14. Rupert Murdoch & Jerry Hall: 25 Years
Two and a half decades fall between media mogul Rupert Murdoch and former-model Jerry Hall. Hall was previously married and had four children with Rolling Stones front-man Mick Jagger, before the couple split in 1999. Murdoch also has children from previous marriages. Despite the previous ties and vast age gap, 60-year-old Hall and 85-year-old Murdoch were married in 2016.