Jan. 20, 2010 -- What went wrong between Dennis Hopper and Victoria Duffy-Hopper? Those close to her wonder if the terminally ill actor's estate might be the reason he filed for divorce -- from what may be his deathbed.
"It's just so screwed up," a friend of Duffy-Hopper's family told ABCNews.com. "Maybe it's a money thing."
The friend suggested that tension between Duffy-Hopper and Marin Hopper, Dennis' oldest daughter from an earlier marriage, might have led the actor to move to end their nearly 14-year marriage. The friend also noted that Marin Hopper has been spending significant time at the Hopper compound in Venice, Calif. with her father and Duffy-Hopper.
"Marin is there at the house with them now, as I understand, and [Hopper] apparently wanted her to become the executor of the will," the friend said. "If he's dying in the next four weeks, what good is this going to do? It must be the money."
In October, manager Sam Maydew announced that Hopper, 73, was undergoing special treatments at the University of Southern California to battle advanced prostate cancer. Hopper's condition has reportedly worsened dramatically in recent weeks.
So it came as a shock -- not only to the public but also to those close to the actor and his wife -- when he filed divorce papers in Los Angeles Superior Court Jan. 14, citing "irreconcilable differences" with Duffy-Hopper, 41, and asking for joint legal and physical custody of their 6-year-old daughter, Galen.
"I wasn't aware of any problems," another family friend told ABCNews.com. "This was all a surprise to me. They came to visit us two years ago, and nothing seemed to be disturbing. Everything was just absolutely fine."
The friend said the couple had traveled around the country in July and "nothing seemed out of whack."
As for the their split, the friend said, "I have no clue what happened. Nobody has a clue," adding that in the wake of Hopper's filing, Duffy-Hopper "never answers her phone anymore. She's not talking to anyone."
Another friend of the couple told the Huffington Post that cancer medications have addled his mind.
"The poor guy has no idea what is going on," the friend said. "Even his lawyers are telling people he is on painkillers and is essentially sleeping all the time."
In a statement quoted by Reuters Monday, Hopper said, "I wish Victoria the best but only want to spend these difficult days surrounded by my children and close friends," while daughter Marin Hopper said, "Dennis is brave, and he is fighting a hell of a battle."
Representatives for Hopper did not immediately respond to requests from ABCNews.com for comment.
Hopper's History of Broken Relationships
While Hopper's divorce may seem shocking given his failing health, the actor is no stranger to marital woes. Duffy-Hopper is his fifth wife; perhaps unsurprisingly, he has history of rocky relationships.
In 1961, Hopper, then a rising star, met and married Brooke Hayward, daughter of the great Broadway producer Leland Hayward in New York. Brooke bore Hopper's first child, Marin, before they divorced in 1969, reportedly because of his hard-partying habits. Glenys Robers, a writer for Britain's Daily Mail, claims that in those days, he was into a number of drugs, including LSD, heroin and cocaine. According to Reuters, Hopper broke Hayward's nose during a drug binge.
The following year, in 1970, Hopper wed Michelle Phillips of the Mamas and the Papas. Their union lasted a grand total of eight days. Phillips later told Vanity Fair that she was subjected to "excruciating" treatment while with the actor.
Two years later, Hopper wed Daria Halprin, a dancer and actress in a handful of '60s and '70s films. The couple was married for four years and had one child, Ruthana Hopper.
Hopper had another marriage -- to television actress Katherine LaNasa, from 1989 to 1992, which resulted in a third child, Henry Hopper -- before settling down with Duffy-Hopper in 1996. Their 14-year relationship was by far the most solid one the notoriously unstable actor has ever been in.
Women aren't the only ones who have felt Hopper's wrath. In 1999, actor Rip Torn sued him for defamation after Hopper said, on "The Tonight Show With Jay Leno," that Torn pulled a knife on him back when they were getting ready to shoot the 1969 film "Easy Rider." Torn claimed that, in fact, Hopper pulled the knife. Torn won the case after a judge ruled in his favor, and Hopper was ordered to pay $475,000 in damages. When Hopper protested and appealed, the judge hit him again, ruling in the defamed actor's favor and forcing Hopper to pay another $475,000 in punitive damages.
Dennis Hopper's Colorful Career
The Kansas-born Hopper has had a colorful career in Hollywood. He shot to fame with "Easy Rider" in which he served as both star and director. Before that, he had acted alongside James Dean in "Rebel Without a Cause" and "Giant." In 1979, Hopper appeared in "Apocalypse Now" and in 1994, "Speed." His more recent work includes the role of record producer Ben Cendars in the cable TV series "Crash."
In addition to his film and television projects, Hopper has been a photographer, painter and sculptor. In 2001, Amsterdam's Stedelijk Museum displayed more than 100 of his works dating back to the mid-1950s. At the time, Hopper said the exhibit was his most significant achievement to date.
"It is the most important thing that ever happened to me, to be here at this museum," he said, according to the BBC. "That is serious, this is not about making 'Easy Rider,' it is about making these paintings. That is much more important to me than anything else that has ever happened in my life."
ABC News research associate Melissa Lenderman contributed to this report.