55. Annette Bening and Warren Beatty
Movie: Bugsy
Location: Pasadena, Los Angeles
Year: 1991
Warren Beatty and Annette Bening connected a little later in life while starring in the 1991 movie Bugsy. Despite a near two-decade age difference, the couple has thrived for almost 30 years. Despite Warren trying to date Bening previously, their plans had fallen through. That all changed on Bugsy.
Their romance escalated quickly from that point onwards, with Annette welcoming their first child just a month after the movie premiered in theaters. They went on to build a happy life together as two A-listers with plenty of pull in the industry.
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