HOLLYWOOD — He was born into one of Hollywood's most celebrated families. But in his last days, Chris Penn was still hustling for his big break, dreaming up a movie he could direct, writing the screenplay and building the set with his own hands.
In his downtime, he'd while away the hours on his favorite perch — a stool at the far end of the bar at Locando del Lago, an airy Italian restaurant on Santa Monica's Third Street Promenade.
By early evening, his friend Phil Ursino, a cigar-smoking sometime actor with an old gold Lincoln, would often ferry the actor back to his Ocean Avenue condo packed with war props for his movie, a "Deer Hunter-esque" Vietnam film that he'd wanted to make for two decades.
He would work late into the night writing and fiddling with equipment. In the morning, friends said, he would load his truck with supplies and head up the coast to a canyon property owned by his more famous brother, Sean. Aided by a few day laborers, he would go to work constructing the set.
"He was sick with the flu, he was overweight, he was working all day and all night," said one longtime friend, Don "The Dragon" Wilson, a former kickboxing champion turned actor. "I was worried he was burning the candle at both ends."
Finally, at age 40, Penn's heart gave out. His housekeeper found him dead in his bed Jan. 23.
On Feb. 13, the Los Angeles County coroner's office ruled that he died of "cardiomyopathy," compounded by the use of "multiple medications."
For years, even as he gained a certain cachet as a promising and underrated actor, Penn fought to overcome cocaine and alcohol abuse while packing on more and more weight.
As his life moved on the dual tracks of work and addiction, Penn remained a popular figure in Hollywood circles and outside the industry — a very down-to-earth guy despite his family pedigree. Even so, he wanted to be doing better, sometimes pushing himself beyond his physical limitations.
"He'll be missed," Wilson said.
Wilson, who met Penn in 1984 when he was studying martial arts with a mutual friend, said Penn had been in rehab at least once. He kept a book on AA in his condo, said Wilson, who said he had once been Penn's roommate.
He would be fine for a while, Wilson said. And then something would trigger a relapse. Between 1987 and 2000, he racked up arrests for carrying a handgun, reckless driving, two DUIs and driving on a suspended license, according to court documents. His weight topped 300 pounds.
In 1996, he told London reporter Ben Thompson of the Independent that he had become addicted to drugs after the death of a baby he had fathered with a girlfriend.
"I started to play around with [drugs] a little bit, and then I had a tragedy happen," he told Thompson. "I lost a daughter — she was only 2 days old, she was born premature and her lungs were just too weak — and I went kind of overboard. I just used it as an excuse to do as many drugs as I could.
"It took me a year or so to figure out what I was doing, and by then I was completely addicted."
Wilson said Penn had talked to him about the loss. "He tried to verbalize it to me a couple of times," Wilson said. "It had a huge impact on his life. He was preparing to be a father, and all that was taken away from him in one tragic moment."
He tried to get his life back on track through work. His late father, Leo, was a blacklisted actor-turned-TV director, and his mother, Eileen Ryan, is an actress with numerous television and movie credits. His oldest brother, Michael, became a musician and married singer Aimee Mann. And then there was Sean, an Oscar-winning actor who was once married to Madonna.
Going into show business seemed natural for Chris Penn, who grew up making amateur movies at his family home near the beach in Malibu.
He made his acting debut in Francis Ford Coppola's "Rumble Fish" in 1983. Then he played one of Tom Cruise's pals in "All the Right Moves." More roles quickly followed: He was the awkward kid taught to dance by Kevin Bacon in "Footloose," he worked alongside brother Sean and Christopher Walken in "At Close Range," and he played the dogged detective pursuing a star-crossed couple in Tony Scott's "True Romance."
Some say he was most memorable as Nice Guy Eddie Cabot, alternately funny and deranged, in Quentin Tarantino's breakthrough film, "Reservoir Dogs."
As he became known as a character actor, Penn longed to be a leading man. He figured he had lost his chance because of his weight. "I'd never stop playing character roles, but I regret missing parts that I could have got if I'd been slim," he told the Guardian in 1997.
Two weeks ago, a number of A-list celebrities turned out for Penn's funeral at Holy Cross Cemetery in Culver City. There was Sean along with his actress wife, Robin Wright Penn, along with Jack Nicholson, James Gandolfini, Charlie Sheen and Tim Robbins, Wilson said.
By the end of his career, he had appeared in nearly 80 movies and television shows. Several movies are still to be released, including "Holly," a film directed by Guy Moshe in which Penn plays the head of an Asian crime organization, and Damian Lee's "King of Sorrow," a love story about a suicidal psychiatrist and a drug-addicted homicidal cop.