Warren Beatty and Annette Bening – 21 Years

Warren Beatty may come across as a sweet old man, but in his heyday, he was quite the lady’s man. In fact, he has a long list of female partners that is rumored to number in the 100s. That all ground to a halt when he met actress Annette Bening, whose attention he has been vying for ever since.

What’s most amazing is that, despite his reputation, Bening has held her own with Beatty, despite the massive 21-year age gap between them. They got married in 1992 and have four children together. Bening appeared in an episode of “Stars in the House” in 2021.