Matt Dillon – 56

Matt Dillon rose to prominence as the bad boy all girls loved in the ’80s. His breakthrough roles came in 1980 when he starred in My Bodyguard and Little Darlings, and he became a very popular actor throughout the decade. He achieved worldwide recognition in 1998 when he played in There’s Something About Mary alongside Cameron Diaz, whom he also dated for three years. Since 2002, he has also ventured into directing. Although his salary isn’t as high as it once was, he remains a sought-after name in the acting industry, and in 2018, he starred in The House That Jack Built by Lars von Trier.