Fred Astaire – Robin Smith
Age Difference – 45
Tony Curtis – Jill Vandenberg
Age Difference – 46
Dick Van Dyke – Arlene Silver
Age Difference – 46
Cary Grant – Barbara Harris
Age Difference – 47
Anthony Quinn – Kathy Benvin
Age Difference – 47
Tony Randall – Heather Harlan
Age Difference – 51
Hugh Hefner – Holly Madison
Age Difference – 54
Hugh Hefner – Crystal Harris
Age Difference – 60
J. Howard Marshall – Anna Nicole Smith
Age Difference – 63
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