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Hugh Hefner and Kimberley Conrad

Hugh Hefner

The Playboy magazine founder fathered a son, Marston Glenn, on his 64th birthday in 1990 while he had another son, Cooper Bradford, just a year later to his second wife, 1989 Playmate of the Year Kimberley Conrad, now 47.

Julio Iglesias

Julio Iglesias

The Spanish singer had his eighth child, Ruth, in 2006 at age 63. But his father, Dr Iglesias Puga, had the singer's half-brother Jaime at the age of 89. His partner at the time Ronna Keitt was expecting their second child when he died suddenly at the age of 90. According to reports, Baby Ruth was born on what would have been his 91st birthday.

John Simpson

John Simpson

The BBC's World Affairs Editor had a son, Rafe, aged 61 with his wife Dee.

Rupert Murdoch and Wendi Deng

Rupert Murdoch

The Australian-born media mogul has two children, Grace, 8, and Chloe, 6, with his third wife, Chinese-born News Corp executive Wendi Deng. When the pair married in 1999 he was 68, she 32.

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（來源：telegraph.co.uk  編輯：Julie）