Sean Penn, Madonna, and the Surprise that Didn't Quite Succeed

Charlize Theron dated Sean Penn for a year and a half. ๐Ÿ’ž

Charlize Theron dated Sean Penn for a year and a half. ๐Ÿ’ž

Rock teamed up with Sean Penn for a film about...unity?๐Ÿ‘Œ

Rock teamed up with Sean Penn for a film about...unity?๐Ÿ‘Œ

In 2008, Sean Penn became the first westerner ever to be granted an interview with Raรบl Castro.

In 2008, Sean Penn became the first westerner ever to be granted an interview with Raรบl Castro.

Sean Penn insisted on Volodymyr's appearance at the Oscars! ๐Ÿ†

Sean Penn insisted on Volodymyr's appearance at the Oscars! ๐Ÿ†

Sean Penn made his directorial debut with 'The Indian Runner' in 1991. ๐ŸŽฌ

Sean Penn made his directorial debut with 'The Indian Runner' in 1991. ๐ŸŽฌ

Sean Penn won the Academy Award for his role in the mystery drama 'Mystic River'. ๐Ÿ†

Sean Penn won the Academy Award for his role in the mystery drama 'Mystic River'. ๐Ÿ†

Sean Penn won his second Oscar for Best Actor for 'Milk'. ๐Ÿณ๏ธโ€๐ŸŒˆ

Sean Penn won his second Oscar for Best Actor for 'Milk'. ๐Ÿณ๏ธโ€๐ŸŒˆ

Penn launched his film career with 'Taps' in 1981. ๐ŸŽฅ

Penn launched his film career with 'Taps' in 1981. ๐ŸŽฅ

The controversial actor was also critical of the #metoo movement. ๐Ÿ’ฅ

The controversial actor was also critical of the #metoo movement. ๐Ÿ’ฅ

Sean Penn interviewed "El Chapo" in 2015 and would have faced legal threats as a result if drug lord had not later been captured. ๐Ÿ’ฌ

Sean Penn interviewed "El Chapo" in 2015 and would have faced legal threats as a result if drug lord had not later been captured.  ๐Ÿ’ฌ

In 1985, Sean Penn married the pop icon Madonna. ๐Ÿ’’

In 1985, Sean Penn married the pop icon Madonna. ๐Ÿ’’

Sean Penn went to Ukraine at the beginning of the conflict to work on a documentary. ๐Ÿ‡บ๐Ÿ‡ฆ

Sean Penn went to Ukraine at the beginning of the conflict to work on a documentary. ๐Ÿ‡บ๐Ÿ‡ฆ

At their 1985 wedding, she and Sean Pen could barely hear their vows!๐Ÿ‘ฐ

At their 1985 wedding, she and Sean Pen could barely hear their vows!๐Ÿ‘ฐ

The actor and his crew had to make a quick escape to Poland! ๐Ÿ‡ต๐Ÿ‡ฑ

The actor and his crew had to make a quick escape to Poland! ๐Ÿ‡ต๐Ÿ‡ฑ

Sean opened up about his private meeting with Volodymyr Zelensky in March. ๐Ÿค

Sean opened up about his private meeting with Volodymyr Zelensky in March. ๐Ÿค

Sean Penn's mom had her hand in Jack Nicholson's mouth. ๐Ÿ˜…

Sean Penn's mom had her hand in Jack Nicholson's mouth. ๐Ÿ˜…

Omar admires Sean Penn! ๐Ÿ™Œ

Omar admires Sean Penn! ๐Ÿ™Œ

Check out more celebrity profiles of Rising Stars and superstars like Jojo Siwa, Michael Strahan or Jimmi Simpson. Find fun facts about their age, birthday, star sign, height, relationships and career highlights. Scroll through categories like Business and TV or discover more Actors that are shaping todayโ€™s Movies.

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