Sean Penn’s Parents Were Celebrated Hollywood Actors Too: Remembering Eileen Ryan and Leo Penn

Sean Penn's family not only had an impact on his acting career but on his social consciousness as well. With a "lioness" for a mother and a war hero for a father, Sean Penn's parents left a mark on him after their passing.

Sean has made a name for himself as one of the most influential actors in the industry for his impressive performances and acting talent. In his early years, he appeared in films such as "Taps" in 1981 and "Fast Times at Ridgemont High" in 1982. His career skyrocketed in the 1990s when fans and critics began to notice and praise Sean.

When Sean was still married to Madonna, they appeared in "Shanghai Surprise." In 1995, he received his first Oscar nomination for "Dead Man Walking." His first Oscar win came in 2003 for "Mystic River." Clint Eastwood directed the movie, and Sean won the Oscar for Best Actor.

Sean's family heavily influenced his successful acting career. His parents, Eileen Ryan and Leo Penn, were not strangers to show business, and Sean recalled drawing great inspiration from his brother, Chris Penn, and his role in "The Funeral."

Who Was Eileen Ryan, Sean Penn's Mother?

Eileen was born in New York City on October 16, 1927, and was of Italian and half-Irish descent. She obtained a science degree from New York University to appease her parents more than anything and jetted to New Orleans to chase her dreams.

Eileen's career began with her singing in bars before she found her way to Broadway, where she became a successful actress. Her acting credits included "Parenthood" in 1989, "Freaks" in 2002, and "Feast," her role most commonly known, in 2005.

She met Leo in 1957 while rehearsing for the play "The Iceman Cometh" in New York City. They moved in after a week of seeing each other and married a few months later.

Eileen chose to leave her acting career behind when she became a mother. Growing up, her father was overly cautious of her, so she dreamed of having sons. Eileen left quite an impression on the three sons she had, Sean and Chris, and their other brother Michael Penn. Sean said:

"She was a lioness. Boy, could she dress down those authority figures. She was unintimidatable."

She encouraged freedom among her sons; Sean recalled a childhood filled with surfing, horse riding, and spending nights on the beach. His childhood consisted of his mother encouraging him and his brothers to broaden their imaginations.

And alongside her fiery personality came her brutal honesty. After making his debut performance at the Group Repertory Theatre in North Hollywood, according to Sean, Eileen grabbed his face, looked him in the eye, and said, "You were terrible."

Despite this, Sean said Eileen was his greatest source of confidence. And out of all of her sons, she was tougher on Sean as he was more like her. She inspired Sean's reputation for questioning injustices, and when asked if she was fantastic, Sean replied, "I would say that lovingly, but I do confirm it as such."

Eileen passed away in 2022, a week before her 95th birthday, in her home in Malibu. Michael took to social media and shared the news of his mother's passing, and Eileen's representative also confirmed the news.

Despite having known each other briefly before tying the knot, Eileen said she and Leo shared a "great marriage" and further added:

"We were never bored with each other. We grew together."

Who Was Sean Penn's Father, Leo Penn?

Leo was born on August 27, 1921, in Lawrence, Massachusetts. He was an actor and a director, and he had commonly known roles in "Ben Casey," "The Mississippi," and "Remington Steele."

Leo was also a pilot in the Second World War. He flew thirty-one missions and received a Distinguished Flying Cross and the Air Medal. The war took a toll on Leo, and Sean recalled his father's experience with "hardcore flashbacks and sleeplessness."

Leo was blacklisted in the 1940s and 50s, and his military career influenced Sean and his rebelliousness. Whenever he thinks of his father, the memory of the glimmer in Leo's eyes stuck with him. Sean said:

"He could have very strong opinions and see all sides of an issue at the same time, but there was always that sparkle thing."

Leo's work kept him busy, and Sean said he was a "good weekend father." He spent time with his sons on the weekends, and his spare time during the week was dedicated to his wife.

Sean recalls moments of sneaking for a late-night snack and stumbling across his parents lovingly embracing on their home porch in Malibu, looking out at the Pacific.

Leo died on September 5, 1998, at St. John's Health Center in California. He was 77 at the time of his passing and died from lung cancer. His close friend, Ernest Frankel, said Leo was a wise man who was always looking to make "the most pedestrian material as good as it can be."

Sean Penn's Brothers, Chris and Michael

Chris was another member of the Penn family to pursue an acting career. Born on October 10, 1965, in Los Angeles, California, he began acting when he was 12.

He and Sean made shorts in high school, and in 1979 he made his onscreen debut in "Charlie and the Talking Buzzard." Chris lived a lifestyle that ultimately led to his death.

During an appearance with Larry King, Sean said although Chris died of natural causes, his drinking, substance use, and weight played a significant role in his passing. Not only were the brothers very close, but Chris also inspired Sean's career. Chris's death took a toll on Sean, who said:

"It's a piece of you. I'm one of three, so I'm either my right, left arm or the center at various times, and each was the other, so I intermittently have lost my right arm, the left or in the center."

Sean Penn's remaining brother, Michael, is a musician and composer. He was born on August 1, 1958, in New York City and won the 1990 MTV Video Music Award for Best New Artist for his first single, "No Myth." He shifted to film scoring and married Aimee Mann on December 29, 1997.