Barry O’Keefe did not want his son Andrew to go into show business. The titan of Australian justice – he was a judge, mayor and corruption fighter – had watched helplessly as his younger brother Johnny, Australia’s first rock star, was consumed by drugs, booze and mental health problems, and died from a prescription drug overdose at 43 years old.

“He was disillusioned by the people who plagued Uncle Johnny and devastated by the death of his little brother, who died too young from the excesses of his crazy lifestyle,” Andrew once told a newspaper, well before his own excesses began to consume him, too. “[He] could see what the showbusiness lifestyle can do to a person’s health.”

Perhaps the elder O’Keefe saw echoes of his brother in his youngest son. Both blazed bright. They were skillful, creative and magnetic. If anything, Andrew’s potential was greater; he had all of Johnny’s charisma while also excelling academically. The young man felt the tension between those two sides of himself, the academia of his father and the showmanship of his uncle. A distinguished legal career lay ahead if he wanted it, but the lure of the footlights was strong.

The late Justice O’Keefe was right to be afraid. His son is in custody now, which is perhaps the safest place for him. A drug, violence and mental health spiral with uncanny similarities to that of his uncle’s 50 years earlier has sent him on a years-long odyssey of court hearings and holding cells and rehab centres and domestic violence charges and angry, defensive outbursts from the dock. Last weekend, despite at least10 attempts at rehab, he almost died of a heroin overdose.

Only O’Keefe can pull himself out of this mess now. “God help him,” Magistrate Jacqueline Milledge said.

Barry and Janette O’Keefe’s five children grew up on Sydney’s north shore with every material advantage. While rocker Johnny O’Keefe was nicknamed the “wild one”, his brother Barry was known as the “mild one”, as he advanced from barrister to Mosman mayor to Supreme Court judge to Independent Commission Against Corruption boss. He would have been an imposing father. He wanted his children to learn two instruments (Andrew is a classically trained singer and plays the trumpet). He sent them to private schools. The three boys chose law degrees when they left school.

As a kid, Andrew idolised the counterpoint to his father; his uncle, Johnny, who gave the boy a taste of showbiz before he died. Decades ago, in a profile to promote his Channel Seven game show Deal or No Deal, he remembered having so much Johnny O’Keefe merchandise that his cupboard was like a shrine. He still had a tape of a day when Johnny – who had his own Channel Seven show, Sing Sing Sing – announced his nieces and nephews as the next big thing, and they’d perform a song. “Ladies and gentlemen, Sydney north shore’s king of rock ‘n’ roll - A’OK, take it away!”

Schoolmates from St Ignatius college remember O’Keefe as a clever, charismatic student who was idolised by younger boys not just because of his abilities, but because he was kind. He played sport, shone on stage and was at the top of his class. He represented Australia in school-level debating. There is a photograph in the Herald’s archives of the paper’s 1989 Plain English Speaking Award, in which the finalists included a baby-faced O’Keefe and Michael Fullilove (now the executive director of the Lowy Institute, who won).

After achieving sky-high marks in the HSC and studying law at Sydney University (with stints as a department store Santa over Christmas), he worked in intellectual property at a top-tier law firm and indulged in his passion for the stage on weekends. In 2001, he won the world improvisation championships in Montreal. Two years later, he made the jump to full-time entertainment to work on Seven’s sketch show Big Bite with Chris Lilley (Summer Heights High) and Kate McCartney (The Katering Show).

In his interviews over the years, O’Keefe has spoken about the tension, within himself and within the family, over that choice. “I was overruled by the judge,” he said, when asked why he delayed his move to television for so long. In another interview, he acknowledged that the biggest problem with show business was that “it drives you mad, thinking and talking about yourself all the time”. He said his serious father and wild uncle were united by one personality trait; a single-minded drive to succeed. He later put it this way; the O’Keefe men possess a strong strain of “something that verges on mania”.

Still, with all his talent and charisma, the career switch was a success. At one point, O’Keefe was estimated to earn $1 million a year. He became a game show host, a co-anchor of Weekend Sunrise, and an occasional stage performer, including in his own cabaret show about his uncle. He had a penchant for Prada. He owned a tapestry by Arthur Boyd and an etching by Matisse. He was made a member of the Order of Australia for his television and charity work, which included chairing the anti-domestic violence organisation, White Ribbon. He had three children with his social worker wife, who he said kept him grounded.

O’Keefe once appeared in a short film, in which celebrities were asked to give their own eulogy. He said, “many complete strangers said Andrew was inveterately happy”.

The first public sign of problems came in 2008. A heavily intoxicated O’Keefe was filmed outside a Melbourne nightclub slurring his words, falling into the road, and lying in the gutter. Some teenagers filmed him; Seven scooped it up for $25,000 to stop anyone getting hold of it. But there was more video, which leaked. The interest was prurient, but most people dismissed the incident as an overly enthusiastic night out.

Yet O’Keefe’s troubles intensified over the following decade. His father died in 2014, and his marriage ended in 2017. He said those shocks were behind his euphemistically termed “emotional exhaustion”, which began a series of stints in rehab. By 2018, word was getting out that it wasn’t just fatigue. A tabloid magazine carried stories about 48-hour benders in which one witness reportedly described him as “clearly very wasted”. Rumours abounded that he was increasingly difficult at work. The Australian later reported his drug problems were so bad, he had to be escorted to the set and had an ice pipe in his dressing room.

When O’Keefe opened up to News Corp on this exhaustion and rehab stint in late 2019, in one of many attempts to stop the speculation, neither he nor Channel Seven acknowledged any substance abuse. He said he wasn’t treating himself well after his father’s death and marriage break-up, and that he got to a point where “I knew it wasn’t sustainable to work, to grieve, to feel pain and not to sleep so I took myself off to the clinic”. He’d be back in rehab again and again.

In 2021, as his spiral intensified, Seven cut ties. That year, he also admitted to spitting, slapping and kicking his new partner when she accused him of bringing an ice pipe to a party. The charges were dismissed under the mental health act after the magistrate accepted that O’Keefe had been in a hyper manic state, and there was evidence of bipolar disorder in the family. He also had substance use disorder. There was another incident that year in which he kicked, pushed and spat at a woman, for which he was found guilty in January this year.

There were more arrests and charges; so many that it’s difficult to pick them apart. He was arrested in early 2022 for allegedly punching, kicking and attempting to choke a potential business partner and former sex worker in a dispute over $20,000. Police said they found a highly toxic amphetamine while there, too (the charges were eventually dropped because the witness left the country). As he was driven between police stations, O’Keefe banged the police wagon and screamed at journalists. The tendency to blame others for his woes – the mark of an addict – was on display. “F--- you, I’m a victim of crime,” he shouted at waiting journalists.

That began his first spell in custody, in which he slept in a one-man cell. It was a far cry from the world of Prada and Matisse. He was given his only hot meal of the day – heated from a chill pack – and his overnight rations of milk, cereal and seven slices of bread before the cell was locked at 3pm. He told the court he was bullied by guards, but the guards told a different story. “He’s demanding. Constantly asking for this and for that … he’s a real prima donna,” one reportedly said. He was eventually given bail on the condition he attended a 12-month rehabilitation course.

That was rehab attempt No.10, at a waterfront facility north of Newcastle. O’Keefe has had more shots at it since then. He gave News Corp two glimpses of his life during that stint, one of them within a week of arriving in which he talked of addressing his issues “in a way that is very much focused on being a useful member of family and community”. He wanted to regain his practicing certificate and rebuild his relationships.

In the second visit by the journalist, he was reported to be rallying his “band of brothers” (including an alleged bikie boss and Matthew Ramsay, the high-flying real estate agent convicted of stabbing his best friend’s wife). Ever the showman, he is said to have jumped on stage and grabbed the microphone to congratulate graduates. “You are beautiful men, go well,” he said.

Loading

But he was back in court six months later, testing positive to ice and cocaine. The court visits appeared to accelerate. Then there was a charge of drug driving. Then an AVO breach. Then, this July, for allegedly driving with his licence suspended. Then, a few weeks later, for driving under the influence of drugs (he said the jacket in which police spotted an ice pipe was worn by someone else). Then, for allegedly stalking and intimidating his ex-girlfriend’s new partner, and breaching an AVO. The latest charge, which prompted Milledge’s comments, was for breaching his bail conditions, and possession of a prohibited drug. He was, the magistrate said, “lucky to be alive”.

The spiral has been devastating for his family. It’s the typical story of an inveterate addict, but played out on the national stage because of his celebrity. His mother, who comforted her husband after the death of his brother, is alive to witness the disintegration of her son. His two brothers and two sisters are witnessing it too, bracing for the headlines that appear ever more frequent. “It is so hard for us to have to watch this,” his sister Vanessa told the Daily Telegraph this week. Fifty years after Johnny died after years of drug and mental health problems, the O’Keefes are again watching the self-immolation of a son who shone so bright.

Start the day with a summary of the day’s most important and interesting stories, analysis and insights. Sign up for our Morning Edition newsletter.