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Wealth, charm and good looks weren’t the only things JFK Jr. inherited from his dad – infidelity and a fondness for famous blonde bombshells were also passed down.

They say history repeats itself, but rarely is the repetition as stylish as a politically-connected playboy and sultry pop starlet hooking up. But when JFK Jr. and Madonna were having their how-did-they-ever-keep-it-a-secret affair, the sexy resemblance was obvious: JFK Jr. was to JFK Sr. as Madonna was to Marilyn. Or so says Christopher Andersen, the author who details the romance in his new biography The Good Son: JFK Jr. and the Mother He Loved.

Andersen’s main source on the affair, JFK Jr.’s lifelong friend Billy Noonan, had already spilled the details in a previous book. But this latest look inside the lives of America’s royal son offers another perspective – that of Jackie Kennedy Onassis, who met Madonna at the beginning of the short-lived dalliance.

“Not surprisingly,” writes Andersen, “Jackie was anything but thrilled with this particular liaison. There were many things about Madonna that rubbed Jackie the wrong way, not the least of which was her habit of thumbing her nose at Roman Catholic rituals. Madonna’s use of crucifixes and other Catholic images was deemed sacrilegious by the Vatican, and across the globe she was being condemned as a heretic. Nor did it help when Jackie picked up a copy of Life only to see Madonna dolled up as Marilyn on the cover. “I imagine it was all hitting a bit close to home,” [confided Kennedy family friend Gore] Vidal…”

Of course, the affair was doomed to failure, and not just because John John’s mother couldn’t stand Madonna, her religious politics and her resemblance to Marilyn Monroe. When they met, Madonna was married to Sean Penn and JFK Jr. had a girlfriend. By the time they ended things, JFK Jr. still had a girlfriend, and was carrying on several other high-profile flings, Sarah Jessica Parker among them.

From the files: Madonna playing Marilyn Monroe in a 1985 SNL skit with Terry Sweeney as Ted Kennedy and Randy Quaid as John F. Kennedy.
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