Special Encounters #3: Madonna & Sean Penn

Now this is one of the coolest couples ever – a couple who people born in 90’s and after would be awed to know were once married. Even more radiant than when on stage in every scene they are together, this couple is none other than the inarguably ultimate Pop Queen Madonna and the Hollywood rebel Sean Penn!

Love combined with admiration, a passionate relationship, a sudden marriage and of course a fierce breakup… This couple had lived every phase to the fullest, however, what makes Madonna ve Sean Penn an interesting couple for us is their unbreakable bond for 28 years – and counting.

Material Girl vs Poison Penn

Born to a devout Catholic family of Italian descent, Madonna (Madonna Louise Ciccone with her full name) was a so bold young woman to reject her family values and come to New York (City) with only 35 dollars in her pocket. Being totally broke while job-hunting on the streets of New York (City) didn’t kill her spirit nor determination, and she had already signed her first singles deal in her 3rd year after moving there. Spreading her popularity worldwide with her sensational single Like A Virgin, released in 1984, Madonna started living the golden era of her time by the mid of 80’s.

Madonna was so fond of being under the spotlights, receiving applauses and attention that she even turned down the dance scholarship she sweated so hard for and jumped right in the music industry as a self-educated pop singer. Young Maddy was climbing the ladder to stardom pretty fast, however behind all her impulsive decisions and marginal attitude one could feel the shadows of an oppressive father figure.

“I would never restrain myself into a single life” said Madonna, as the true symbol of freedom for the era’s young women. She was getting more and more popular with her song, Material Girl.

While Madonna was becoming the diva of new generation, Sean Penn – a.k.a. Poison Penn – made his way into the top of the badass&handsome list after Bad Boys, his breakout movie in 1983. Penn was also of Italian descent and freedom meant everything to him. Living like a true “neighborhood lad” and having had dealt with the concepts of “corrupt system” and “power abuse” all his life, the talented actor had already gained his reputation as another Hollywood’s “badass” actor.

Two “crazies” together doesn’t seem like a good idea

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! (No matter what they say we LOVE this type of encounters and burst with joy once Pub Story enables them :))

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.

Breakups are part of love

Don’t think it’s over because this is where the actual story starts. Because the Pub Story philosophy says even the most tragic separations and ends mean new stories are awaiting at your door! Let’s carry on with our story:

Upon breaking up Madonna had a more difficult time than Penn pulling herself together. She even couldn’t let anyone into her life until 1994 when she met Carlos Leon, the father of her daughter. Madonna was still at the top of the list when she married the British director Guy Richie – her second marriage 6 years after Leon. Meanwhile Penn, both an in-demand Hollywood actor with 2 Oscar rewards and a family man, was happily married to Robin Wright.

But then, “it” happened in 2011. Many years later after one of her concerts, Madonna and Penn were seen together and although the news fell like a bombshell, they admitted never losing touch in all those years. Addressing Penn as “the love of her life”, Madonna mentioned they used every opportunity to see each other.

Having gotten together in a few charity nights and spotted in intense scenes together, the couple obviously remains the way they have always been: Madonna shouts out her love for Penn in front of cameras, while Penn only wearing his signature timid smile, without a word. But sometimes you don’t need to put everything into words, do you?

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