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August 23, 2019

30 Candid Photographs of Madonna and Sean Penn in the 1980s

Back in the ’80s, the relationship between Madonna and a young Sean Penn was highly publicized tabloid fodder.

The year 1985 was a milestone for Madonna in every sense. While Like A Virgin, released in 1984, was still booming thanks to its brave lyrics and controversial video, Madonna was already prepared for a new blast! She wanted to make a fancy video for her song Material Girl which had Marilyn Monroe references. Madonna had already become a master for setting and defining the magazine agenda after all! However something unlooked-for would turn her life around at the studio she went to for her video recording – she would come across Sean Penn and immediately fall in love.

But there was a problem: Madonna and Penn’s close circle of friends doubted something good would come out of these 2 crazies’ get-together! They could both be extraordinary, eccentric characters but Madonna was the ultimate popular icon while Sean Penn was an idealist in solitude who had always causes to fight for. While people around them were busy making such comparisons, these two decided to get married and shock everyone only 3 months after they met!

On the other hand, the couple had their first relationship crisis due to that very obvious issue with their conflicting personalities on the very day of their wedding! Sean Penn was extremely frustrated when 13 media helicopters rushed to the modest wedding in Malibu and Madonna, as much as she loved the attention, had to give up on it.

Madonna’s closest friend Debi Mazar defines the marriage as: “They are vastly happy as long as they don’t have to be “Madonna” and “Sean Penn”. But the moment Sean feels pressured he withdraws and clings to alcohol. This is why they sometimes go through rough times.”

It was actually the way it was. Sean couldn’t find a way out because Madonna’s popularity was becoming excessive to a point where it was impossible for them to walk on the street. Trying to sweep their snowballing marriage issues under the rug, they co-starred in the movie Shanghai Surprise as their last resort, and both their marriage and the movie suffered similarly disappointing ends. Shanghai Surprise was made with great hopes but became a box-office bomb. And the couple ended their 4-year marriage in 1989.


  1. Surprised it didn't work out. Both are crackpots.

  2. Madonna and Sean Penn: Two more reasons to hate the 80s.




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