In 1984, when Penn was on the set of Racing with the Moon, he met Elizabeth McGovern. Elizabeth McGovern is an actress from United State. She is also a musician. Few months later, they got engaged. Their engagement was dissolved within short period of time.
In February 1985, Penn met his first wife Madonna. Madonna is a renowned singer and songwriter from United States. She is also a businesswoman. After dating her as his girlfriend for several months they got married on 16th of August 1985. She once named him as the coolest guy in the universe but she filed for divorce at the end of 1987 and they finally got divorced on 14th of September 1989. He also served 60 days in jail in the late 1980s.
After Penn dissolved his married life, he was spotted with Robin Wright having romantic love affairs with each other in 1989. From this romantic love life, they also had daughter in 1991 and they got married on 27th of April 1996. They got divorced on 4th of August 2010.
In the late 2013, Penn began dating Charlize Theron. Charlize Theron is also a beautiful and talented actress from United States. They got engaged in December 2014 but this engagement was called off after few months.
Penn was enrolled at Santa Monica High School. He was also interested in film making at a young age and began making short movies with his childhood friends. In 1974, he starred the kid role in the TV series Little House on the Prairie. Half a decade later he starred the role of Sam in the TV series Barnaby Jones. In 1981, he made his bog screen debut by starring the role of Cadet Capt. Alex Dwyer in the movie Taps. His breakthrough role as an actor came in 2003 after he portrayed the role of James "Jimmy" Markum in the movie Mystic River. At the end of 2002, he criticized President Bush to end a war of terror against Iraq. For this role in I Am Sam, he earned the salary of $5,000,000. His net worth is $150 million.