Matt Dillon – 57, Actor

Matt Dillon started his career in the entertainment industry at the age of 14. He rose to immediate success as a natural-born actor and became the heartthrob of many young women.

Dillon has carved out a niche in the film industry thanks to his charisma, attractiveness, and versatility. He’s also featured in several music videos for well-known musicians and singers and working on several TV shows. After achieving mediocre success in some of his early films, it didn’t take him long to rise to the peak of the performance ladder and into the spotlight. While he is well-known for his film investments, he’s had a series of high-profile relationships. Dillon’s views on marriage seem to have changed as he’s grown older, even though he’s never married. He dated There’s Something About Mary co-star Cameron Diaz in the 1990s and is in a long-term relationship with Italian choreographer Roberta Mastromichele. We are hoping to hear wedding bells soon, fingers crossed!