Why Jackie Kennedy Allegedly Disapproved of JFK Jr.'s Relationship with Madonna

Who: Music icon Madonna and journalist, magazine publisher, lawyer, and political heir, John F. Kennedy Jr.

How it Went Down

The Queen of Pop met the famous ladies’ man at a party in 1985 after playing a concert at Madison Square Garden. Three years later, when she split from her then-husband, actor Sean Penn, Madge and JFK Jr. reportedly began seeing each other on the sly.

There are conflicting reports about how involved the two really were. A friend of JFK’s argued it was little more than a “flirtation” due to their conflicting schedules. “They would try to get together but it was hard because she was on tour and he was working,” the source told People. “They saw each other a few times and they had a flirty and friendly banter but it wasn’t a ‘relationship.’” Product of their “friendly banter,” Madge and JFK gave each other nicknames — she would call him “Johnny” or “Kennedy” and he would later say he started the trend of referring to the pop goddess as just “M.”

However, a 2014 tell-all from Christopher Anderson (The Good Son: JFK Jr. and the Mother He Loved) paints a different and more complicated picture of the affair.

Trouble In Paradise
According to Anderson’s writings, JFK Jr. and Madonna’s affair wasn’t exactly “La Isla Bonita.” Though they kept their relationship under wraps, limiting their public rendezvous to visits to the gym and jogs through Central Park, those closest to the pair knew about them, including Madge’s ex, Penn (to whom she was still legally married). As depicted in Anderson’s book, John Jr. introduced himself to Penn at a party honoring Robert De Niro and was rebuffed by the Fast Times at Ridgemont High star. "I know who you are," Penn replied, telling him, "You owe me an apology."

Complicating matters further, John Jr. was reportedly dating actress Christina Haag at the time of his and Madonna’s affair.

Mama, Don’t Preach

Madonna, considered her generation’s answer to Marilyn Monroe, was (unsurprisingly) not a hit with JFK Jr.’s mom, Jackie Kennedy. Aside from the obvious parallels (the late JFK was rumored to have had an affair with Monroe during his time in office), Jackie wasn’t fond of Madge’s “sacrilegious” (as deemed by the Vatican) use of crosses and other Catholic iconography. Of course, it didn’t help that Madonna signed the guestbook at Jackie’s home as “Mrs. Sean Penn.”

What Happened Next

After the Madonna-JFK affair petered out, People’s “Sexiest Man Alive” reportedly engaged in relationships with Sarah Jessica Parker, Cindy Crawford, and Daryl Hannah before his wedding to Calvin Klein publicist Carolyn Bessette in 1996.

On July 16, 1999, John Jr., Bessette, and her sister Lauren were killed in a plane crash on their way to Martha’s Vineyard. John was piloting the plane when he became spatially disoriented and lost control of the aircraft. The trio was reported missing on July 17, their remains were found days later on July 21.

Madonna has since been romantically linked to many men, including Dennis Rodman, Tupac Shakur, and Warren Beatty.

In 1996 she gave birth to her first child, daughter Lourdes, with then-boyfriend Carlos Leon. She wed British film director Guy Ritchie in 2000, welcoming a son, Rocco, that same year. In 2006, Madge and Ritchie adopted son David, though they filed for divorce just two years later in 2008. Madonna went on to release ten (!) more albums and adopt three more daughters: Mercy James, Estere, and Stelle.