10 Hollywood Couples With the Biggest Age Gap

Warren Beatty and Annette Bening

Warren Beatty used to be known as one of the biggest playboys in Hollywood, dating actresses like Natalie Wood and Joan Collins – and even pop singer Madonna at one point. Few thought he'd ever settle down, but when the Academy Award-winning actor met Annette Bening while filming "Bugsy" in 1991, everything changed. Despite being 54, 21 years older than the "American Beauty" star, the couple married the following year, went on to have four children, and have been together ever since.