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But for all this, he liked to act rough-edged: drinking, swearing and riding motorbikes.
At 24, he was two years younger than Madonna, and they discovered that their birthdays were a day apart. Madonna's brother Chris noted: 'He is a dead ringer for our father as a young man, and is middle class like Madonna, but with a street kid persona.
Penn told her he owned her 'lock, stock and barrel'.
When she told him she was leaving the house, he tried to bind her hands with an electric lamp and cord.
Madonna was playing a missionary, Gloria Tatlock, and Penn a conman who was her love interest. It was one of the few outright disasters of Penn's career.
The pair fought openly throughout over how the movie should be made - both with each other and the director. The publicist quit after two days, saying: 'Penn is an arrogant little creep, and his wife goes along with him.' Former Beatle George Harrison, whose company was producing the movie, reportedly had to fly out to Hong Kong to tell them to grow up and start behaving.
What followed was a nine-hour ordeal which left her deeply shaken.
Though she saw lawyers about getting a divorce, she hung on for a full year to see if it could be saved. In the late afternoon of December 28, 1989, Penn scaled the wall surrounding the Malibu house and found Madonna alone in the master bedroom.