Cameron Douglas, the wayward son of one of Hollywood's most star-studded acting families, fought back tears as a judge rejected a plea for clemency and nearly doubled his prison sentence for drug offences.
New York federal Judge Richard Berman ordered a sentence of four and a half years to be served after Douglas completes his current five-year sentence. The new sentence, for possessing drugs in jail, was double what even prosecutors had been asking for.
The 33-year-old son of Oscar-winning father Michael Douglas and grandson of screen legend Kirk Douglas bowed his head as Berman described his "reckless'' and "deceitful'' conduct and said he'd already been given his "last chance.''
Moments earlier, Douglas, who has inherited the famous jutting jaw and straight hair, worn swept back, of his father, begged for mercy, saying he wanted to concentrate on curing his drug addiction.
As he struggled not to cry, one of four relatives attending the hearing broke into sobs.
"I plead with you, Judge Berman, to grant me the opportunity to treat this malignant affliction,'' said Douglas, whose father is married to Catherine Zeta-Jones, another Oscar winner.
"I cannot seem to find comfort within my own skin. My mind is constantly seeking relief from itself,'' Douglas said, his voice catching as he glanced down at a green notebook.
Before the hearing, Douglas had sent Berman a two-page, handwritten letter speaking of his "shame and penitence that I have once again cheated my family and my loved ones,'' while insisting that if given a chance he could live "the rest of my life to the fullest".
His defence lawyer argued that Douglas, once an aspiring actor, had been addicted to LSD, methamphetamine, cocaine, heroin and other drugs for most of his adult life.
Having barely received treatment in prison, he had little chance of reforming his behaviour, however much he wanted to.
Douglas was arrested in July 2009 in a New York hotel with large quantities of methamphetamines and pleaded guilty to trafficking from California. He'd also been previously jailed in 1999 and 2007 on drug charges.
Despite promising to go clean, Douglas continued to secure supplies while behind bars, including with the help of a lawyer who hid the narcotics "apparently in her bra,'' Berman said.
Berman pointed out that when he sent Douglas to prison the first time, back in April 2010, he'd given him a sharply reduced five years, half of the potential sentence.
Berman said he'd told the court then that this had been "the last chance to make it".
"What's important is not to get warm and fuzzy. The rule there is pretty clear,'' the judge said.
Douglas's lawyer said his client needed help, not punishment. "Before the drugs and beneath the drugs, there's a good person,'' he said.
But Berman was not in forgiving mood.
"He seems to have blown the biggest opportunity of his life,'' he said.