Meet Sean Penn’s famous family: from actor blacklisted father to kids following in his footsteps

Leo, born in 1921 and who died in 1998, was Sean’s father. He was born in Lawrence, Massachusetts, the son of Russian-Jewish immigrant parents; his father, Maurice Daniel Penn, was a Jewish man whose parents emigrated from Merkinė in Lithuania.

He served in the United States Army Air Forces during World War II, and began acting in 1946. He appeared on a series of sitcoms, but was also notable for his directing, including episodes of the original Matlock and Ben Casey.

Leo was forced to stop acting during the Red Scare led by the controversial Senator from Wisconsin Joseph McCarthy, after he refused to accuse others to the House Un-American Activities Committee and was subsequently blacklisted, hence his turn to directing.

In a 2012 personal essay for The Hollywood Reporter reflecting on the unjust turn his career took, Sean wrote: “Based on his support of Hollywood trade unions, a commitment to the same social democracy that had been the legacy of President Franklin Roosevelt and his refusal to give names to the rising neo-Nazi-inspired House Committee on Un-American Activities, he was blacklisted by chicken hawks (among them Ronald Reagan) and barred from working in motion pictures by the same country for which he had risked his life those few short years earlier.”

Eileen, born Eileen Annucci in 1927, was born in the Bronx to Italian-American and Irish-American parents, and graduated from New York University before making her Broadway debut in 1953. She married Leo in 1957, after meeting the year prior while she was performing in The Iceman Cometh at the Circle in the Square Theatre. 

They eventually moved to Los Angeles, while Leo was already blacklisted, and she began her career in acting, among her notable roles being as her own son Sean’s mother in Judgement in Berlin (1988), Parenthood (1989), and The Crossing Guard (1995), which Sean directed.

She died at her home in Malibu, the same neighborhood Sean was raised in, in 2022, a week before her 95th birthday.

Contrary to his parents and younger brother, Michael, 67, who was born in Greenwich Village in New York City, pursued a career as a singer and composer. His 1989 single “No Myth” was a top 20 hit in the U.S., and when his brother Sean hosted Saturday Night Live in 1987, he served as the episode’s musical guest. 

And though he didn’t pursue an acting career, he has created original music for film, including for Paul Thomas Anderson’s Boogie Nights (1997), in which he appears in a cameo role as a recording engineer.

He has been married to singer-songwriter Aimee Mann since 1997, and the pair live in Los Angeles.

Christopher, born in Los Angeles in 1965, began acting when he was 12 years old, making his screen debut in 1979’s Charlie and the Talking Buzzard. Among his notable roles are in Francis Ford Coppola’s Rumble Fish (1983), as Tom Cruise’s best friend in All the Right Moves (1983) and as Kevin Bacon’s best friend in Footloose (1984), and later in Reservoir Dogs (1992), True Romance (1993), and The Funeral (1996).

He was in a relationship with Steffiana De La Cruz from 1993 to 1999. In 2006, when he was 40 years old, he was found dead in his Santa Monica apartment; the primary cause of death was ruled as cardiovascular disease, however a toxicology report, which found Valium, morphine, marijuana and codeine, noted that the prescription drug promethazine with codeine and an enlarged heart were possible contributing factors to his death.

Sean’s kids he shares with Robin, his wife from 1996 to 2010, have followed in the footsteps of their parents and grandparents. 

Dylan, born in 1991, is both an actress and model, who made her acting debut in the 2015 horror film Condemned. She has also appeared in Elvis & Nixon (2016), Night Hunter (2018), and most recently Who Invited Charlie? (2022). 

Hopper, born in 1993, began acting in 2011, among his more notable credits being The Last Face (2016), War Machine (2017), Puppy Love (2020), and The Cleaner (2021). His most recent role was in The Good Mother (2023). 

He has been open about his struggle with substance abuse, particularly an addiction to crystal meth, and has credited his father for helping him overcome it.