Inside Madonna and Sean Penn’s post-divorce relationship

In the ’80s, Madonna and Sean Penn were the Brangelina or Bennifer of the day. They wed in 1985, per ET, in a ceremony plagued by paparazzi helicopters, according to People magazine. Regardless, the Papa Don’t Preach pop star was so smitten with her then-husband that she even dedicated her entire hit 1986 album True Blue to Penn, writing in the accompanying lyrics, “This is dedicated to my husband , the coolest guy in the universe.” However, media scrutiny plagued their marriage, leading to Penn getting so angry at the paps who were following him and his wife down the street that he threw a few punches and ended up in jail People.

Unfortunately, rumors of spousal abuse also abounded: the predominant one was that Penn allegedly tied the singer to a chair and hit her with a baseball bat, according to The Daily Mail, with the outlet reporting that she was being checked for injuries in Cedars Sinai became hospital. In 2015, the “Material Girl” star denied any abuse on the part of Penn, writing, “Sean never hit, ‘tied up,’ or physically assaulted me.” The Guardian. Despite this, Madonna twice filed for divorce: first in 1987 (subsequently withdrawing the petition) and again in 1989, which stalled.

As such, it may surprise some to learn that their relationship is still filled with love and kind words in the decades since their divorce.

Madonna has said several times that Sean Penn is the love of her life

During her 1991 rock monument Truth or Dare, Madonna admitted that Sean Penn was the love of her life, according to Maker, and the two have gushed over each other despite their 1989 divorce. During a 2018 appearance on The Late Show, host Stephen Colbert asked Penn if he could choose between the Vogue singer and Britney Spears. “Ah, I love my first wife very much. There’s no – you don’t compare these things,” he said with a chuckle. Even Madonna’s bestie, actor Debi Mazar, told Andy Cohen on “Watch What Happens Live” that the “Milk” star was her best friend’s love, according to Us Weekly.

But the love fest after divorce doesn’t end there. They briefly embraced onstage at the VH1 Fashion Awards in 1995 when Madonna won a Fashion Icon Award. They were photographed holding hands in 2016 to raise money for Haiti, per Variety, and the “Like A Prayer” singer even said, “Sean, I love you from the moment I looked at you.” That same year, he moved she took her ex to the stage at her Tears of a Clown show at Miami Art Basel, saying, per The Daily Mail, “I’m still in love with you.”

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And the icing has to be her 2015 Rebel Heart Tour rendition of “True Blue,” the very song she wrote for him during their marriage, with the beaming “At Close Range” star in the audience.

Madonna and Sean Penn have been in love for many years

In 2008, when Madonna and Sean Penn were very much married to other people, they were still flirting with each other. The Daily Mail reported in 2009 that after filming a kissing scene with James Franco for Milk, Penn texted the Like A Virgin singer: “I just popped my cherry kissing a guy. I thought of you. I don’t know why.” This cheeky tease was broadcast when Madonna was married to ‘Snatch’ director Guy Ritchie and Penn was married to ‘The Princess Bride’ star Robin Wright.

Despite their amicable divorce relationship, Madge hasn’t managed to keep it up with her second ex-husband, Ritchie. In fact, the two have rarely been spotted together, despite sharing two sons, Rocco Ritchie and David Banda. In 2020, however, they were both photographed at the same time visiting an exhibition at an art gallery in London, according to The Daily Mail. The artist in question, Rhed, has since been revealed to be her son Rocco’s nickname The Guardian.

Penn, on the other hand, had two children with Wright in 1991 and 1993 before marrying her in 1996, according to People. They eventually divorced in 2010, and since then the Oscar-winner has walked down the aisle for a third time, this time with Australian actress Leila George in 2020. Unfortunately, Penn had to make a third trip to divorce court when their marriage ended just a year later .