George Clooney

During the 1990s, Clooney often publicly asserted that he would never get remarried or have any children, but Michelle Pfeiffer and Nicole Kidman both bet $10,000 each that he would be a father before he turned 40. They were both wrong, and each sent him a check. He returned the money, betting double or nothing that he wouldn't have kids by age 50. At age 53, he broke his vows to never marry again when he wed human rights lawyer Amal Clooney (née Alamuddin) in 2014. In early 2017, news broke that the couple were pregnant with twins.

[discussing casting choices Mel Gibson and Nicolas Cage for Tres reyes (1999) before he had signed] Luckily, both those guys were tied and gagged in my apartment, and that was a problem for the casting department.