The extent to which an all-consuming grief went on to hasten the death of the 39-year-old Briton will perhaps never be known, but shortly before 10pm on Sunday night his mother-in-law Sharon entered the bedroom of his sprawling home in the Hollywood Hills and found him unconscious.
Paramedics, who were beaten to the scene by a team of firefighters, could do nothing to revive Mr Monjack and he was pronounced dead. Sergeant Louie Lozano, of the Los Angeles Police Department, said there were no suspicious circumstances and added that the preliminary cause of death was a suspected heart attack.
It was the final drama of an improbable and tortured life which began in Buckinghamshire's affluent stockbroker belt and ended, via a brief interlude as a wannabe art mogul for Damien Hirst, with a man best known as the portly consort of a pretty Hollywood actress and a scandal-prone also-ran in the ruthless world of movies whose dealings had – rightly or wrongly – earned him the nickname "Con-Jack".
For Sharon Murphy, whose daughter was the result of her short-lived marriage to an Italian mobster, Sunday night was full of unbearably grim repetition. On 20 December 2009, she entered the same bedroom in the house to find Brittany unconscious in the en-suite shower room, lying in a pool of her own vomit.
Mr Monjack, who had suffered a minor heart attack shortly before his wife's death and shared their split-level mansion with his mother-in-law, later described how he had tried in vain to resuscitate his wife before kissing her goodbye.
Linda Monjack, Simon's mother, who works as a self-employed hypnotherapist in the Buckinghamshire village where he grew up, described the nature of her son's grief, saying: "He has lost the love of his life... Some days he wants to kill himself, and other days he seems to be coping better. He is distraught. I speak to him every day, and he is often in tears."
An inquest found that Miss Murphy, 32, who joined the rota of Hollywood's leading ladies after her appearance in the 1995 hit Clueless, died from a cardiac arrest brought on by pneumonia complicated by iron deficiency, anaemia and multiple drug intoxication. Investigators found large quantities of prescription drugs belonging to her, but her husband insisted they were mostly out-of-date medications.
The coroner's verdict that the actress, whose film appearances had grossed £62m for Hollywood's studios, had died accidentally did little to diminish what followed. The LA rumour mill, supplemented by a host of prolific gossip websites such as TMZ.com, declared open season on Mr Monjack's reputation.
Rumours were rife in cyberspace that the Briton was implicated in his wife's death, while the mainstream media gave vent to allegations that, burdened by debts from a string of disastrous film deals, he had used his "famous charms" to lure Miss Murphy into marriage and use her fortune to pay off his creditors.
He angrily denied the claims, and there was never any evidence that the death of the actress, whose film credits included 8 Mile and Just Married, was the result of anything other than her constitution, weakened by a dependency on a cocktail of medications and an apparent eating disorder, succumbing to a life of excess and an opportunist virus.
But Mr Monjack, by his own admission, had enough question marks over his past to sustain the suspicion that he was a silver-tongued chancer billing himself as a "screenwriter, director and producer" who had covered up his transgressions and inflated his achievements (his sole directing credit was for Two Days, Nine Lives, a 2001 low-budget British film starring Luke Goss) in the hope of being taken seriously in Hollywood.
His nickname came from a series of financial scrapes, including the filing of credit card fraud charges against him in Virginia in 2005; his eviction from four homes; a lawsuit by Coutts, the Queen's bank, successfully suing him for $470,000 (£326,000); and a divorce settlement dating back to 2001 that was only settled in 2009.
A former business acquaintance of his said yesterday: "Simon is someone who I suspect went through life with genuine intentions of making his various schemes work and then being reluctant to shoulder the blame when they didn't. He wasn't bad. But he was chaotic and he liked to make the most of anything he had done. He was interested in photography, so he would tell people he had taken pictures for Vogue."
Mr Monjack answered the allegations against him with the classic weapons of the wronged rogue – candid admission and a claim that he was the victim of a shadowy elite.
Speaking after his wife's death, he said: "I know I have been called a conman. I am not perfect. I never said I was. But there has been so much rubbish written about me and Brittany. Most of what you read is made up. My problem is that I do not look like Ashton Kutcher [a former co-star and boyfriend of Miss Murphy]. Nor do they like the fact that she married someone who was not famous. Here, stars like to marry other stars."
Raised in the north London suburb of Hillingdon and then the salubrious Home Counties village of Bourne End, Mr Monjack hailed from the upper echelons of the English middle class. His mother ran her own interior design business and his father, William, worked in the City before dying from a brain tumour.
Mr Monjack, who lost his father at the age of 15, began his subsequent career in the arts claiming a fortune based his own dabbling in currency and derivatives markets.
He also displayed a talent for inflating his success, telling friends that he was one of the founders of the BritArt movement, was a close friend of Damien Hirst and had bought "150 to 200" paintings after funding the artist's first major show. He boasted that the subsequent collection was worth at least £200m. A representative of Mr Hirst told The Independent that Mr Monjack had put some money into an early show, In and Out of Love, but never met the artist. He owned a single "pill" painting which was sold soon after it was purchased.
The filmmaker was not without talent. He directed an advert for Nike's shoe range featuring the basketball player Michael Jordan. In 2006 he appeared to be on the threshold of a major breakthrough, announcing that he had secured funding to make The White Hotel, an adaptation of the acclaimed novel by DM Thomas about an opera singer in post-World War One Vienna who seeks the help of Sigmund Freud.
After initially offering the lead role to Nicola Kidman, Meryl Streep and Barbara Streisand, the film's backers announced they had secured the services of another star – Brittany Murphy. While the project ultimately foundered, romance blossomed between the putative director and his leading lady, who he first met when she was a teenager.
Amid claims, fiercely contested by Mr Monjack, that he was facing deportation from America because of visa irregularities, the couple married after an unannounced engagement in May 2007 at a private Jewish ceremony in their home.
Miss Murphy said in a magazine interview: "We first met when I was 17 years old. We checked in with each other throughout the years and remained friends. The easiest decision I ever had in my life was getting married. He's flown around the world to make sure we spend every single night together."
Not all friends of the actress shared her joy. George Hickenlooper, the director of Factory Girl, a biopic about Andy Warhol's muse Edie Sedgwick, said he had tried to warn Miss Murphy off her relationship with the Briton after the two men fell out over Mr Monjack's claim to have written an earlier script for the film.
It was amid such showbiz trench warfare that Mr Monjack entered what turned out to be final months of his life, feeling obliged to launch his own PR counter-offensive at a time when others might have expected him to maintain the silence of a grief-stricken widower.
Shortly before his own death, he invited a camera crew from a celebrity website to film a tour of his home,. As reports began to emerge last night that the Briton had died of a drug overdose as much as a broken heart, an interview filmed with Mr Monjack earlier this month was posted on the internet.
He told the cameraman: "We have got to the point in this culture where facts and fiction no longer matter. It is what you can get the average person to read. I think I had better stop there."
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