stormy relationship with Madonna would blow up in similarly unsavoury circumstances, the star pleading to a misdemeanour charge after accusations of domestic abuse.
Lowest Ebb: The breakdown of his long-standing marriage to Robin Wright after a failure to control his burgeoning problems with drugs. Allegedly.
Errol Flynn
The Controversial Star: “I like my whiskey old and my women young,” claimed Flynn. Quite a pithy one-liner as it goes, although it becomes less funny in the wake of the statutory rape accusations that met him after WW2. No charges were brought however, and Flynn would go on to bring his brand of devil-may-care hedonism to the bright lights of Hollywood.
Lowest Ebb: These days the aforementioned scandal would stop an aspiring celebrity dead in their tracks, but in Flynn’s case it only served to enhance his reputation as a dashing womaniser. Hmmm.
Nick Nolte
The Controversial Star: A self-confessed hellraiser with a stormy personal life (three divorces and counting), Nolte finally came undone in 2002 when he was arrested on suspicion of drunken driving, only for tests to reveal he was under the influence of GHB. Nolte defiantly claimed, “I’ve been taking it for four years and I’ve never been raped,” before wisely checking himself into rehab.
Lowest Ebb: The accompanying mugshot, as seen above, tells a story to which no words could ever do justice. Put simply, the man appears quite deranged.
Winona Ryder
The Controversial Star: Drinking, drug-taking and sleeping around... these are the sort of misdemeanours we expect our celebrities to be getting up to in their spare time. But thieving? Well, that’s a little more out there. Still, that’s what happened when Ryder went for the old five-finger discount during a visit to Saks Fifth Avenue in 2001. Sadly for her, the whole thing was on CCTV...
Lowest Ebb: The fallout of the aforementioned scandal was conducted entirely in public, with Ryder sentenced to three years' probation, 480 hours of community service and some $10,000 in fines and restitution. Ouch.
Arnold Schwarzenegger
The Controversial Star: “Milk is for babies!” Who could have guessed that the oafish star of Pumping Iron would one day go on to become Governor of California? He even married a Kennedy for heaven’s sake! However, the glory days couldn’t last, and Arnie’s personal life would eventually explode in a fireball of lurid tabloid headlines. Wandering hands are one thing, but when you sleep with the maid, you’re pretty much screwed.
Lowest Ebb: It’s happening as we speak. Arnie’s extra-curricular activities with the home help appear to have cost him his marriage. That said, we’ve a feeling he’ll be back.
Gary Busey
The Controversial Star: Good old Busey has been a reliably erratic Hollywood presence throughout his long and illustrious career. An all-consuming cocaine addiction wasn’t helped by a motorcycle accident which resulted in mild brain damage. Naturally, he hadn’t been wearing a helmet.
Lowest Ebb: Having dropped a wrap of cocaine on the floor, Busey was horrified to see his dog rolling around in his precious powder. “I went in like a cropduster with my nose flying first,” he later explained. “I snorted the cocaine off the dog.” Bleurgh.
Lindsay Lohan
The Controversial Star: Having made her name in teen-friendly fare like Mean Girls and Freaky Friday , imagine parents’ dismay when wholesome, clean-cut Lindsay became wild-eyed, booze-addled LiLo. In and out of rehab, with a string of DUI charges hanging over her, Lohan finally wound up in jail in 2010, having failed a drug test and violating her parole. The textbook case of too much, too soon.
Lowest Ebb: The bizarre incident in February 2011, in which Lohan was accused of stealing a $2,500 necklace and placed under house arrest on a misdemeanour charge. Never a dull moment, eh Linds?
OJ Simpson
The Controversial Star: A celebrated NFL star turned up-and-coming actor, Simpson saw his career hit the skids in 1994 when he was charged with the murder of ex-wife Nicole Brown and her friend Ronald Goldman. Despite initially failing to turn himself in, the jury would eventually find Simpson not guilty in a trial watched by more than half the US population. Simpson would go on to be found liable for the couple’s unlawful death by a civil jury, ordering him to pay $33.5 million damages to the Goldman family. Unsurprisingly, his acting career never recovered.
Lowest Ebb: The release of ‘hypothetical’ memoir If I Did It: Confessions Of The Killer (with the word “if” printed in vastly smaller lettering) broke all boundaries of taste.
Charlie Sheen
The Controversial Star: Narrowly missing out on the top spot is the Warlock of Winning himself, Charlie Sheen. Whether lashing out at pesky studio execs (those who are forced to “lay down with their ugly wives and their ugly children and just look at their loser lives”), snuggling up to his duo of pornstar girlfriends or hoovering up heart-bothering lines of cocaine, Sheen is on a one-man mission to total meltdown. But remember, he’s not bi-polar. He’s bi-winning.
Lowest Ebb: His divorce from Denise Richards amid claims of alcohol abuse and threatening behaviour was followed by a similarly acrimonious split from Brook Mueller, with People Magazine reporting the actress had taken out a restraining order against the star. Way to go Chaz.
Mel Gibson
The Controversial Star: The undisputed king of Hollywood controversy, Mad Mel has ranted and raved his way from one row to the next as his career has unravelled spectacularly over recent years. Whether fending off domestic abuse accusations, drinking himself to oblivion or pursuing his ongoing battle with the Jewish faith, Mel is never short of people to offend with his bizarre and erratic outbursts.
Lowest Ebb: His DUI arrest probably tops the list, accompanied as it was by a string of racist abuse to the arresting officer. Claiming “the Jews are responsible for all the wars in the world,” Gibson took the remnants of his tattered reputation and promptly set them ablaze.
