Hollywood actors

Remembering Eileen Ryan and Leo Penn

Sean Penn’s family not only impacted his acting career, but also his social conscience. With a “lioness” for mother and a war hero for father, the parents of Sean Penn marked him after their death.

Sean has made a name for himself as one of the most influential actors in the industry for his impressive performances and acting talent. During his early years, he appeared in films such as “Taps” in 1981 and “Fast Times at Ridgemont High” in 1982. His career exploded in the 1990s when fans and critics began to notice and for rent 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 film and Sean won the Best Actor Oscar.

Sean Penn and his mother Eileen Ryan at the 76th Annual Oscar Nominees Luncheon | Source: Getty Images

Sean’s family strongly influenced his successful acting career. His parents, Eileen Ryan and Leo Penn, were no strangers to show business, and Sean recalled getting a lot of 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 on October 16, 1927 and was of Italian and half-Irish descent. She got a science degree from New York University to appease her parents more than anything and flew to New Orleans to pursue her dreams.

Eileen’s career began singing in bars before finding her way to Broadway, where she became a successful actress. His acting credits include “Parenthood” in 1989, “Freaks” in 2002 and “Feast”, his best-known role, in 2005.

Eileen Ryan at the premiere of "Milk" on November 13, 2008 in California |  Source: Getty Images

Eileen Ryan at the premiere of “Milk” on November 13, 2008 in California | Source: Getty Images

She met Leo in 1957 while rehearsing for the play “The Iceman Cometh” in New York. They moved in after a week of dating and got married a few months later.

Eileen chose to give up her acting career when she became a mother. Growing up, her father was too careful with her, so she dreamed of having sons. Eileen left a strong 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 disguise those authority figures. She was intimidating.”

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

And alongside his fiery personality came his brutal honesty. After debuting at the Group Repertory Theater 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 most trusted source. And of all her sons, she was the hardest on Sean because he looked more like her. She inspired Sean’s reputation for questioning injustices, and when asked if she was fantastic, Sean replied“I would say that with love, but I confirm it as such.”

Eileen died in 2022, a week before her 95th birthday, at her Malibu home. Michael took to social media and shared the news of his mother’s passing, and Eileen’s rep also confirmed the news.

Although they briefly knew each other before getting married, Eileen said she and Leo shared a “great marriage” and furthermore added:

“We were never bored with each other. We grew up together.”

Leo Penn and Eileen Ryan at the premiere of "Point Blank" on April 17, 1986 in New York |  Source: Getty Images

Leo Penn and Eileen Ryan at the premiere of “At Close Range” on April 17, 1986 in New York | Source: Getty Images

Who was Sean Penn’s father, Leo Penn?

Leo was born on August 27, 1921 in Lawrence, Massachusetts. It was an actor and a directorand he had known roles in “Ben Casey”, “The Mississippi” and “Remington Steele”.

Leo was also a pilot during World War II. He flew thirty-one missions and received a Distinguished Flying Cross and the Air Medal. The war took its toll on Leo, and Sean recalled his father’s experience with “hardcore flashbacks and insomnia”.

Leo was blacklisted in the 1940s and 50s, and his military career influenced Sean and his rebellion. Every time he thinks of his father, the memory of the glint in Leo’s eyes stays 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 this shiny thing.”

Leo Penn et al October 20, 1994 |  Source: Getty Images

Leo Penn et al October 20, 1994 | Source: Getty Images

Leo’s job kept him busy and Sean said he was a “good weekend dad”. He spent time with his sons on the weekends and his free time during the week was spent with his wife.

Sean recalls times he snuck out for a late-night snack and stumbled upon his parents lovingly kissing on the porch of their Malibu home, gazing 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 death and died of lung cancer. His close friend, Ernest Frankel, said Leo was a wise man who always sought to make “the most walkable material as good as possible”.

Sean Penn’s brothers, Chris and Michael

Chris was another Penn family member to pursue an acting career. Born on October 10, 1965 in Los Angeles, California, he started to act when he was 12 years old.

Chris Penn in New York on September 30, 1993. |  Source: Getty Images

Chris Penn in New York on September 30, 1993. | Source: Getty Images

He and Sean made short films in high school, and in 1979 he made his screen 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 that although Chris died of natural causes, his drinking, substance use and weight played a large role in his passing. Not only were the brothers very close, but Chris also inspired Sean’s career. Chris’ death impacted Sean, who said:

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

Sean Penn’s remaining brother, Michael, is a musician and composer. He was born August 1, 1958 in New York City and won the 1990 MTV Video Music Award for Best New Artist for his debut single, “No Myth.” He passed to movie soundtrack and married Aimee Mann on December 29, 1997.