Even at his centennial (and 17 years after his passing), Frank Sinatra is still as charming as he was in his prime. Unsurprisingly, the star crooner’s love life was far from dull, with four marriages and a slew of relationships with Old Hollywood icons. Here, BAZAAR lists 25 women with a charm of their own, who were involved with Sinatra in both in real relationships and rumoured flames.

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#1. Lana Turner

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#2. Nancy Barbato

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#3. Donna Reed

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#4. Ava Gardner

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#5. Marilyn Monroe

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#6. Marlene Dietrich

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#7. Judy Garland

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#8. Gloria Vanderbilt

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#9. Joan Crawford

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#10. Grace Kelly

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#11. Natalie Wood

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#12. Lauren Bacall

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#13. Hedy Lamarr

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#14. Shirley Maclaine

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#15. Gina Lollobrigida

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