The Clueless actress first met the British screenwriter when she was 17, but the pair didn’t start dating until 2006. The couple tied the knot the following year, which surprised many of Murphy’s family and friends, including her King of the Hill costar Kathy Najimy.
The HBO Max documentary What Happened, Brittany Murphy? takes a closer look at the troubled relationship between the pair, who died within two months of one another. In the two-part film, released in October 2021, Najimy said people in the Sin City actress’ life were “scared and freaked out” by Monjack.
“Like, who was this guy and what was happening?” the Hocus Pocus actress said in the doc. “She wanted to marry him, and I said, ‘Honey, it’s not been long enough.’”
Before saying “I do,” Murphy had been involved in high profile romances with her 8 Mile costar Eminem and Ashton Kutcher, who starred with her in the 2003 comedy Just Married. She was engaged twice, first to producer Jeff Kwatinetz for nearly five months in 2004 and again the following year, to Joe Macaluso, a production assistant on her 2004 film Little Black Book. The pair ended their romance in August 2006, shortly before she took up with Monjack.
While many seemed confused by the pairing, Murphy told OK Magazine in April 2009, eight months before she died, that “the easiest decision I ever made in my life was getting married.”
However, in the HBO Max doc, those close to the Girl, Interrupted actress describe Monjack as a sinister presence in her life. Alex Merkin, who directed Murphy’s 2009 film Across the Hall recalls seeing red flags in the Two Days, Nine Lives director. Merkin claimed he exhibited “Jekyll and Hyde behavior” and often seemed “out of it.”
The man at the helm of one of Murphy’s final films remembered the Georgia native coming to set and “be[ing] in a really good place, and then I would see her go off with Simon.” When she would come back, Merkin said he “felt a stark change in her mood.”
Following her death, many including Murphy’s father, Angelo Bertolotti, accused Monjack of having a hand in her demise — something the Factory Girl producer vehemently denied months before his own May 2010 death.
“Our marriage was dogged by these ridiculous rumors. Brittany’s life was dogged by ridiculous rumors, and the truth always wins out,” he told Us Weekly in February 2010. “I hope people have the sense to really understand that everything was beautiful and wonderful in our relationship and so pure.”
Keep scrolling to learn more about this tragic Hollywood romance.