James Caan Had 4 Wives and Filed for Divorce from His Last Wife 3 Times

James Caan lived through four marriages in his lifetime. Although short-lived, they all yielded five adorable children who remain a significant part of his life.

In 2017, James Caan called it quits with his longtime wife, Linda Stokes, after two decades together. Their split was one of the actor's four divorces.

His divorce from Stokes caused the most stir due to the split's circumstances and messy custody battle. Since then, the star never saw fit to tie the knot again, even nearly half a decade later.

James Caan's Short Marriages

In 1961, before Caan's launch to stardom, he married Dee Jay Mathis, with whom he shared a daughter, Tara, born in 1964. Caan and Mathis were together for two years prior to their lovely wedding in front of family and friends.

Unfortunately, their marriage hit rock bottom barely two years after welcoming Tara, with the duo divorcing in 1966. Caan and Mathis were actors in the industry then, but despite their celebrity status, the reason for their split remains unknown.

It took a decade before Caan entered another marriage. In 1976, he married Sheila Marie Ryan, known for her previous relationship with Elvis Presley and for being a Playboy cover girl. She was also an actress, most recognized for "Road House," "Lone Star Blues," and "Hunter."

The pair was blessed with a son, Scott Caan, in the same year, who followed in his parents' footsteps as an actor.

However, Caan's second marriage, like his first, was also short-lived. He and Ryan went their separate ways in 1977. Several years later, in September 2012, Ryan died after a difficult battle with cancer.

Following his second divorce, the legendary actor took a long hiatus from marriage, which lasted for over a decade. In September 1990, Caan found love again and exchanged wedding vows with Ingrid Hajek, having his son as the best man.

Hajek was a model raised in Queens, New York, the same neighborhood where Caan grew up. The couple met through mutual friends and had a controversial marriage. Not only was Caan 20 years older than his bride, but he also reportedly cheated on her with Heidi Fleiss.

Although Caan denied Fleiss' claims, his marriage did not last. After two years and one son, Alexander James, Caan and Hajek called it quits. A year after splitting from Hajek, the icon's eyes caught another love interest, Linda Stokes, a costume designer, with whom he exchanged vows on October 7, 1995.

In 2015, after two decades together, the actor filed for divorce from his fourth wife, citing irreconcilable differences. During their relationship, they welcomed two sons, James Arthur and Jacob Nicholas, during their 20 years together.

James Caan's Complicated Fourth Marriage

While it appears the legend and Stokes enjoyed marital bliss for the longest time before their breakup, that may not be the case. In fact, their marriage's longevity could have been due to conscious efforts by the couple to stay together.

Reports show that before their 2017 divorce, James attempted to divorce Stokes at least two times. He filed for divorce first in 2005, then in 2009.

However, the split never pulled through, as the court filings were dismissed on those two prior occasions. Pulling the plug a third time in 2015 seemed like a lucky shot that eventually saw the light of day.

Stokes and James Caan's Custody Battle

After their divorce, James and his fourth wife were at loggerheads over the custody of their youngest son, Jacob. The messy custody battle resulted from Linda Stokes' desire to have full legal and physical custody of the then-16-year-old child.

James, however, wanted joint custody. Their feud was also more complicated due to the absence of a prenup agreement, and James was unwilling to grant the costume designer rights to his finances.

In return, Stokes demanded spousal support from the actor. Following a heated back-and-forth in the legal feud, the court ordered the actor to pay his estranged ex $3,124 per month as child support until Jacob completes high school.

The court also ordered the payment of $5,000 as spousal support until Stokes remarried or one of them passed away. In addition, the legend was expected to offer $400,000 in back pay to his wife.

The resulting implication on the star's finances was ugly. Caan, who claimed to be paying about $13,000 a month to Stokes, insisted the mandate forced him to keep taking movie roles that he would have otherwise rejected.

According to him, some of these roles did not conform with his Hollywood reputation. Court documents also revealed James' claims that his wife's demands forced him to keep working amid his prevailing medical conditions when he should already retire.

James Caan's Love Life

At one point in his life, Caan felt that the media was more interested in his intimate life than his career. After five decades in the industry, he still had some regrets about his work.

Caan's love life had always been a topic of public interest. In 2003, he revealed that he lived at the Playboy Mansion to get over his divorce. Admittedly, he enjoyed being around women without needing to pay them.

"I used to say marriages were like tornadoes," he said, as the New York Post reported. "There's all this blowing and sucking at the beginning, and at the end, you always lose your house."

After his death, Caan's relationship still made headlines. His ex-girlfriend, Leesa Rowland, came forward and accused the actor of abuse after their mutual friend's death in 1993. Rowland and Caan met the year before when she was 25, and he was 52.

James Caan's Children

James Caan was a father to five children from his four ex-wives. His kids, Tara Caan, Scott Caan, Alexander Caan, James Caan, and Jacob Caan, have grown into adulthood and set a path for themselves.

The icon's eldest son, Scott Caan, followed in his father's footsteps, becoming an actor. Today, he is famous for starring in shows such as "Hawaii Five-0," and "Entourage."