Madonna: The Beginning

One of Hollywood’s most whirlwind romances began in early 1985 after they met on Madonna’s Material Girl music video set. Their relationship quickly gained traction in the public eye, with the couple marrying on Madonna’s 27th birthday in August 1985.

The marriage marked a collision of two powerful personas: Madonna’s rising fame as the Queen of Pop and Penn’s reputation as a passionate and volatile actor. Their relationship was intense, with both speaking about their strong connection, although their temperamental natures hinted at potential challenges ahead.