Tragic Details About James Caan

Actor James Caan died on July 6, 2022, leaving behind a plethora of iconic roles and a larger-than-life persona, per CNN. His most famous role was Sonny Corleone in the 1972 classic "The Godfather," which made use of Caan's own wild card-like personality. It would be a disservice to Caan to limit his legacy to a famous role, though, no matter how timeless it is, when Caan's private endeavors are enough to inspire its own movie. Born in 1940 to Jewish immigrants in the Bronx, Caan faced an inevitable future as a kosher butcher alongside his father so he found refuge in acting. Meanwhile, he pursued a variety of hobbies that only Caan would: boxing, bull-riding, motorcycle-riding, and roping as a heel in a rodeo (via the Los Angeles Times).

Caan's roles ran the gamut of rugged masculinity. One of his earliest roles was alongside John Wayne in Howard Hawks' "El Dorado" before portraying an NFL player in the hugely popular TV movie "Brian's Song." He also starred in James Toback's "The Gambler" and Richard Attenborough's "A Bridge Too Far," per CNN. Read on for several tragic details about James Caan.

Sonny Corleone ended up defining James Caan, but it didn't help that, not unlike his character, he was a little wild. He's done drugs, been married various times, and famously established a residency at the Playboy Mansion. Since he was a kid, he actively engaged in what he called "non-Jewish activities," which included boxing, bull riding, and getting himself into trouble. Because of his public image and aided by his real-life persona, studios were keen to pigeonhole him into a traditional masculine role, per The Independent. For example, he played a metastasized version of Sonny in Michael Mann's 1981 "Thief." He went on to play similar masculine roles in "The Gambler" and "The Killer Elite."

In an interview with The Independent, Caan bemoaned the lack of choices he was given. He was either "Mister Tough Guy or Mister Hero." Although that might seem like a great problem to have, Caan thirsted for something more challenging.

James Caan was married and divorced four times. His first marriage was to Dee Jay Matthis in 1961, which happened around the time when Caan's career got rolling. He wasn't yet a star, but he was surely on his way there. They had a child, Tara, and they divorced in 1966. His second marriage was to Sheila Ryan, a Playboy covergirl and Elvis Presley's ex-girlfriend. Together, they had Scott Caan, who later became an actor. They divorced in 1977, less than two years after marrying. Caan's third marriage was to model Ingrid Hajek in 1990. They had a son, Alexander James Caan.

The fourth time was nearly the charm. Caan and Linda Stokes, an actress and costume designer, married in 1996, and their marriage lasted 10 years. However, there were signs of trouble before it officially ended. Caan filed for divorce three times — the first two filings were eventually canceled by him, per Closer Weekly. The divorce itself was also messy. Caan had to hand over $400,000 over to Stokes for retroactive spousal support and $5,000 a month until she remarried, per TMZ.

If there was a role that would've won James Caan an Oscar, it was Sonny Corleone in "The Godfather." That was his sole Academy Award Nomination, per IMDb. Alas, the award went to the guy in "Cabaret," and Caan was left without an Oscar for the rest of his career which became a source of regret in his later years. In an interview with The Independent, Caan admitted to really wanting an Oscar at 80 years old and being bitter about it. He comforted himself by knowing that anyone who played a cancer victim was an automatic winner.

Caan believed that his real-life persona and public image became a distraction for Academy voters. Members of the Hollywood Foreign Press Association were more concerned about his sex life than they were about his acting, and asked him questions to that effect. They kept up on the latest tabloids, and so Caan's celebrity eclipsed all else. But even Caan's co-star Al Pacino stood no chance for an Oscar. That year, three actors from "The Godfather" took up Supporting Actor nominations, including Robert Duvall, likely splitting the votes between them. Pacino even boycotted the ceremony since Marlon Brando received the Best Actor nomination, not him. Caan agreed that Pacino's demotion made no sense, per The Independent.

Not finding the roles he wanted, James Caan decided to take matters into his own hands. He wrote and directed the 1980 family drama "Hide in Plain Sight." It was a film about a father who discovered that his ex-wife and their children had entered a witness protection program. The film, which was based on a true story, followed the father's search for his family, who were being hidden from a mafia. Film critic Roger Ebert gave it two stars and said it lacked quality screenwriting and direction. It had a limited release and only grossed $3.8 million at the box office, per IMDb.

But Caan believed in its potential and blamed the studio for its lack of impact. An executive at MGM and the head of the film's distribution company, United Artists, didn't share Caan's vision. The exec kept giving him notes and questioning his directorial style. Because the film had no sharks in it — a likely reference to the mega-hit "Jaws" — Caan said, "[Those] two idiots over at MGM didn't know what to do with it," per The Independent. "Hide in Plain Sight" opened to little fanfare. It received good reviews, but by then it was too late. He called the film one of his "great disappointments" and comforted himself by the warm response from his friends, which included Dustin Hoffman, per Rolling Stone. Even Francis Ford Coppola told him it was among his five favorite films at that time.

With the lack of varied roles and type-casting, along with the disappointing release of his directorial debut, James Caan began to feel frustrated by the film industry. After "Hide in Plain Sight," which reinforced his view that money, not quality, drove the industry, Caan starred in Neil Simon's 1979 movie "Chapter Two." But the marketing pushed Caan aside and put the spotlight on his co-star instead — Marsha Mason. He felt betrayed by producer Ray Stark and Simon, whom he felt underestimated his intelligence. 

Caan was vocal about the directors he didn't like. He and Alan J. Pakula, who directed him in "Comes a Horseman," didn't mesh well together, and Caan compared the filmmaking experience to prison, per Rolling Stone. He even walked off the set of another movie, "The Holcroft Covenant," and was replaced by Michael Caine, per the New York Times.

Caan was also frustrated by the volatility of the industry and his ever-changing public image. Speaking to the Rolling Stone in 1981, Caan said he acted for respect and satisfaction, and not happiness. Yet, each time he re-established his name through good work, he ended up on a tabloid, only to tarnish his progress.

It's hard to think of an actor who missed out on more roles than James Caan. There were some parts he didn't regret rejecting, such as a starring role in Francis Ford Coppola's "Apocalypse Now." Coppola tried convincing him to join the cast, telling him that they would live in Manila and fly to the set on a helicopter, but Caan hated flying and tse-tse flies, per Contact Music. Caan was also concerned about his pay. When bringing the issue up, Coppola waved him away and said that actors were only interested in money, per Rolling Stone. 

And there were roles Caan really did regret passing out on. The first was Milos Forman's classic "One Flew Over the Cuckoo's Nest." Caan rejected the role four times, believing it wasn't "visual" enough, per Contact Music. The part ended up going to Jack Nicholson in a career-defining role, per Mental Floss.

Caan also came to regret rejecting the part of Ted Kramer in "Kramer vs. Kramer," which ended up going to Dustin Hoffman. At the time, he thought of it as "middle-class, bourgeois horsecr*p." He believed both "One Flew Over the Cuckoo's Nest" and "Kramer vs. Kramer" would become box office bombs, per Contact Music. Other roles Caan turned were Gene Hackman's role in "The French Connection," Richard Dreyfuss' role in "Close Encounters of the Third Kind," Han Solo in "Star Wars," and Christopher Reeve's "Superman," per Mental Floss.

In 1981, James Caan's younger sister, Barbra died from leukemia. He was devastated, especially since he considered her to be his best friend. In an interview with The Independent, James said she was the only person he knew that he was "afraid of." Barbra ran his production company, was his assistant for his directorial debut "Hide in Plain Sight," and was a producer's assistant for the film "Thief," per UPI. She had a passionate demeanor with every project she undertook, and James adopted that approach to life after she died. But he also adopted some self-destructive habits, including cocaine usage. James described his drug abuse as a "death sentence."

To make matters worse, James lost his savings due to bad dealings by his accountant, leaving him penniless. Disillusioned, he took a break from acting while trying to piece his life together. During that six-year period James coached his son's baseball team. It was then that he experienced a rude awakening that forced him to quit drugs: His son threatened a drug dealer with a baseball bat and nearly tried to kill him. With the help from a friend's intervention, he entered recovery. His final stint in rehab came in 1996, the same year he married his fourth wife, Linda Stokes, per Cigar Aficionado.

James Caan's attempts to reenter the industry were a struggle. His first film after his hiatus was Francis Ford Coppola's "Gardens of Stone." Caan considered it his official comeback, in which he acted with "hunger and thirst," per The Independent. But according to his interview with The Guardian, Coppola had to go out of his way to get Caan casted in the film. Studios were hesitant to give Caan a second chance, distracted by his reputation and the potential insurance costs. It was then that Caan realized that absence didn't make the heart grow fonder, it just made them assume he was dead.

But "Gardens of Stone” was stymied by Coppola's grief over the death of his son, and Caan didn't have faith in the resulting product. Needing cash, his next project was a sci-fi buddy cop film called "Alien Nation." His only hope was that it was commercially viable, per Roger Ebert. But friends in the industry continued to fight for his reemergence, and he was able to achieve a second chance. Rob Reiner landed him roles in "Misery" and "Honeymoon in Vegas," Warren Beatty got him a cameo in "Dick Tracy," and James L. Brooks got him a part in Wes Anderson's "Bottle Rocket," per The Independent.

In a 1981 interview with Rolling Stone, James Caan said the most tragic aspect of his life was his estrangement from his only daughter, Tara. She was the child from his first marriage to Dee Jay Mattis, which ended in 1966. After its dissolution, he added a room to his home so that his daughter could visit every other weekend. But he said that Tara didn't know he existed, and she only visited once in 10 years. Their relationship consisted merely of the check he sent every month. James was determined that the same wouldn't occur to his next-born son, whose mother he had already divorced.

In 2015, James became embroiled in a custody battle when he advocated for joint custody for his last child while his ex-wife, Linda Stokes, wanted primary physical custody while James would be allowed visitation rights, per E! News. 

Caan had five children from four marriages. His oldest son, Scott, followed in his footsteps and became an actor, regularly starring in the show "Hawaii Five-0." They both starred in the 2009 film "Mercy," which Scott wrote, per People.

James Caan was always a roughhouser from an early age. His favorite pastimes as a child were boxing, bull riding, and getting into neighborhood fights, per The Independent. When Caan once went missing from a movie set, the producer, Ray Stark, suggested that Caan was probably at a nearby alligator farm wrestling an alligator, per the Los Angeles Times. Caan's wild manner was part of his legend, so it should come as no surprise that Caan always found ways to get injured. In 1985, he got into a car crash after driving too fast on a road and hitting a tree. But it probably wasn't his fault; he wasn't drunk and he said his brakes failed on him, per UPI. Then, in 1989, he flew off his Harley-Davidson after a car swerved near him, landing him in the hospital. He wasn't wearing a helmet and suffered four broken ribs, per AP.

Caan also lived out his childhood dreams of being a cowboy while participating as a heeler for team-roping at a rodeo. But it landed him in a tough position when his thumb got caught in the rope and was pulled back to his elbow, nearly tearing it off. He had to present himself to the Queen of England alongside co-star Barbra Streisand with his thumb sticking straight up in a cast, which he said made his hand look like a foam finger, per The Independent.

James Caan's last divorce was a messy one, and according to his court documents, it was leaving him broke. He accused ex-wife Linda Stokes of spending his money to the point where he was forced to act in bad movies in order to recuperate. He was also said to have mounting medical bills and medical problems that he couldn't afford treatment for, leaving him in poor health. This was in addition to the nearly $96,840 he was spending on his son who was in college.

Caan was afraid that his recent acting roles, chosen merely to pay the bills, would ruin the reputation he built for 50 years. One particular role he emphasized in the court document was his part in the low-budget campy horror "Sicilian Vampire." Only 50 people attended its New York City premiere, per Fox News. Caan starred in only three scenes and much of the film's budget went to his paycheck, and the film had an unconventional business model, having been prepaid to its distributor and filmed on a tight budget. Caan wasn't even present for the film's premiere at the dubious Big Apple Film Festival, per Vanity Fair.

At 81 years old, James Caan still had hopes to make a great movie. In a 2021 interview with The Independent, Caan compared himself to Henry Fonda, who hoped to make a great movie before he died. Caan identified with that same lack of satisfaction and with the thirst to do "good character stuff" while he was still physically able to. One of the last challenging roles Caan had was his part in Lars Von Trier's 2003 "Dogville." Caan aspired to make another movie like it and ended his interview with a message to directors that he was ready for another major film.

In a 2021 interview with CBS, Caan said he had no intentions of slowing down. He enjoyed the respect that came with acting, along with the ability to reinvent himself with each role. It's unclear whether Caan was able to achieve his goal in the year since; he passed away on July 6, 2022 (via Twitter). But he very nearly received that role, according to "Uncut Gems" directors Josh and Benny Safdie. The brothers wrote in a Tweet that after Adam Sandler rejected their offer the first time, Caan was the natural successor to take on the role of Howard Ratner (via Twitter).