The Sad Truth About Madonna And Sean Penn's Relationship

On January 5, 1989, Madonna filed for divorce (via The Things) for the second time from actor Sean Penn after less than four years of marriage. Citing irreconcilable differences, the Material Girl put an end to a marriage that ran rife with insecurity, jealousy and even jail time (via Cheat Sheet). 

Back in January of 1985, while filming the music video for the second single off her landmark album "Like A Virgin," Madonna met Penn on the set of "Material Girl." According to Song Facts, Penn was visiting his former assistant Meegan Lee Ochs, who was working on the set for the music video at the time. As legend has it, Penn got his first glimpse of Madonna, decked out in the dress Marilyn Monroe made famous in the film "Gentlemen Prefer Blondes." It was love at first sight for the pair, who decided to tie the knot just six months later on the singer's 27th birthday (via Cheat Sheet). Love was in the air as the couple appeared in the movie "Shanghai Surprise" together in 1986, as well as Madonna dedicating her album "True Blue" to her recent bridegroom that very same year. However, things clearly were not as their public personas led on to be.

Jealousy became a major problem in their relationship, with Penn reportedly breaking out in random fits of rage (via The Things). In fact, according to Cheat Sheet, Penn manhandled songwriter David Wolinski because he thought he saw the songwriter kiss Madonna. Penn's insecurities got so bad, he believed that Madonna was having an affair. According to People, Penn insisted that Madonna was cheating on him with singer Nick Kamen, who was recording the song "Each Time You Break My Heart" with Madonna at the time. The Material Girl vehemently denied the allegations.

In June of 1987, Penn was sentenced to 60 days in jail, due to two probation violations (via People). Even though the actor only served 33 days of the sentence, the strain was still too much for the relationship. Madonna filed for divorce that December, but ended up withdrawing the action. And while rumors of physical abuse ran rampant over the course of their marriage, Madonna outright said all the allegations of abuse were indeed false (via Cheat Sheet). Still, the damage had been done. In January of '89, Madonna filed for divorce from Penn for the second time, and this time it stuck. While her reasoning for the divorce was "irreconcilable differences," both have gone on record to say that they were still in love with each other, with Madonna admitting her love for Penn in 1991's documentary "In Bed With Madonna" and Penn doing likewise in 2015 on "The Late Show With Stephen Colbert" (via Cheat Sheet).