But despite pursuing interests that were far from those of his father – namely avoiding politics – the pressure of being the president’s son was not an easy legacy to shake. “He called me once and said, ‘Everyone expects me to be a great man, but even my father was no model – and I think it would be a much more interesting challenge to see if could make myself into a good man,” friend John Perry Barlow told the documentary I Am JFK Jr.
Like his father, John Jr had a penchant for glamorous girlfriends.
Brooke Shields, Cindy Crawford, Sarah Jessica Parker, Madonna and Daryl Hannah all dated JFK Hr at one point or another, providing valuable fodder for the tabloids.
"He was a public domain kind of guy," Sarah Jessica Parker told The New York Times in 1992 after they split. "I never had any idea of what real fame was until I met John."
In 1995 John Jr hedged his bets of publishing, starting George magazine, a glossy monthly that bridged the gap between politics and the people. The daily running of George signalled a period of stability for the playboy, which was further bolstered when he started dating Carolyn Bessette in 1994.
Carolyn was a publicist for Calvin Klein and the pair, who ran in similar New York circles, fell hard and fast. By 1996, Carolyn and John were married in a secret ceremony. A recent documentary The Last Days of John F Kennedy Jr examined the pressure the couple were under.
“They were under an enormous, bright spotlight and that had to be hard to cope with, particularly for her,” says ABC News correspondent Deborah Roberts. “It think it was very difficult for him watching her have to deal with this immense scrutiny.”
Tragedy strikes again
Since he was a young boy, John Jr had dreamed of being a pilot. By 1996 he had logged more than 300 flying hours, although only 55 of those hours had been at night.
On the evening of July 16, 1999, John Jr was due to attend the wedding of his cousin, Rory. Joining him in his six-seat Piper Saratoga plane were wife Carolyn and her sister Lauren. They were headed for Martha’s Vineyard in rain, wind and fog. Tragically, they never made it.
The last official radar signals from the plane came in at 9.34pm. Owing to the treacherous weather, John Jr is thought to have suffered spatial disorientation. Consumed by panic in the cockpit, he piloted the aircraft into the depths of the sea, and it ripped apart on impact.
WHO’s special collector’s issue, The Kennedys, takes you inside the lives of America’s first family, from JFK, Jackie, Bobby and John Jr. Out now.