Sean has been married to Leila since last July, but the actor has had two previous marriages, to actress Robin Wright and superstar Madonna.
First marriage: Robin Wright 1996 to 2010
First marriage: Robin Wright 1996 to 2010
Sean was married to House Of Cards actress Robin Wright, 55, for 14 years.
The former couple share two children Dylan, 30, and Hooper, 28.
They had an on-and-off marriage and he had first filed to divorce the actress in December 2007 before they reconciled five months later.
In April 2009 the actor filed for divorce again, before he withdrew the motion just one month later.
However in August of that year, Wright filed for divorce and court records show that they were officially ruled divorced less than one year later, on July 22, 2010.
Second marriage: Madonna 1985 to 1989
Sean was married to Material Girl singer Madonna for four years.
He has spoken about always having a special place in his heart for the star, saying in a 2018 Stephen Colbert appearance ‘I love my first wife very much.’
Second marriage: Madonna 1985 to 1989
In 2016 Madonna confessed that she was ‘still in love’ with the actor and jokingly offered to re-marry him if he paid $150,000 to her charity.
When she filed for divorce she cited irreconcilable differences.
Prior to their wedding she seemed to think it was headed for trouble: ‘His temperament is also similar to mine. That doesn’t always make for ideal relationships, but I don’t know what will happen.’
The relationship was plagued by physical and emotional abuse, and she sought psychiatric help after the wedding.
In June 1987 he reportedly hit her across the head with a baseball bat but she refused to press charges.
Two years later she filed a police report after he scaled their Malibu home and told her he owned her ‘lock, stock, and barrel,’ and then proceeded to physically terrorize her, leaving her with injuries including a busted lip.
Penn was charged with felony domestic assault, but Madonna told the DA to drop the charges against him, though he eventually pleaded guilty to a misdemeanor. They split shortly thereafter.