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Top Sean Penn’s beautiful women: Elizabeth McGovern, Susan Sarandon, Madonna, Robin Wright, Scarlett Johansson, Jewel and Jessica White

by Nicole
March 14, 2011 at 8:21 am

Age doesn’t calm his rage. With a James Dean physique, non-conformist political beliefs and a volcanic temper, this 50-year-old actor is proof that women will never resist a bad boy.

InRumor challenges you to choose the best match for Sean Penn. Voting is open until Sunday.

Elizabeth McGovern

Sean Penn was engaged to actress Elizabeth McGovern in 1984 after they fell in love on set of the movie “Racing with the Moon”. However, it seems Penn’s intensity was too much for her to handle.

“Sean was an important relationship for me,” Elizabeth has said. “But there’s a drama to the way Sean lives every bit of his life. He was the kind of guy who was like, ‘This is my girl, I’ve got to own her.’ It was all dramatics. But it was so exhausting, I couldn’t sustain it.”

Susan Sarandon

Sean Penn had a brief affair with Susan Sarandon in 1984. She has since remained a close friend of his.

Recently, it was reported Susan is dating a younger man, Jonathan Bricklin, 31, a New York hipster who took care of a tennis club.


Penn was married to Madonna from 1985 to 1989. Their relationship attracted a lot of media attention because of domestic violence, fights with the paparazzi and alcohol abuse. Madonna dedicated her third studio album True Blue to Penn, referring to him in the liner notes as “the coolest guy in the universe”.

Sean Penn on his marriage to Madonna: “Had we stayed together, we’d have driven each other mad. But I was just as badly behaved as her. I was an angry young man. I had a lot of demons and I don’t really know who could’ve lived with me at the time.”

Robin Wright

They formed one of Hollywood’s most famous and strongest couples. Sean Penn and Robin Wright divorcing after 41 years sixteen years of common life. Parents of two children, Hopper Jack, 14, and Dylan Frances, 16, said the so inseparable decided to proceed, each in turn.

It’s on the set of Angels of the Night in 1990 that she met “the man of her life.” From their union two children were born: daughter Dylan Frances (1991) and son Hopper Jack (1993). Still very much in love, both parents tie the knot in 1996. To care for her family, the unforgettable Jenny from Forrest Gump stayed away from the spotlight and refused many blockbusters.

“She is a ghost to me now,” Sean Penn said of his ex-wife in an interview with Vanity Fair. “We spent all those years together…. Now she’s just gone.”


Jewel met Sean Penn in 1995 when he asked her to write a song for his movie “Crossing Guard”. Penn found out about her when she first appeared on Conan O’Brien.

She wrote the song “Emily” for the movie and Penn directed the original version of the video for her hit song “You Were Meant For Me”. Jewel always said the two of them were just friends.

Recently, Jewel announced she and husband Ty Murray are expecting their first child.

Jessica White

Penn has been linked with model Jessica White. The Sports Illustrated swimsuit model is 26 years old.

Recently she was arrested on assault charges. White was out in town celebrating her breakup from Penn but she got carried away too much.

Scarlett Johansson

Weeks after announcing her separation from husband Ryan Reynolds, media reports talked about a possible new romance in the life of the 26-year-old actress in the person of actor Sean Penn.

Even though the story has been circulating in the media since January, Scarlett’s rep denied any romantic connection between the two actors in a statement to People: “Scarlett and Sean are not dating – they have been friends for years. Nothing more, nothing less. They have been talking over the last few months regarding Haiti Relief and Scarlett’s upcoming trip to Haiti as Oxfam’s Global Ambassador. ”

What do you think? Who made the best match for Sean Penn?

  • Elizabeth McGovern (2%, 3 Votes)
  • Susan Sarandon (5%, 8 Votes)
  • Madonna (54%, 84 Votes)
  • Robin Wright (29%, 46 Votes)
  • Jewel (1%, 1 Votes)
  • Jessica White (2%, 3 Votes)
  • Scarlett Johansson (7%, 11 Votes)

Total Voters: 156

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