Out of all the women JFK Jr. was linked to, Madonna was undoubtedly the most “controversial.” Not just because, to Jackie O, she represented a modern Marilyn (complete with imitating her in the video for “Material Girl”), but because, at the time when they were reported to have had a “dalliance,” Madonna was still married to Sean Penn. Not that it seemed to bother JFK Jr. or Madonna, both of whom were, by that point, used to seeing something they wanted and taking it.
The mutual fascination between the two was both natural and inevitable. After all, she was the Marilyn of the 1980s, and he was the son of JFK. It was only “right” to explore one another and continue a certain politics-meets-pop culture tradition (arguably started by John F. Kennedy when he had an affair with Marilyn). Which is why the following line delivered by Paul Anthony Kelly (who plays JFK Jr.) in the first episode of Love Story is so telling: “I just think that if anyone can bridge the divide between politics and pop culture, it’s me.” This said to his cousin, Anthony Radziwill (Erich Bergen) in the locker room of New York Athletic Club (though, of course, the filming instead took place at Equinox, proving the exclusivity factor of NYAC).
Madonna likely felt the same way, flirting with the political at a time when liberals like herself were fed up with a conservative codger like Ronald Reagan calling the shots. Besides, if she could get a decent fuck out of it, why not? And from the rumors that swirled about their relationship—nay, affair—it sounded very sizzling indeed. With one such rumor positing that JFK Jr. liked to spread peanut butter on her legs (presumably the inner legs closer to a certain “nether region”). A speculation that prompted Madonna to quip, “Do you know how many calories there are in peanut butter? Low-fat whipped cream, yes, but not peanut butter.”
As for how and when the two first met, accounts vary (as they also do for how and when Carolyn Bessette met John), though the most common one is that their paths first crossed in 1985 at a party. Or was it backstage at one of The Virgin Tour dates at Madison Square Garden (for, yes, there exists a photo of JFK Jr. posing with Keith Haring and Fab Five Freddy)? Wherever it might have been, 1985 seems to be the definitive year they met. And it was also, incidentally, the same year Madonna met Sean Penn, who was brought to the set of her “Material Girl” video, either because of Meegan Lee Ochs (his personal assistant) or director Mary Lambert, depending on who one asks.
As legend has it, the two locked eyes while she was still dressed in her Marilyn regalia and it was apparently love (or lust) at first sight. At least until Penn started to show signs of his volatile temper (especially when it came to the paparazzi). In fact, Madonna initially filed for divorce at the end of 1987, only to withdraw the papers roughly two weeks later and keep soldering on in the marriage until 1989. Though, funnily enough, it seemed pointless for her to have bothered when taking into account that her “peak affair years” with JFK Jr. were 1987-1988, with Jackie O taking it seriously enough to attend one of Madonna’s 1988 performances in Speed-the-Plow, a play written by David Mamet. Granted, Jackie wasn’t willing to go backstage and actually speak to Madonna, for she felt that would have been too big a sign, on her part, that she somehow “approved” of the relationship.
While accounts also vary as to the definitive “why” behind their breakup, the biggest speculation is that it was a union Jackie never would have sanctioned (then again, there are few unions she would have between any other woman and her son). Though, somehow, that didn’t prevent John from later reportedly asking Madonna to pose for the cover of George…as Jackie (you know, the way he asked Drew Barrymore to pose as Marilyn for the September 1996 issue). Obviously, Madonna declined the “offer.” Even so, the two seemed to remain on “friendly” enough terms, at least as of 1997, when Madonna and JFK Jr. were photographed a few times together at the same infamous boxing match: “The Bite Fight” a.k.a. Evander Holyfield vs. Mike Tyson on June 28, 1997. And despite the brevity of their affair, it’s clearly managed to hold the interest of the public consciousness, with Love Story: JFK Jr. and Carolyn Bessette reigniting it all over again.
Indeed, from the very first episode, Madonna’s affair with “John John” is alluded to when he’s at Central Park about to play some football with a group of friends. Clocking the presence of the paparazzi, one of his “chums,” Colin (Aaron Dean Eisenberg), ribs, “Let’s go easy on John, all right? Can’t have America finding out their favorite son has butterfingers.” This prompts John to respond, “Eat my ass, Colin.” Not missing a beat, Colin retorts, “Hey, I’d love to go where only Madonna’s gone before.”
Then, in episode four, titled “I Love You,” as if wanting her to continue hovering over the series (and the 90s at large) like a specter, it opens with Madonna’s lead single from Bedtime Stories, “Secret,” playing as two women steal a poster of Kate Moss’ Obsession ad (a testament to what a phenomenon she had become as a result of that Calvin Klein campaign). As they run down the sidewalk, JFK Jr. walks past them and into Indochine where the paparazzi wait outside to take pictures of people like him going in (something that would be abhorrent to Chappell Roan). To be sure, patrons like Madonna herself could often be found at Indochine in its heyday. With M’s presence there immortalized by some paparazzi snaps of her there in 1989 for a charity event.
Of course, Madonna’s clout didn’t stop when the 80s did, with her pervasiveness only ramping up right as the 90s started thanks to “Vogue” and the Blond Ambition Tour. Which is part of why, in the sixth episode, “The Wedding,” Carolyn (Sarah Pidgeon) does a mocking version of voguing as she brings up Madonna on John’s endless list of exes by guessing her name as one of the potential “former flames” that John is referring to when he says he’s been to Cumberland Island “once” before. Mentioning this detail to her because he’s also suggesting it as the secluded, incredibly private location where they should have their wedding (and eventually do).
When he confesses the name of the ex to be Christina, the show goes no further at referring to the ultimately fraught five-year relationship JFK Jr. had with Christina Haag, the first girlfriend he exposed to the dangers of his ostensible death wish. Whereas Carolyn, of course, would be the last to experience it—dead at JFK Jr.’s reckless hands. The twist of irony being that he was the one with the bum foot at the time of the plane crash, while Christina had the bum foot when he asked her to go kayaking with him in unsure Jamaican waters while the pair were on vacation together.
In fact, maybe the one girlfriend that John Jr. could never convince to do anything reckless would have been Madonna, one of the few people in America with more power, influence and public interest than he had when they were “dating.” In the end, one might say this was truly what caused their breakup rather than anything Jackie might have had to say about their, er, coming together.
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