#19: His Relationship With Madonna

In the late 1980s, Beatty entered a high-profile relationship with pop superstar Madonna. Their romance coincided with their work on Dick Tracy (1990), in which Madonna played the seductive Breathless Mahoney.

The relationship, though passionate, was short-lived. At the peak of her fame, Madonna had a larger-than-life personality that sometimes clashed with Beatty’s more measured approach. Their brief affair was documented in Madonna: Truth or Dare (1991), where Beatty expressed his distaste for the constant presence of cameras.